Momentum - Fourth Quarter 2016

4th Quarter 2016

National Lloyds

Nevada Growth Nevada is proving to be a potential high-growth market for National Lloyds Corporation. The Texas-based property and casualty insurance provider is expanding its physical presence in the state, which until recently has gone largely untapped.

“We believe Nevada offers growth opportunity for the company with less volatility, as the region has little catastrophe exposure,” said Bob Otis, National Lloyds Corporation CEO. To drive performance, National Lloyds added a Nevada marketing representative position over the summer and is in the process of increasing the number of agents and

offices in the state. The company is also planning product enhancements for 2017, which it anticipates will spur further growth in the region.

MOMENTUM A Hilltop Holdings Publication

Since 1948, National Lloyds Corporation has been working to make life easier for its customers, providing property and casualty insurance through its two underwriting companies: National Lloyds Insurance Company and American Summit Insurance Company. Headquartered in Waco, Texas, National Lloyds offers insurance through a dedicated network of more than 4,200 agents in over 30 states.

National Lloyds Nevada Marketing and Sales Rep. Justin Lloyd (right) at an agent appreciation event.

Taking the Lead with Tech Enhancements For National Lloyds Corporation, providing simple and innovative technology solutions is not just a business goal—it’s critical to the success of the company’s distribution model.

Insurance agents and customers alike demand systems that are easy to navigate and use.

That’s why the company has invested over two years in implementing a new core processing platform that provides an enhanced experience for its users.

“Over the last six months, we’ve hit major milestones with our core system upgrade, rolling out improved tools for our new and

existing clients,” said Mitch Jawitz, National Lloyds Corporation vice president of marketing and sales. “We’re excited about what the new platform offers our users: new electronic payment options, more flexible down payment options, better underwriting tools for our agents, and improved output for both customers and agents. Recent changes to the new system have improved the time is takes for an agent to perform a quote from six minutes to an industryleading one minute.”

In several states, new National Lloyds clients are now onboarded into the new system, and

existing clients are being migrated in a phased approach to minimize disruption. Customers in the Arizona market have already moved to the solution and the migration of Tennessee clients is underway. The Texas market is on target for migration in early 2017.

“We’ve made great progress, but we have more work to do,” added Jawitz. “We’ll continue to further improve our solutions as we strive for perfection.”

A Winning Team NFL legend Emmitt Smith and wife Pat shine in PlainsCapital Bank customer ad campaign

© 2016 Hilltop Holdings Inc. Product of the Marketing & Communications Department

12

PrimeLending

PrimeLending associates are continually recognized for their leadership and performance.

A Clear Direction for the New Year

Earning Our Customers’ Trust For Hilltop Holdings, 2016 was another exciting and productive year. After completing 36 months of

strategic mergers and acquisitions, we spent the latter half of this year reorganizing and simplifying our organizational structure to improve productivity and collaboration among our family of companies. We end the year stronger and better-positioned to achieve our goal to build a premier, diversified financial services firm.

The industry recognition and positive feedback we received in 2016 are reflective of our ongoing financial strength and stability and our employees’ continued commitment to exceeding our customers’ expectations.

In 2017, we will remain intently focused on the things that matter most: providing the best service around; offering comprehensive financial solutions to meet all our customers’ needs; investing in the communities we serve; and doing our part to help our local economies grow.

As we embark upon another year, we are thankful for our dedicated employees and for the opportunity to build and deepen relationships with our customers. We look forward to 2017 and the potential it holds for us all. We wish you a joyous and prosperous New Year!

Jeremy B. Ford Co-CEO and President

Alan B. White Co-CEO and Vice Chairman

Building a supportive, professional environment is key to company culture.

PrimeLending celebrating 30 amazing years of growth and success.

Fortune and Fame In Fortune’s 2016 “100 Best Workplaces for Women,” PrimeLending ranks No. 5 and is one of only four mortgage firms highlighted for setting the standard for work-life practices in the U.S. In 2015, PrimeLending was recognized on the magazine’s inaugural list of the 100 Best Workplaces for Women, ranking No. 65.

“A diverse and inclusive workplace is not only good for our company and our clients, but it is also a source of competitive strength,” said Todd Salmans, CEO of PrimeLending. “It makes us a stronger firm that can attract and retain top talent at all levels to better serve the needs of our customers, our people and our community. It’s a privilege to be honored once again in this manner.”

The ranking is the result of an anonymous survey conducted by Great Places to Work of more than 137,000 women across numerous companies and industries. The ranking is based on employee assessments of a range of issues from communication with management, options for development and training, fairness of promotions, and level of support for employees’

personal lives, among other factors.

The ranking also examined how wellrepresented women are within the general workforce and management and executive positions.

At PrimeLending, leadership consists of 57% women, in relation to the entirety of the organization which is 62% female. PrimeLending employs more than 2,800 people nationally.

Michael Bush, CEO of Great Places to Work, Fortune’s longtime research partner in developing the magazine’s highly regarded annual business rankings, said companies on the list are leaders at creating environments that support equitable pay practices, provide female employees with more training opportunities, and foster a more inclusive environment with management regarding decisions directly affecting women in the workplace.

PrimeLending earned additional recognition from Fortune magazine in 2016, including being named No. 2 for “Best Workplaces in Finance and Insurance” and No. 9 for "Best Workplaces for Gen X’ers.”

11

FORTUNE 100 BEST WORKPLACES FOR WOMEN

FORTUNE BEST WORKPLACES IN FINANCE AND INSURANCE

FORTUNE BEST WORKPLACES FOR GEN X'ERS

NO.

5

NO.

2

NO.

9

Hilltop Holdings

PrimeLending

North to Alaska On October 24, 2016, PrimeLending proudly celebrated the opening of its first office in Alaska. With the addition of the new Anchorage location, the Dallas-based residential mortgage originator now has retail branches in 42 states.

“We’re excited to be expanding our presence in the Pacific Northwest,” said Scott Bristol, president of PrimeLending. “As the state’s largest city, Anchorage offers an ideal point of entrance for us into the market. We look forward to introducing Alaska’s homeowners to our superior line of mortgage products and our awardwinning customer service culture.”

Located at 3800 Centerpoint Drive, Ste. 920, in Anchorage, the branch is

‘anchored’ by a team of eight home loan professionals with a combined 95 years of mortgage industry experience in the Anchorage and greater Alaska market.

“We’re very excited to announce the opening of our flagship Alaska branch,” said PrimeLending Branch Manager Leonard Cullip. “With the level of expertise and leadership of this initial Anchorage team, along with the national strength and quality of PrimeLending, Alaskans now have a level of customer service that we believe our customers deserve.”

Founded in 1986, PrimeLending is one of the top 10 mortgage lenders in the nation based on purchase units.

Helping Homelessness PrimeLending’s new Anchorage, Alaska branch opened Oct. 24.

The Cottages at Hickory Crossing (pictured below) provide housing for Dallas' homeless.

In September, the City of Dallas unveiled its first major supportive housing project built specifically for the homeless – a project of which Dallas-based PrimeLending is a proud sponsor. Part of a public-private initiative to help get the city’s most chronically homeless off the street, The Cottages at Hickory Crossing is a community of 50 400-square-foot houses nestled just south of downtown on a parcel of land that was formerly home to a tent city.

PrimeLending volunteers worked with representatives of CitySquare, a human services charity dedicated to fighting poverty in Dallas, to help get the cottages move-in ready.

“Our employee-driven volunteer committee does a tremendous job of identifying community projects and organizations for the company

10

National Recognition In 2016, Hilltop Holdings was honored to be ranked among some of the top companies in the nation by notable magazines including Forbes, Fortune, and Bank Director.

Most recently, Hilltop was named to Fortune’s 2016 list of 100 Fastest-Growing Companies, coming in 31st in the U.S. Published in August, Bank Director magazine’s 2016 Bank Performance Scorecard ranked Hilltop as the second highest performing bank nationally among midsized banks between $5 billion and $50 billion in assets. Hilltop Holdings earned the No. 1 spot for best performing midsize

FORBES BEST BANKS IN AMERICA

NO.

5

banks in the state of Texas.

“These rankings are a testament to Hilltop’s financial strength and stability,” said Jeremy B. Ford, Hilltop Holdings co-CEO and president.

“We are very proud to be recognized among some of the most prominent companies in the world.”

Earlier in the year, Hilltop ranked No. 5 nationally on Forbes’ best banks listing of the Top 100 largest publicly traded banks and thrifts. Hilltop’s ranking increased over the previous year, where it was listed at 18th.

FORTUNE 100 FASTEST GROWING COMPANIES

NO.

31

“There is a common set of values woven into the way we do business – values that empower us toward the future with strength and momentum,” said Alan B. White, Hilltop Holdings co-CEO and vice chairman. “When you stick to your principles and focus on your customers, the recognition will come.”

At Hilltop Holdings, we believe that working with integrity, building strong relationships with our customers, and giving back to our communities all directly contribute to our growth and accomplishments. We’re proud to be recognized for our efforts.

BANK DIRECTOR 2016 BANK PERFORMANCE SCORECARD

to support,” said Todd Salmans, PrimeLending CEO. “We understand the impact homeownership has on people’s lives – all people – and we immediately knew that we wanted to be part of this project.”

Residents were identified based on their emotional and physical needs and the extent of their chronic homelessness. The community also provides on-site access to mental and physical healthcare services for residents, as well as job skills training.

“The challenge of homelessness is an ongoing battle, however this community is a structural symbol of what is possible, one cottage at a time,” said Salmans. “We believe a home can be the foundation of a better life, and we wish all the best to the new residents of The Cottages at Hickory Crossing.”

A specially designed tour bus generates excitement for the new Hilltop organizational roll-out.

Hilltop Holdings Co-CEO and President Jeremy B. Ford talks to employees about Hilltop's future.

3

NO.

2

HilltopSecurities

PlainsCapital Bank

Dallas Market Expansion The booming North Texas economy provides continued growth opportunities for PlainsCapital Bank.

In 2016, PlainsCapital expanded its footprint in the Dallas market, unveiling a new location in the Baylor Medical District near downtown and announcing the addition of a new Frisco location next year.

The opening of the Baylor branch on Nov. 14, 2016, marked PlainsCapital’s first location east of Interstate 75 (a major north-south thoroughfare), enabling the Bank to better serve the eastern side of the metroplex, while at the same time investing in the underserved area around Baylor hospital. Additionally, the location will support PlainsCapital’s healthcare initiative in response to North Texas’ rapidly growing healthcare market.

The new PlainsCapital Bank Baylor branch located in Dallas’ Baylor medical district.

The regional economic boom continues to push the Dallas metroplex further north to accommodate growing population and business needs. Frisco and the

surrounding northern communities lie at the heart of the whirlwind of growth and development. This past fall, PlainsCapital announced that it would be increasing its Frisco operations, opening a new location to better serve the expanding needs of its commercial and individual customers. The branch will be located in The Star – the brand new headquarters for the Dallas Cowboys.

“PlainsCapital’s success and growth in the Dallas market is founded on the strong relationships our bankers have built with our customers,” said PlainsCapital Bank Dallas Region Chairman George McCleskey. “The same holds true as we continue building our presence in the market.

We look forward to helping our current and future customers grow their businesses and exceed their financial goals.”

In 2017, PlainsCapital’s North Texas footprint will grow to 22 branches.

Junior Achievement Day This past October, PlainsCapital Bank employees in Dallas took a break from their regular jobs and transformed into elementary school teachers for the day. As part of the Junior Achievement program, the group of Bank volunteers spent the day at Oran Roberts Elementary School teaching 290 third, fourth and fifth grade students in 14 classrooms about financial literacy.

The curriculum addresses personal finance, entrepreneurship, business management, and the components that make up a community.

The topics were reinforced with fun classroom exercises, creative projects, and interactive group activities and games.

“Through the Junior Achievement program, we are able to help young students with financial literacy concepts that may not be brought up at home,” said Brent Raindl, PlainsCapital Bank Dallas market president. “It’s an opportunity to engage with kids about how these financial concepts relate to them, their families, neighbors, and their community, in a manner that is easy for them understand. Even

4

at a young age, they can begin to realize the world is bigger than me, my home, my block.”

Raindl added, “I think Junior Achievement is a tremendous program. I believe it fills an important need in the community, and I look forward to going out to the school each year.”

PlainsCapital Bank has partnered with Junior Achievement Dallas for several years, providing volunteer classroom support for Oran Roberts Elementary, which is located in one of the city’s more economically challenged neighborhoods.

Clearing on the Rise Investment News magazine’s recently published 2016 Custodians and Clearing Firms ranking named Dallasbased HilltopSecurities the third largest clearing firm in the nation, serving 178 correspondent firms. The ranking is an annual assessment of the largest U.S. clearing firms based on number of broker-dealer clients.

This is HilltopSecurities' initial ranking

by Investment News since Southwest Securities and FirstSouthwest merged

INVESTMENT NEWS' LARGEST CUSTODIANS AND CLEARING FIRMS

to form the company in 2015, and the ranking cites HilltopSecurities' 31.9 percent increase over last year’s position.

“The merger of our two legacy firms instantly increased the scale of our clearing business, and we are wellpositioned to continue to grow both in terms of new business and organic expansion,” said HilltopSecurities Head of Clearing Lana Calton.

NO.

3

HilltopSecurities’ clearing services (above) and financial advisory services (below) continue to set industry standards.

Improving Transparency A critical element of financial services is transparency – with clients, employees and strategic partners.

With that in mind, HilltopSecurties’ Wealth Management division developed an informative video for its network of financial advisors promoting the firm’s Certainty Circle of Life (CCOL) business philosophy to aid in the company’s mission for improved client transparency.

CCOL was created to help financial advisors and their clients engage in a series of conversations that focus on the client’s life goals and the appropriate alignment of their investments relative to those goals.

The video outlines how CCOL works hand-in-hand with MoneyGuide Pro® (MGP), Wealth Management’s

financial planning software. MGP is an interactive tool that involves clients in the information-gathering process and assists the advisor in pinpointing a client’s stage-of-life in order to recommend appropriate investments and products.

“The message underscored throughout CCOL is helping our clients continue to make better decisions regarding their finances,” said Jurgen Simons, HilltopSecurities Vice President of Business Development for Wealth Management. "It’s essential that we help our clients understand the importance of working with our financial advisors to help them navigate through their financial goals as their lives unfold.”

9

PlainsCapital Bank

HilltopSecurities

25 Years of Leadership In 1991, when Hill Feinberg joined HilltopSecurities (then FirstSouthwest), George H. W. Bush was in the Oval Office, the Soviet Union had collapsed, the Gulf War was wrapping up, and the movie " The Silence of the Lambs" was the Academy Award contender for Best Picture. Twenty-five years later, Feinberg still leads the investment banking and brokerage services firm that serves some of the nation’s largest individual and institutional investors, broker-dealers, government entities and financial intermediaries.

Hilltop Holdings celebrated Feinberg’s 25th anniversary as chairman and CEO of HilltopSecurities, hosting a luncheon in his honor, followed by an employee celebration held at HilltopSecurities’ Dallas headquarters.

Hill Feinberg celebrates 25 years as chairman and CEO of HilltopSecurities.

Hilltop Holdings Co-CEO and Vice Chairman Alan B. White (below left) joined in honoring Feinberg's accomplishments.

“HilltopSecurities’ success, including that of FirstSouthwest, is due in large part to Hill’s tremendous leadership skills,” said Hilltop Holdings co-CEO and Vice Chairman Alan B. White, who attended the celebration. “I’ve known Hill for 20 years. He is committed to building for the long term, and he provides a steadiness that clients and employees have come to depend on.”

It’s been quite a journey for Feinberg, who grew up in Columbus, Georgia.

He joined the United States Army Corps of Engineers in 1969, fresh out of the University of Georgia, and was a 1st Lieutenant in Vietnam. After honorably serving his country, he entered the private sector and began building the foundation of what would become a 45-year career in the financial services sector. A longtime Dallas investment banker, Feinberg held senior management positions at Bear Stearns & Co. and Salomon

8

Brothers, respectively, prior to joining FirstSouthwest.

Reflecting on his career Feinberg said, “One of the things I’ve learned is that I've never learned enough." Still, he believes firmly that there is always a right choice to be made in business, and the most successful people are those who work hard at taking care of employees and clients.

From 1996 to 2004, Feinberg led FirstSouthwest in a series of national acquisitions that expanded the firm’s investment banking services, and he navigated the company’s strategic merger with PlainsCapital Corporation in 2008. He has participated in dozens of prominent industry panels over the years and is a sought-after speaker on matters related to municipal securities and policies. Feinberg served on the Municipal Securities Rulemaking Board (MSRB) Board of Directors from 2000 to 2003 and was chairman of the board during the final year of his term.

He also has devoted much of his time to community work, generously supporting charities, hospitals and academic institutions. He currently serves as chairman of the board for Phoenix House of Texas and is a member of the Baylor Healthcare System Foundation Board of Directors, as well as the St. Marks School of Texas Board of Trustees.

A member of the University of Georgia Terry School of Business Dean’s Advisory Council, Feinberg was recognized by the university in 2008 with the Terry School of Business’ Distinguished Alumni Award.

Ad Campaign Packs Celebrity Punch PlainsCapital kicked off the third phase of its Swagger ad campaign this fall, featuring celebrity PlainsCapital customers proudly stating “My Bank’s Got Swagger.” Celebrities showcased in the ads included prominent business magnate T. Boone Pickens; investor, TV personality and Dallas Mavericks owner Mark Cuban; and NFL Hall-of-Famer, entrepreneur and philanthropist Emmitt Smith and his equally talented and involved wife, Pat. The Swagger campaign, which debuted last spring, included billboard, newspaper and magazine ads, as well as web-based and social media marketing components. Additionally, a television ad was created specifically for the Lubbock market.

Developed in-house, the initial idea for the ad campaign came from Hilltop Holdings co-CEO and PlainsCapital Bank Chairman Alan B. White. The creative work began with the PlainsCapital marketing team developing a purpose statement around the Bank’s values and core customers.

“Building on Alan’s idea, the Swagger campaign was designed to emphasize the trust PlainsCapital bankers have earned from their customers, and the confidence that creates in our organization,” said Hilltop Holdings Senior Vice President and Marketing Manager Jennifer Sterns.

venue to launch the campaign, debuting the “We’ve Got Swagger” ads at the 2016 Dean & Deluca Colonial Invitational Golf Tournament in Fort Worth before rolling out the campaign statewide. Phase two delved further into the Swagger narrative, launching over the summer and spotlighting bankers in each of PlainsCapital’s markets who have “Confidence You Can Bank On.” "The Swagger campaign provided a unique opportunity to showcase some of the talented bankers and loyal customers who have helped make PlainsCapital one of the leading banks in Texas," said Sterns.

As a means to begin communicating that message, PlainsCapital selected a high-profile

The Swagger campaign was designed to emphasize the trust PlainsCapital bankers have earned from their customers.

My Bank’s Got

SWAGGER PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of Mark Cuban, renowned investor, businessman and owner of the Dallas Mavericks. Are you ready for a bank with swagger?

214.525.9100 PlainsCapital.com

We’ve Got SWAGGER 2016 PlainsCapital Bank

Equal Housing Lender Member FDIC

My Bank’s Got

Our Bank’s Got

SWAGGER

SWAGGER PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of the legendary football icon, businessman, and enterpreneur Emmitt Smith and his wife Pat, the unstoppable philanthropist.

Are you ready for a bank with swagger?

PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of visionary business leader and innovative philanthropist T. Boone Pickens. Are you ready for a bank with swagger?

214.525.9100

PlainsCapital.com

214.525.9100

We’ve Got SWAGGER

We’ve Got SWAGGER

2016 PlainsCapital Bank

PlainsCapital.com

2016 PlainsCapital Bank

Equal Housing Lender Member FDIC

5

Equal Housing Lender Member FDIC

Hilltop From Coast to Coast

San Francisco, CA As part of the 9/11 National Day of Service and Remembrance, members of the San Francisco Wealth Management office participated in the 5K San Francisco Giant Race, raising $1,400 for the local charity Project Open Hand.

Dallas, TX

Boston, MA Chief Administrative Officer John Muschalek, Compliance Administrator and breast cancer survivor Angela Irvine and President and COO Bob Peterson show support for breast cancer awareness as part of HilltopSecurities' inaugural Pink and Jeans Campaign.

Waco, TX

HilltopSecurities Director and Investment Banker Susan Kendall completed her seventh Boston Marathon Jimmy Fund Walk in September benefitting the Dana Farber Cancer Institute. Kendall has raised nearly $30,000 for cancer research in the Boston area.

Baton Rouge, LA

Palm Beach, FL In August, 19 employees of PrimeLending in the Baton Rouge area felt the impact of the catastrophic rainfall that flooded much of the South. PrimeLending team members raised $50,000 to help those employees get back on their feet.

National Lloyds partnered with the Dr. Pepper Museum and Free Enterprise Institute to underwrite a mobile outreach education program for Waco-area elementary schools.

In response to Hurricane Matthew, HilltopSecurities Managing Director Jason Lisec organized a relief effort that raised more than 10,000 pounds of supplies for residents of the Bahamas.

Austin, TX All across the U.S., Hilltop Holdings employees are making a difference in their communities. From raising money and awareness for charities to supporting educational initiatives and disaster relief efforts, our employees are raising the bar for giving back  and making us proud.

McAllen, TX PlainsCapital Bank PrimeLending Employees from the PlainsCapital Bank and PrimeLending offices joined together to support the local community of Cedar Park in Austin. PlainsCapital Bank employees Erin Johnson and Mark Miralles and PrimeLending employee Mary Kennedy painted the Bank’s logo onto the Ice at Cedar Park’s H-E-B Center.

McAllen Bank employees helped students shop for school supplies as part of United Way of South Texas’ 2016 Back-To-School “In Style”Shopping Spree at Target.

HilltopSecurities National Lloyds

Hilltop From Coast to Coast

San Francisco, CA As part of the 9/11 National Day of Service and Remembrance, members of the San Francisco Wealth Management office participated in the 5K San Francisco Giant Race, raising $1,400 for the local charity Project Open Hand.

Dallas, TX

Boston, MA Chief Administrative Officer John Muschalek, Compliance Administrator and breast cancer survivor Angela Irvine and President and COO Bob Peterson show support for breast cancer awareness as part of HilltopSecurities' inaugural Pink and Jeans Campaign.

Waco, TX

HilltopSecurities Director and Investment Banker Susan Kendall completed her seventh Boston Marathon Jimmy Fund Walk in September benefitting the Dana Farber Cancer Institute. Kendall has raised nearly $30,000 for cancer research in the Boston area.

Baton Rouge, LA

Palm Beach, FL In August, 19 employees of PrimeLending in the Baton Rouge area felt the impact of the catastrophic rainfall that flooded much of the South. PrimeLending team members raised $50,000 to help those employees get back on their feet.

National Lloyds partnered with the Dr. Pepper Museum and Free Enterprise Institute to underwrite a mobile outreach education program for Waco-area elementary schools.

In response to Hurricane Matthew, HilltopSecurities Managing Director Jason Lisec organized a relief effort that raised more than 10,000 pounds of supplies for residents of the Bahamas.

Austin, TX All across the U.S., Hilltop Holdings employees are making a difference in their communities. From raising money and awareness for charities to supporting educational initiatives and disaster relief efforts, our employees are raising the bar for giving back  and making us proud.

McAllen, TX PlainsCapital Bank PrimeLending Employees from the PlainsCapital Bank and PrimeLending offices joined together to support the local community of Cedar Park in Austin. PlainsCapital Bank employees Erin Johnson and Mark Miralles and PrimeLending employee Mary Kennedy painted the Bank’s logo onto the Ice at Cedar Park’s H-E-B Center.

McAllen Bank employees helped students shop for school supplies as part of United Way of South Texas’ 2016 Back-To-School “In Style”Shopping Spree at Target.

HilltopSecurities National Lloyds

PlainsCapital Bank

HilltopSecurities

25 Years of Leadership In 1991, when Hill Feinberg joined HilltopSecurities (then FirstSouthwest), George H. W. Bush was in the Oval Office, the Soviet Union had collapsed, the Gulf War was wrapping up, and the movie " The Silence of the Lambs" was the Academy Award contender for Best Picture. Twenty-five years later, Feinberg still leads the investment banking and brokerage services firm that serves some of the nation’s largest individual and institutional investors, broker-dealers, government entities and financial intermediaries.

Hilltop Holdings celebrated Feinberg’s 25th anniversary as chairman and CEO of HilltopSecurities, hosting a luncheon in his honor, followed by an employee celebration held at HilltopSecurities’ Dallas headquarters.

Hill Feinberg celebrates 25 years as chairman and CEO of HilltopSecurities.

Hilltop Holdings Co-CEO and Vice Chairman Alan B. White (below left) joined in honoring Feinberg's accomplishments.

“HilltopSecurities’ success, including that of FirstSouthwest, is due in large part to Hill’s tremendous leadership skills,” said Hilltop Holdings co-CEO and Vice Chairman Alan B. White, who attended the celebration. “I’ve known Hill for 20 years. He is committed to building for the long term, and he provides a steadiness that clients and employees have come to depend on.”

It’s been quite a journey for Feinberg, who grew up in Columbus, Georgia.

He joined the United States Army Corps of Engineers in 1969, fresh out of the University of Georgia, and was a 1st Lieutenant in Vietnam. After honorably serving his country, he entered the private sector and began building the foundation of what would become a 45-year career in the financial services sector. A longtime Dallas investment banker, Feinberg held senior management positions at Bear Stearns & Co. and Salomon

8

Brothers, respectively, prior to joining FirstSouthwest.

Reflecting on his career Feinberg said, “One of the things I’ve learned is that I've never learned enough." Still, he believes firmly that there is always a right choice to be made in business, and the most successful people are those who work hard at taking care of employees and clients.

From 1996 to 2004, Feinberg led FirstSouthwest in a series of national acquisitions that expanded the firm’s investment banking services, and he navigated the company’s strategic merger with PlainsCapital Corporation in 2008. He has participated in dozens of prominent industry panels over the years and is a sought-after speaker on matters related to municipal securities and policies. Feinberg served on the Municipal Securities Rulemaking Board (MSRB) Board of Directors from 2000 to 2003 and was chairman of the board during the final year of his term.

He also has devoted much of his time to community work, generously supporting charities, hospitals and academic institutions. He currently serves as chairman of the board for Phoenix House of Texas and is a member of the Baylor Healthcare System Foundation Board of Directors, as well as the St. Marks School of Texas Board of Trustees.

A member of the University of Georgia Terry School of Business Dean’s Advisory Council, Feinberg was recognized by the university in 2008 with the Terry School of Business’ Distinguished Alumni Award.

Ad Campaign Packs Celebrity Punch PlainsCapital kicked off the third phase of its Swagger ad campaign this fall, featuring celebrity PlainsCapital customers proudly stating “My Bank’s Got Swagger.” Celebrities showcased in the ads included prominent business magnate T. Boone Pickens; investor, TV personality and Dallas Mavericks owner Mark Cuban; and NFL Hall-of-Famer, entrepreneur and philanthropist Emmitt Smith and his equally talented and involved wife, Pat. The Swagger campaign, which debuted last spring, included billboard, newspaper and magazine ads, as well as web-based and social media marketing components. Additionally, a television ad was created specifically for the Lubbock market.

Developed in-house, the initial idea for the ad campaign came from Hilltop Holdings co-CEO and PlainsCapital Bank Chairman Alan B. White. The creative work began with the PlainsCapital marketing team developing a purpose statement around the Bank’s values and core customers.

“Building on Alan’s idea, the Swagger campaign was designed to emphasize the trust PlainsCapital bankers have earned from their customers, and the confidence that creates in our organization,” said Hilltop Holdings Senior Vice President and Marketing Manager Jennifer Sterns.

venue to launch the campaign, debuting the “We’ve Got Swagger” ads at the 2016 Dean & Deluca Colonial Invitational Golf Tournament in Fort Worth before rolling out the campaign statewide. Phase two delved further into the Swagger narrative, launching over the summer and spotlighting bankers in each of PlainsCapital’s markets who have “Confidence You Can Bank On.” "The Swagger campaign provided a unique opportunity to showcase some of the talented bankers and loyal customers who have helped make PlainsCapital one of the leading banks in Texas," said Sterns.

As a means to begin communicating that message, PlainsCapital selected a high-profile

The Swagger campaign was designed to emphasize the trust PlainsCapital bankers have earned from their customers.

My Bank’s Got

SWAGGER PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of Mark Cuban, renowned investor, businessman and owner of the Dallas Mavericks. Are you ready for a bank with swagger?

214.525.9100 PlainsCapital.com

We’ve Got SWAGGER 2016 PlainsCapital Bank

Equal Housing Lender Member FDIC

My Bank’s Got

Our Bank’s Got

SWAGGER

SWAGGER PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of the legendary football icon, businessman, and enterpreneur Emmitt Smith and his wife Pat, the unstoppable philanthropist.

Are you ready for a bank with swagger?

PlainsCapital has the swagger to give you a different – and better – Texas banking experience. Our bankers are determined to earn your business and help you achieve your financial goals.

That’s how we earned the trust of visionary business leader and innovative philanthropist T. Boone Pickens. Are you ready for a bank with swagger?

214.525.9100

PlainsCapital.com

214.525.9100

We’ve Got SWAGGER

We’ve Got SWAGGER

2016 PlainsCapital Bank

PlainsCapital.com

2016 PlainsCapital Bank

Equal Housing Lender Member FDIC

5

Equal Housing Lender Member FDIC

HilltopSecurities

PlainsCapital Bank

Dallas Market Expansion The booming North Texas economy provides continued growth opportunities for PlainsCapital Bank.

In 2016, PlainsCapital expanded its footprint in the Dallas market, unveiling a new location in the Baylor Medical District near downtown and announcing the addition of a new Frisco location next year.

The opening of the Baylor branch on Nov. 14, 2016, marked PlainsCapital’s first location east of Interstate 75 (a major north-south thoroughfare), enabling the Bank to better serve the eastern side of the metroplex, while at the same time investing in the underserved area around Baylor hospital. Additionally, the location will support PlainsCapital’s healthcare initiative in response to North Texas’ rapidly growing healthcare market.

The new PlainsCapital Bank Baylor branch located in Dallas’ Baylor medical district.

The regional economic boom continues to push the Dallas metroplex further north to accommodate growing population and business needs. Frisco and the

surrounding northern communities lie at the heart of the whirlwind of growth and development. This past fall, PlainsCapital announced that it would be increasing its Frisco operations, opening a new location to better serve the expanding needs of its commercial and individual customers. The branch will be located in The Star – the brand new headquarters for the Dallas Cowboys.

“PlainsCapital’s success and growth in the Dallas market is founded on the strong relationships our bankers have built with our customers,” said PlainsCapital Bank Dallas Region Chairman George McCleskey. “The same holds true as we continue building our presence in the market.

We look forward to helping our current and future customers grow their businesses and exceed their financial goals.”

In 2017, PlainsCapital’s North Texas footprint will grow to 22 branches.

Junior Achievement Day This past October, PlainsCapital Bank employees in Dallas took a break from their regular jobs and transformed into elementary school teachers for the day. As part of the Junior Achievement program, the group of Bank volunteers spent the day at Oran Roberts Elementary School teaching 290 third, fourth and fifth grade students in 14 classrooms about financial literacy.

The curriculum addresses personal finance, entrepreneurship, business management, and the components that make up a community.

The topics were reinforced with fun classroom exercises, creative projects, and interactive group activities and games.

“Through the Junior Achievement program, we are able to help young students with financial literacy concepts that may not be brought up at home,” said Brent Raindl, PlainsCapital Bank Dallas market president. “It’s an opportunity to engage with kids about how these financial concepts relate to them, their families, neighbors, and their community, in a manner that is easy for them understand. Even

4

at a young age, they can begin to realize the world is bigger than me, my home, my block.”

Raindl added, “I think Junior Achievement is a tremendous program. I believe it fills an important need in the community, and I look forward to going out to the school each year.”

PlainsCapital Bank has partnered with Junior Achievement Dallas for several years, providing volunteer classroom support for Oran Roberts Elementary, which is located in one of the city’s more economically challenged neighborhoods.

Clearing on the Rise Investment News magazine’s recently published 2016 Custodians and Clearing Firms ranking named Dallasbased HilltopSecurities the third largest clearing firm in the nation, serving 178 correspondent firms. The ranking is an annual assessment of the largest U.S. clearing firms based on number of broker-dealer clients.

This is HilltopSecurities' initial ranking

by Investment News since Southwest Securities and FirstSouthwest merged

INVESTMENT NEWS' LARGEST CUSTODIANS AND CLEARING FIRMS

to form the company in 2015, and the ranking cites HilltopSecurities' 31.9 percent increase over last year’s position.

“The merger of our two legacy firms instantly increased the scale of our clearing business, and we are wellpositioned to continue to grow both in terms of new business and organic expansion,” said HilltopSecurities Head of Clearing Lana Calton.

NO.

3

HilltopSecurities’ clearing services (above) and financial advisory services (below) continue to set industry standards.

Improving Transparency A critical element of financial services is transparency – with clients, employees and strategic partners.

With that in mind, HilltopSecurties’ Wealth Management division developed an informative video for its network of financial advisors promoting the firm’s Certainty Circle of Life (CCOL) business philosophy to aid in the company’s mission for improved client transparency.

CCOL was created to help financial advisors and their clients engage in a series of conversations that focus on the client’s life goals and the appropriate alignment of their investments relative to those goals.

The video outlines how CCOL works hand-in-hand with MoneyGuide Pro® (MGP), Wealth Management’s

financial planning software. MGP is an interactive tool that involves clients in the information-gathering process and assists the advisor in pinpointing a client’s stage-of-life in order to recommend appropriate investments and products.

“The message underscored throughout CCOL is helping our clients continue to make better decisions regarding their finances,” said Jurgen Simons, HilltopSecurities Vice President of Business Development for Wealth Management. "It’s essential that we help our clients understand the importance of working with our financial advisors to help them navigate through their financial goals as their lives unfold.”

9

Hilltop Holdings

PrimeLending

North to Alaska On October 24, 2016, PrimeLending proudly celebrated the opening of its first office in Alaska. With the addition of the new Anchorage location, the Dallas-based residential mortgage originator now has retail branches in 42 states.

“We’re excited to be expanding our presence in the Pacific Northwest,” said Scott Bristol, president of PrimeLending. “As the state’s largest city, Anchorage offers an ideal point of entrance for us into the market. We look forward to introducing Alaska’s homeowners to our superior line of mortgage products and our awardwinning customer service culture.”

Located at 3800 Centerpoint Drive, Ste. 920, in Anchorage, the branch is

‘anchored’ by a team of eight home loan professionals with a combined 95 years of mortgage industry experience in the Anchorage and greater Alaska market.

“We’re very excited to announce the opening of our flagship Alaska branch,” said PrimeLending Branch Manager Leonard Cullip. “With the level of expertise and leadership of this initial Anchorage team, along with the national strength and quality of PrimeLending, Alaskans now have a level of customer service that we believe our customers deserve.”

Founded in 1986, PrimeLending is one of the top 10 mortgage lenders in the nation based on purchase units.

Helping Homelessness PrimeLending’s new Anchorage, Alaska branch opened Oct. 24.

The Cottages at Hickory Crossing (pictured below) provide housing for Dallas' homeless.

In September, the City of Dallas unveiled its first major supportive housing project built specifically for the homeless – a project of which Dallas-based PrimeLending is a proud sponsor. Part of a public-private initiative to help get the city’s most chronically homeless off the street, The Cottages at Hickory Crossing is a community of 50 400-square-foot houses nestled just south of downtown on a parcel of land that was formerly home to a tent city.

PrimeLending volunteers worked with representatives of CitySquare, a human services charity dedicated to fighting poverty in Dallas, to help get the cottages move-in ready.

“Our employee-driven volunteer committee does a tremendous job of identifying community projects and organizations for the company

10

National Recognition In 2016, Hilltop Holdings was honored to be ranked among some of the top companies in the nation by notable magazines including Forbes, Fortune, and Bank Director.

Most recently, Hilltop was named to Fortune’s 2016 list of 100 Fastest-Growing Companies, coming in 31st in the U.S. Published in August, Bank Director magazine’s 2016 Bank Performance Scorecard ranked Hilltop as the second highest performing bank nationally among midsized banks between $5 billion and $50 billion in assets. Hilltop Holdings earned the No. 1 spot for best performing midsize

FORBES BEST BANKS IN AMERICA

NO.

5

banks in the state of Texas.

“These rankings are a testament to Hilltop’s financial strength and stability,” said Jeremy B. Ford, Hilltop Holdings co-CEO and president.

“We are very proud to be recognized among some of the most prominent companies in the world.”

Earlier in the year, Hilltop ranked No. 5 nationally on Forbes’ best banks listing of the Top 100 largest publicly traded banks and thrifts. Hilltop’s ranking increased over the previous year, where it was listed at 18th.

FORTUNE 100 FASTEST GROWING COMPANIES

NO.

31

“There is a common set of values woven into the way we do business – values that empower us toward the future with strength and momentum,” said Alan B. White, Hilltop Holdings co-CEO and vice chairman. “When you stick to your principles and focus on your customers, the recognition will come.”

At Hilltop Holdings, we believe that working with integrity, building strong relationships with our customers, and giving back to our communities all directly contribute to our growth and accomplishments. We’re proud to be recognized for our efforts.

BANK DIRECTOR 2016 BANK PERFORMANCE SCORECARD

to support,” said Todd Salmans, PrimeLending CEO. “We understand the impact homeownership has on people’s lives – all people – and we immediately knew that we wanted to be part of this project.”

Residents were identified based on their emotional and physical needs and the extent of their chronic homelessness. The community also provides on-site access to mental and physical healthcare services for residents, as well as job skills training.

“The challenge of homelessness is an ongoing battle, however this community is a structural symbol of what is possible, one cottage at a time,” said Salmans. “We believe a home can be the foundation of a better life, and we wish all the best to the new residents of The Cottages at Hickory Crossing.”

A specially designed tour bus generates excitement for the new Hilltop organizational roll-out.

Hilltop Holdings Co-CEO and President Jeremy B. Ford talks to employees about Hilltop's future.

3

NO.

2

PrimeLending

PrimeLending associates are continually recognized for their leadership and performance.

A Clear Direction for the New Year

Earning Our Customers’ Trust For Hilltop Holdings, 2016 was another exciting and productive year. After completing 36 months of

strategic mergers and acquisitions, we spent the latter half of this year reorganizing and simplifying our organizational structure to improve productivity and collaboration among our family of companies. We end the year stronger and better-positioned to achieve our goal to build a premier, diversified financial services firm.

The industry recognition and positive feedback we received in 2016 are reflective of our ongoing financial strength and stability and our employees’ continued commitment to exceeding our customers’ expectations.

In 2017, we will remain intently focused on the things that matter most: providing the best service around; offering comprehensive financial solutions to meet all our customers’ needs; investing in the communities we serve; and doing our part to help our local economies grow.

As we embark upon another year, we are thankful for our dedicated employees and for the opportunity to build and deepen relationships with our customers. We look forward to 2017 and the potential it holds for us all. We wish you a joyous and prosperous New Year!

Jeremy B. Ford Co-CEO and President

Alan B. White Co-CEO and Vice Chairman

Building a supportive, professional environment is key to company culture.

PrimeLending celebrating 30 amazing years of growth and success.

Fortune and Fame In Fortune’s 2016 “100 Best Workplaces for Women,” PrimeLending ranks No. 5 and is one of only four mortgage firms highlighted for setting the standard for work-life practices in the U.S. In 2015, PrimeLending was recognized on the magazine’s inaugural list of the 100 Best Workplaces for Women, ranking No. 65.

“A diverse and inclusive workplace is not only good for our company and our clients, but it is also a source of competitive strength,” said Todd Salmans, CEO of PrimeLending. “It makes us a stronger firm that can attract and retain top talent at all levels to better serve the needs of our customers, our people and our community. It’s a privilege to be honored once again in this manner.”

The ranking is the result of an anonymous survey conducted by Great Places to Work of more than 137,000 women across numerous companies and industries. The ranking is based on employee assessments of a range of issues from communication with management, options for development and training, fairness of promotions, and level of support for employees’

personal lives, among other factors.

The ranking also examined how wellrepresented women are within the general workforce and management and executive positions.

At PrimeLending, leadership consists of 57% women, in relation to the entirety of the organization which is 62% female. PrimeLending employs more than 2,800 people nationally.

Michael Bush, CEO of Great Places to Work, Fortune’s longtime research partner in developing the magazine’s highly regarded annual business rankings, said companies on the list are leaders at creating environments that support equitable pay practices, provide female employees with more training opportunities, and foster a more inclusive environment with management regarding decisions directly affecting women in the workplace.

PrimeLending earned additional recognition from Fortune magazine in 2016, including being named No. 2 for “Best Workplaces in Finance and Insurance” and No. 9 for "Best Workplaces for Gen X’ers.”

11

FORTUNE 100 BEST WORKPLACES FOR WOMEN

FORTUNE BEST WORKPLACES IN FINANCE AND INSURANCE

FORTUNE BEST WORKPLACES FOR GEN X'ERS

NO.

5

NO.

2

NO.

9

4th Quarter 2016

National Lloyds

Nevada Growth Nevada is proving to be a potential high-growth market for National Lloyds Corporation. The Texas-based property and casualty insurance provider is expanding its physical presence in the state, which until recently has gone largely untapped.

“We believe Nevada offers growth opportunity for the company with less volatility, as the region has little catastrophe exposure,” said Bob Otis, National Lloyds Corporation CEO. To drive performance, National Lloyds added a Nevada marketing representative position over the summer and is in the process of increasing the number of agents and

offices in the state. The company is also planning product enhancements for 2017, which it anticipates will spur further growth in the region.

MOMENTUM A Hilltop Holdings Publication

Since 1948, National Lloyds Corporation has been working to make life easier for its customers, providing property and casualty insurance through its two underwriting companies: National Lloyds Insurance Company and American Summit Insurance Company. Headquartered in Waco, Texas, National Lloyds offers insurance through a dedicated network of more than 4,200 agents in over 30 states.

National Lloyds Nevada Marketing and Sales Rep. Justin Lloyd (right) at an agent appreciation event.

Taking the Lead with Tech Enhancements For National Lloyds Corporation, providing simple and innovative technology solutions is not just a business goal—it’s critical to the success of the company’s distribution model.

Insurance agents and customers alike demand systems that are easy to navigate and use.

That’s why the company has invested over two years in implementing a new core processing platform that provides an enhanced experience for its users.

“Over the last six months, we’ve hit major milestones with our core system upgrade, rolling out improved tools for our new and

existing clients,” said Mitch Jawitz, National Lloyds Corporation vice president of marketing and sales. “We’re excited about what the new platform offers our users: new electronic payment options, more flexible down payment options, better underwriting tools for our agents, and improved output for both customers and agents. Recent changes to the new system have improved the time is takes for an agent to perform a quote from six minutes to an industryleading one minute.”

In several states, new National Lloyds clients are now onboarded into the new system, and

existing clients are being migrated in a phased approach to minimize disruption. Customers in the Arizona market have already moved to the solution and the migration of Tennessee clients is underway. The Texas market is on target for migration in early 2017.

“We’ve made great progress, but we have more work to do,” added Jawitz. “We’ll continue to further improve our solutions as we strive for perfection.”

A Winning Team NFL legend Emmitt Smith and wife Pat shine in PlainsCapital Bank customer ad campaign

© 2016 Hilltop Holdings Inc. Product of the Marketing & Communications Department

12