Early Years

Company founders, Donald W. Webb and R. Dudley Webb grew up in the Appalachian coal mining town of Whitesburg in Letcher County, Kentucky. The Webb family, like many Eastern Kentucky families, has deep ties to the region going back many generations. The brothers’ grandfather, N.M. Webb, was not only an educator and postmaster in Whitesburg, but also a noted journalist, having founded what is today, one of the longest running newspapers in the United States, The Mountain Eagle in 1907. N.M. Webb and his wife Sarah Ellen had 10 children, 8 daughters and 2 sons. Woodford Webb was born in 1915 and went on to marry Elizabeth Combs in 1937. Together they raised their four children Donald, Dudley, Debby and Judy in a little house in Hot Spot owned by the Premium Coal Company where Woodford worked as an accountant. Country life in Eastern Kentucky was idyllic, filled with family, hard work and Appalachian traditions.

The Webb brothers soon left home upon their graduations from Whitesburg High School, but they never forgot their Kentucky roots. Starting with a small law practice, they would ultimately diversify and grow their business into one of the largest commercial real estate companies in the U.S., with developments from Washington DC to San Francisco and Boston to Key West. The Webb Companies to this day remains a family-run business headquartered in Lexington, Kentucky. The Webb family has owned N.M. Webb’s house located on Main Street in Whitesburg for 115 years where it will continue to be passed down to future generations as a memorial to the family’s Eastern Kentucky heritage.

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Family patriarch Woodford “Dood” Webb marries Elizabeth “Dottie” Combs in Whitesburg, Kentucky where they raise their four children, Donald, Dudley, Debby and Judy.


Donald Woodford Webb born.


Ralph Dudley Webb born.


The brothers grow up in Letcher County, Kentucky surrounded by a large extended family including second cousin Loretta Webb who grows up to become country singing legend Loretta Lynn.


Don Webb graduates from Whitesburg High School and leaves Eastern Kentucky to attend the Virginia Military Institute in Lexington, VA and then transfers and graduates from Georgetown College and the University of Kentucky College of Law in Lexington, KY.


Dudley Webb graduates from Whitesburg High School and follows in his brother’s footsteps by graduating from Georgetown College and the University of Kentucky College of Law.


Don Webb graduates from law school, marries Julie Howser in Frankfort, Kentucky, and begins his career, first in state government with the Kentucky Department of Economic Development, and then in Washington DC as legal advisor to the national Advisory Commission on Civil Disorders under President Lyndon Johnson. He relocates to Louisville, Kentucky to co-directed the Senate campaign of Katherine Peden and practice law with the firm of Handmaker, Weber & Meyer.


Donald W. Webb, Jr. is born to Don and Julie Webb and is referred to as “Woodford” after his grandfather.

Young Lawyers Start The Webb Companies

While his brother Don was enjoying a successful legal career with the firm of Handmaker, Weber and Meyer in Louisville, Dudley Webb opens his own law firm in Lexington upon his graduation from the University of Kentucky College of Law in 1968. Older brother Don soon joins him in Lexington, and together they form the law firm of Webb and Webb in 1971 with offices located in the Bank of Commerce Building. The law firm would evolve with various partners over the years including Charles Ward, Pat Sullivan, Time Cone and Jim Lemaster. Glenn A. Hoskins joins the firm in 1979 as a young associate and continues to work closely to this day with The Webb Companies on real estate projects as a partner in the firm now known as Webb, Hoskins, Brown and Thompson.

It is during this time, where Don and Dudley Webb begin working with Garvice Kincaid, the prominent Lexington businessman and financier. Through their association with Mr. Kincaid, the brothers learn the world of real estate investing and developing. They soon begin developing their own projects in Lexington and in 1972, they found The Webb Companies, a consolidation of real estate development, design, finance, legal, construction, marketing, leasing, brokerage, property management, and ancillary functions. Their early developments consist of industrial properties and duplexes, but they soon set their sights on larger projects. Their first major project, First Federal Plaza, breaks ground in 1975 on West Vine Street (current location of Old National Bank). Little did they know, this was just the beginning...

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Dudley Webb opens office for law practice.


Don Webb relocates to Lexington and together with Dudley opens the law firm of Webb and Webb with offices located in the Bank of Commerce Building on Main Street.


The Webb Companies is founded with offices located at Bank of Commerce Building.


Groundbreaking on the first major development project, First Federal Plaza located at 110 West Vine Street in downtown Lexington.


Glenn A. Hoskins joins the law firm Webb, Cone & Ward and begins a lifelong business association with the Webb brothers that continues to this day.


The Webb brothers, along with Dr. Ed Nighbert and thirty-eight Lexington physicians, found the Lexington Surgery Center, one of the nation’s early free-standing outpatient surgery centers. The Lexington Surgery Center ultimately becomes HealthSouth and is now traded on the NYSE as Encompass Health Corporation (EHC).

The Booming 80s

The next decade brings unprecedented growth to many U.S. cities. With the success of First Federal Plaza, Don and Dudley Webb turn their attention to revitalizing downtown Lexington into a destination for people to visit, work and live. In 1980, the NCAA declines Lexington’s bid to host one of the NCAA basketball tournament rounds due to the lack of hotel rooms. The Webb brothers, both lifelong University of Kentucky Wildcat basketball fans, announce they will develop a 300-room hotel to ensure Lexington is not overlooked again. They work to acquire a full city block located at the corner of Broadway and Vine Street, just steps from historic Rupp Arena. In 1982 they open the 368-room Radisson Plaza Hotel and the adjoining parking garage and 17-story office tower Vine Center. The hard work pays off and Lexington hosts the 1985 NCAA Final Four.

The Webb Companies continue to modernize Lexington, building over 5 million square feet of commercial real estate during the decade. Major projects include Corporate Center, Victorian Square, Festival Market, The Woodlands, Lexington Green, Regency Center, Melbourne Industrial Center and Tates Creek Shopping Center. The Lexington Financial Center, a 31 story gleaming office tower located in the heart of downtown Lexington, becomes their most visible project and defines the skyline of Lexington for future generations.

Don Webb, as Local Partner, manages all of the Lexington-based projects, as well as the day-to-day business affairs of The Webb Companies that grows to over 200 employees. Don is also an active civic leader, serving on many boards including the Kentucky Economic Development Corporation, the Kentucky Horse Park Commission, the Lexington Economic Development Commission, Commerce Lexington (Chairman), Good Samaritan Hospital, Triangle Foundation, Fund for the Arts, and First Security National Bank and Trust. He is also the primary founder of the Lexington Trolley Company and the Downtown Lexington Corporation.

Dudley Webb serves as the National Partner, traveling extensively to oversee The Webb Companies projects throughout the U.S. Major projects include Austin Center (Austin, TX), Dulles Corner (Arlington, VA), Durham Centre (Durham, NC), Le Chambord (New York, NY), Conch Harbor Marina (Key West, FL), BB&T Financial Center (Winston-Salem, NC), Gateway Plaza (Colorado Springs, CO), Settlers Green Outlet Mall (North Conway, NH), and Crescent Beach Condominiums (Marco Island, FL).

The Webb Companies, under Don and Dudley Webb’s leadership, grow to the 3rd largest diversified real estate development company in the country with projects valued at almost $1 Billion.

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Radisson Plaza Hotel and Vine Center open in downtown Lexington, Kentucky. The Webb Companies corporate offices move to the 17th floor of Vine Center.


Corporate Center suburban office park and The Woodlands luxury condominium complex break ground.


Don and Dudley Webb team with local prominent businessmen, Elmer Whitaker, W.T. Young, and Alex Campbell for the historic preservation of Victorian Square.


The Webb Companies is ranked the third largest diversified real estate development company in the U.S. by Building construction Design Magazine.


Major projects change the face of Lexington, including The Woodlands, Festival Market, Lexington Green, Tates Creek Center, Corporate Center, and Melbourne Industrial Center.


Construction of the Lexington Financial Center starts and is completed in 1987. The Webb Companies corporate headquarters occupy floors 30 and 31.


October 1, 1987, attorney Ronald C. Tritschler joins The Webb Companies after working with Dudley Webb on the Radisson Hotel project in his native Toledo, Ohio. He becomes one of the longest-tenured employees in the history of the company and currently serves as CEO and Senior Corporate Counsel.


Groundbreaking of Jamestown Marina in Lake Cumberland.


Dudley Webb invests in a local Petro Express convenience store with college friend, Paul Koshgerian. Together, along with friend and local businessman, Jay Hall, they grow the company to include over 40 Shell gas stations and convenience stores. The group sells the company in 2015 to Travelers Centers of America.

The 90s—A New Generation

The 1990s start with the grand opening of Palomar Center, a 200,000 square foot retail shopping center located on the south end of Lexington. After working hard to grow the business for the past two decades, new development slows in the 1990s and the Webb brothers focus on the management of the companies’ existing real estate holdings. Dudley Webb marries Marla Collins, daughter of Governor Martha Layne Collins and together raise their three children in Lexington. Don Webb’s son, Donald Woodford Webb, Jr., known as “Woodford” after his grandfather, works in every department of the company, learning the business from his father from the ground up. Woodford, a graduate of Washington & Lee University, earns his MBA from the University of Kentucky and JD degree from the Salmon P. Chase College of Law in 1996. After working as an Associate in the family law firm of Webb, Hoskins, Glover and Thompson for 3 years, Woodford is named President of The Webb Companies in 1999.

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Palomar Center Shopping Center opens.


Family patriarch, Woodford Webb, passes away at the age of 77 in Letcher County, Kentucky.


Donald Woodford Webb, Jr, known as “Woodford” after his grandfather, holds various positions in The Webb Companies from maintenance, to property management, to marketing and leasing.


Dudley Webb marries Marla Collins of Versailles, Kentucky.


Upon graduating from law school, Woodford Webb joins the firm Webb, Hoskins, Glover and Thompson as an Associate.


Woodford Webb is named President of The Webb Companies. His father, company co-founder, Don Webb semi-retires to Vero Beach, Florida.

The 2000s—CentrePointe

After 10 years away from The Webb Companies to focus on raising his children, Dudley Webb returns to real estate development in 2007 with an idea to build a mixed-use development located in the heart of Lexington’s Central Business District. The development, known as CentrePointe is to include a hotel, office tower, underground parking garage and retail space. He works for several years with local businessman and real estate investor, Joe Rosenberg, to acquire the full city block located at the corners of Main, Upper, Vine and Limestone streets. Throughout the economic downturn in the late 2000s, Dudley works with government officials and national and local architects to refine the design of the project. The existing buildings on the block are deemed unsafe and contaminated with asbestos. The block is razed and sod and horse fencing is installed to beautify the property. The property is used for many public events, such as charity polo matches, until the economy recovers and financing is finalized.

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After a 4-year absence, Marilyn Fralix rejoins The Webb Companies as Vice President of Accounting Services.


Dudley Webb returns to real estate development to focus on the new mixed-use development, CentrePointe.


Dudley Webb and Joe Rosenberg work to assemble the full city block located at Main, Upper, Vine and Limestone Streets.


Woodford Webb named Chairman of the Board of Commerce Lexington—the youngest-ever at the age of 40.


The existing structures on the block are deemed unsafe and the block is razed. Sod and horse fencing is installed to beautify the property.


The property is used for public events until financing is finalized.

The 2010s—City Center

Progress on the CentrePointe project would wait until 2014 for the economy to recover and financing to proceed. Sadly, company co-founder Donald Webb would not see the completed project. On July 19, 2013, Don passed away in Lexington from complications from Idiopathic Pulmonary Fibrosis (IPF) at the age of 74. Don’s influence reached throughout the Bluegrass region and it is estimated that over 1,000 mourners attended his funeral at Calvary Baptist Church in Lexington.

Dudley Webb continues to work tirelessly on the CentrePointe project and on January 7, 2014, construction finally starts on the first phase of the project—the 3-level, 700-parking space, underground garage. In 2017, local real estate developer and fellow Letcher County native, Phil Greer, along with his son Lee Greer and business partner Steve Pottinger, invest in the CentrePointe project and join the development team. Former Webb Companies project manager, Ralph Coldiron, who worked on most major downtown Webb projects in the 1980s, including the Lexington Financial Center, returns to coordinate the construction of the project. On April 19, 2018, the CentrePointe project is renamed City Center during the topping off ceremony attended by over 500 people. Construction continues over the next two years. By the end of the decade, construction on the $200 million mixed-use complex is complete.

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The Webb Companies Co-Founder and Co-Chairman, Donald W. Webb passes away.


Donald (posthumously) and Dudley Webb inducted into the Junior Achievement of the Bluegrass Hall of Fame.


Construction of the CentrePointe garage starts. Construction workers use explosives to break up the limestone slabs that lie below the ground surface.


Jeff Ruby signs first retail lease for a new Jeff Ruby’s Steakhouse in the CentrePointe complex.


Family matriarch, Elizabeth “Dottie” Webb passes away just shy of her 96 birthday in Lexington, Kentucky.


Phil Greer, Lee Greer and Steve Pottinger of the Greer Companies invest in the CentrePointe project and join the development team.


Project is renamed City Center during the Topping Off Ceremony with over 500 people in attendance.


Dudley Webb inducted into the Kentucky Entrepreneur Hall of Fame.


Construction on the $200 million City Center complex comes to an end.

The 2020s—The Future

On January 9, 2020, the new City Center mixed-use development opens to great fanfare. The ribbon cuttng ceremony is attended by Governor Andy Beshear, Mayor Jim Gray, former governors Martha Layne Collins and Steve Beshear, and many other notable Kentuckians. The grand opening gala helps to raise over $25,000 for the University of Kentucky Children’s Hospital in Lexington. The completed project includes a 700-space underground parking garage, a 214-room Marriott Hotel, a 120 all-suite Residence Inn, a state of the art office tower, skybar, luxury condominiums, and ground-level retail that includes a Jeff Ruby’s Steakhouse, Starbucks, Keeneland Mercantile and Italx restaurant.

Dudley Webb does not slow down with the completion of the City Center project. He is currently working on a $350 Million development with Lincoln Property Company to redevelop a 16 acre site next to historic Rupp Arena. The new project is to include an entertainment venue, retail shopping, luxury townhouses and parking facilities.

With the success of City Center, The Webb Companies and Greer Companies continue to co-develop additional properties in Lexington. The joint venture is currently developing a 28- acre, $40 Million retail shopping center titled The Fountains at Palomar at the corner of Man O War Boulevard and Harrodsburg Road in Lexington. In July 2022, Publix Supermarkets is announced as the anchor tenant of the new development that is scheduled for completion in late 2023. Most recently, the Webb/Greer team collaborated again to purchase 27.5 acres of land located at the corner of Citation Boulevard and Georgetown Road in August 2022. Plans are currently in development for a new retail shopping center to service Lexington’s rapidly growing northside.

After 50 years, The Webb Companies remains a family-run business. Dudley Webb, now in his late 70s, continues to serve as Chairman of The Webb Companies and works in the office every day. Woodford Webb, son of company co-founder Donald Webb, serves as President and is responsible management of the company’s vast real estate portfolio. They, along with their dedicated staff, continue to work with the same entrepreneurial spirit that the Webb brothers started out with all those years ago.

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City Center grand opening.


Construction starts on the new retail shopping center, The Fountains at Palomar, a joint venture with Greer Companies.


The Lexington Center Board awards the development of a 16 acre lot next to Rupp Arena to a joint partnership between The Webb Companies and Lincoln Property Company.


The Webb Companies and Greer Companies team up again to purchase 27.5 acres of land in Lexington’s north side for a proposed retail shopping center.


The Webb Companies celebrates its 50th Anniversary.