Pam Bondi’s relationship history has been pretty eventful, especially before she joined forces with Donald Trump in 2019 as a White House staff member during his first term. The Florida native got married and divorced twice between 1990 and 2002, and after taking time to focus on her career, Bondi had an age-gap romance in the early 2010s. She was engaged to ophthalmologist Greg Henderson, who is 15 years her senior, while she served as Florida’s attorney general. Despite how common massive age gaps are for political couples, Bondi’s age gap with Henderson seemed more drastic since he was married for two decades before his wife died in 2002, and his four children were adults during the engagement.
Bondi telling the Tampa Bay Times about the engagement in 2011 meant that she and Henderson were pretty serious about each other. The former couple even sparked marriage rumors in 2012 as their vacation to the Cayman Islands circulated on the web. Former Florida state senator Paula Dockery shared a Facebook post with the caption, “The blushing bride serving punch to her friends on Cayman Air,” (via The Palm Beach Post). The couple wearing a white dress and a suit, respectively, didn’t make the trip look like anything other than a wedding. However, Bondi and Henderson told the Tampa Bay Times that a destination wedding never occurred. Henderson said, “We are enjoying a happy and blessed trip and are deeply in love with each other.”
Bondi’s current match seems to be more aligned with her in age
Ultimately, Pam Bondi and Greg Henderson didn’t last because their engagement didn’t end in marriage. Bondi is currently partnered with private equity owner John Wakefield, who seems much closer to her in age. While his exact year of birth is unknown, Wakefield earned a bachelor’s degree in English in 1994 from the College of Charleston and a master’s in international business in 1998 from the Thunderbird School of Global Management. Bondi was born in 1965, and she earned her bachelor’s degree in 1987 and her law degree in 1990.
She might be slightly older than her new beau, but the age difference is nowhere near her last serious relationship. In middle age, Bondi and Wakefield can relate to each other as they pursue their endeavors in the last years of their careers. While others might think Bondi and Wakefield’s extreme privacy is a red flag, the ambiguity of their relationship status in the public eye could make their connection more enjoyable. Henderson, on the other hand, might have retired from ophthalmology before Bondi started working with Trump. If Bondi entered a third marriage with Henderson, the different life stages might have caused a strain in their relationship.
