While the Cleveland Browns continue navigating one of the most complicated quarterback situations in recent memory, owner Jimmy Haslam made headlines for his presence at a very different kind of event.
Deshaun Watson married longtime girlfriend and Sports Illustrated Swimsuit model Jilly Anais in a private yacht ceremony off the coast of Miami.
The lavish celebration marked their sixth anniversary as a couple and featured designer gowns, custom suits, and matching diamond-studded rings valued at over $3 million.
“Browns Jimmy Haslam was in attendance for QB Deshaun Watson’s wedding. Some other notable people in attendance were Jerry Jeudy, DeAndre Hopkins, and Josh Dobbs,” Grant Puskar shared on X.
#Browns Jimmy Haslam was in attendance for QB Deshaun Watsons wedding.
Some other notable people in attendance were Jerry Jeudy, DeAndre Hopkins and Josh Dobbs. pic.twitter.com/Y0P8zPIAnF
— Grant Puskar (@grant_puskar_) July 13, 2025
The timing of Haslam’s appearance adds intrigue to an already complex relationship.
Just months earlier, the Browns co-owner publicly described the Watson trade as a “big swing-and-miss,” acknowledging the front office’s miscalculation in offering $230 million guaranteed to a player who has appeared in only 19 games over three years.
Watson faces an uncertain future with the franchise as he recovers from his second Achilles surgery.
The quarterback is unlikely to play in 2025, further clouding his standing with the organization that invested heavily in his services.
Haslam’s wedding attendance sparked considerable discussion among fans and the media.
The gesture could represent personal support for a player battling injuries and controversy, or it might signal the organization’s continued commitment despite public frustrations.
Whether it shows a change of heart or just mutual respect, it adds another twist to this closely followed NFL relationship.
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