Pam Bondi Has A Scandalous Age-Gap Relationship Under Her Belt

U.S. Attorney General Pam Bondi has a messy dating history, and it includes one of those age-gap relationships so common among politicians. She was married and divorced twice before the age of 37. Her first marriage to Garret Barnes was short-lived, lasting less than two years after their 1990 wedding. Her second marriage to Scott Fitzgerald lasted longer; she was married to the Tampa businessman from 1997 to 2002. In 2017, she started dating her long-term partner and real estate investor, John Wakefield.

Before her relationship with Wakefield, she had a mysterious age-gap relationship with Tampa ophthalmologist Greg Henderson, who was 15 years her senior. When they first started dating, Henderson was already a widower with four children after his wife, Kathy, passed away in 2002. Given their age difference, Henderson had lived a much different life than Bondi, who never had children. 

Bondi has been notoriously private about her romantic life throughout her many different relationships, especially with her two ex-husbands, whom the media knows very little about. This left the public to speculate just how far Bondi and Henderson's relationship ultimately went before it fell apart. Senator Paula Dockery ignited marriage rumors between them in a series of 2012 Facebook posts captioned, "The blushing bride serving punch to her friends on Cayman Air," and, "The plane is filled with her wedding party," hinting at their upcoming nuptials (via The Palm Beach Post). While the media reasonably suspected the pair may have held a secret wedding in 2012, sources can only confirm that they were engaged at that time. 

Pam Bondi and Greg Henderson sparked rumors of a secret marriage in 2012 after The Palm Beach Post reported that the couple traveled to the Cayman Islands with other politicians for their wedding. The governor of Florida at the time, Rick Scott, was reported to be in attendance with his wife. Despite the rampant rumors, the Tampa Bay Times reported that they canceled the destination wedding in Grand Cayman because they wanted to get married in a Baptist church in Tampa. "We are enjoying a happy and blessed trip and are deeply in love with each other," Bondi stated at the time. The public still knows very little about the demise of Bondi and Henderson's significant age-gap relationship, but rumors about their split exploded in 2015. While the exact timeline of their engagement and split remains a mystery, their breakup was eventually confirmed by Bondi's public relationship with John Wakefield. 

Public confusion over Bondi's marital status has not died down in her relationship with Wakefield. Even though Bondi and Wakefield have not confirmed they are married, President Donald Trump added to secret marriage rumors again by referring to Wakefield as Bondi's husband during her swearing-in ceremony as attorney general in February 2025. "I just want to introduce her very, very handsome husband. I hate being around him. He looks too good," Trump said, per People. "He's been a tremendous factor with Pam and just a beautiful relationship." Despite the media's attempts at pinpointing their current relationship status, Bondi and Wakefield have yet to even confirm an engagement.