Real estate career In 1989, Bennett co-founded and joined Remington Hotels, a hotel company co-owned by his father. He was CEO of Braemar Hotels & Resorts until 2016 and since 2013 has remained its chairman. He is also the founder of Ashford, a company that advises both Braemar Hotels & Resorts and Ashford Hospitality Trust, two publicly traded
real estate investment trusts. Bennett was the CEO of Ashford Hospitality Trust from its founding until 2017, and he remains the firm's chairman. In 2020, a number of large companies were criticized for receiving funds distributed through the
Paycheck Protection Program (PPP) during the
COVID-19 pandemic. Bennett's Ashford company received $56 million, Ashford announced in May 2020 that it would return the money after the company received backlash. Bennett forfeited 25% of his 2019 earned bonus, took a 20% cut in salary which he later took in stock only. Bennett remained chairman of the board of Ashford Hospitality Trust after an attempt to replace him in 2024 by activist investor Blackwells Capital. He did not receive enough votes to be re-elected to the board at the company's annual shareholder meeting. The remaining board members followed the recommendation of the board's nominating and corporate governance committed and declined to accept Bennett's resignation.
Publishing career In 2021, Bennett launched and became publisher of the
Dallas Express, a conservative news website in Dallas, Texas. It is unrelated to the
African-American Dallas newspaper of the same name that published from 1892 to 1970. That year, Bennett sued
The Dallas Weekly, alleging
libel over its unfavorable descriptions of the new
Dallas Express, and prevailed at trial, although the case was dismissed on appeal in 2022 in
Monacelli v. Bennett. In 2024, the
Texas Observer reported that Bennett had retained the services of Crowds on Demand, a group known for offering protesters-for-hire, to create a number of advocacy groups that were routinely quoted in articles in Bennett's
Dallas Express without their disclosing behind-the-scenes connections. Bennett admitted that his company Ashford had hired Crowds on Demand but otherwise denied the findings of the
Texas Observer report, which quoted Emily Bell, the founding director of the Tow Center for Digital Journalism at Columbia Journalism School, who said that the Dallas Express has violated basic journalistic ethics and is deceptive: “Effectively, the business model here is deception. It’s not just about them being partisan. It’s about them being dishonest and crossing basic lines of journalism. They’re not even doing journalism. They’re doing P.R., political advertising, or persuasion campaigns.” == Political involvement ==