[8][9][10] Benson began her career in receptionist and secretarial positions while doing interior design before buying and renovating businesses with her second husband, Thomas "T-Bird" Bird.

[14] Benson is one of ten female NFL owners, including Sheila Ford Hamp (Detroit Lions), Kim Pegula (Buffalo Bills), Carol Davis (Oakland Raiders), Denise DeBartolo York (San Francisco 49ers), Amy Adams Strunk (Tennessee Titans), Virginia Halas McCaskey (Chicago Bears), Janice McNair (Houston Texans), Jody Allen (Seattle Seahawks), and Dee Haslam (Cleveland Browns).

[15] Benson and Allen (Portland Trail Blazers) are two of five female owners in the NBA, along with Jeanie Buss (Los Angeles Lakers), Miriam Adelson (Dallas Mavericks) and Ann Walton Kroenke (Denver Nuggets).

[17][18] Tom Benson's daughter and grandchildren filed lawsuits challenging his decision to name Gayle his heir, questioning his mental competency.

[28][29][30] According to the New York Times, under Benson's leadership "the Saints and the archdiocese (began) working together to temper the fallout from a flood of sexual abuse accusations made against priests and church employees.

The efforts included "working closely with the archdiocese in attempting to solicit positive media coverage of the church and burnish the image of Archbishop Aymond, even writing talking points for him.

[31] In July 2017, it was announced that Tom and Gayle Benson had finalized an agreement to buy a majority share of Dixie Brewing Co.[32] The company's brewery plant had been damaged and closed after Hurricane Katrina.

[1][8] Her second marriage was to Thomas "T-Bird" Bird, on February 14, 1977, in South Pass, Plaquemines Parish, Louisiana, which ended in a divorce on June 25, 1987.