Dawgs By Nature
The embattled quarterback has settled one portion of his life
Cleveland Browns quarterback Deshaun Watson has made plenty of money. Watson and his fiancée Jilly Anais posted on Instagram that the wedding took place and the couple are officially married. The couple confirmed the news on social media on Thursday, July 3.
Watson was back in the news recently with a report that he could be healthy sometime in October, which could restart quarterback drama for a team that is expected to have four quarterbacks competing for the starting job in training camp.
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The former Miss Anais, age 29, is a Sports Illustrated Swimsuit model plus a social media influencer.
Watson wore a white long-sleeved shirt with “07.03.25” monogrammed on the sleeve. She wore a casual, plunging V-neck dress with her long hair pulled back in a scarf. It has been reported that the wedding took place on a yacht. Her engagement ring cost $2.5 million.
Watson was drafted by the Houston Texans in 2017 before being traded to the Browns in 2022. His total career earnings from NFL contracts alone equate to approximately $188.76 million as of 2025, with more money to come.
Watson was carted off the field after suffering a non-contact leg injury in the Week 7 game against division foe Cincinnati Bengals last year. It was later confirmed as an Achilles tear, which required surgery. He was subsequently placed on IR. In January of 2025, he re-ruptured the Achilles tendon and underwent more surgery.
The status of his playing availability for the upcoming season remains in doubt. He has been seen working out frequently at the Browns’ Berea facility.
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After last season, the Browns only had one healthy QB on the roster, Dorian Thompson-Robinson. But he was traded to the Philadelphia Eagles for former first-round pick Kenny Pickett. Then Browns GM Andrew Berry re-signed seasoned veteran Joe Flacco and drafted Dillon Gabriel of Oregon and Shedeur Sanders from Colorado. All the while, Watson was listed as a roster member.
Could Watson return?
Dawgs by Nature staff writer Thomas Moore penned this sentiment in his article on the subject:
“But there is no plausible scenario where Watson takes another meaningful offensive snap with the Browns.”
It has been mentioned that Watson could actually return to the practice field sometime in October, unless doctors do not clear Watson. Traditionally, the Browns only keep three QBs on the roster. Right now, with Watson included, they have five under contract.
But for now, for Watson, life is pretty friggin’ good.
So, there is a bit of an issue with the quarterback room going forward. Who do they cut? How can they keep all five? Or do they even want to try this maneuver? Even the act of retaining four signalcallers is a tough ask.
The best suggestion is to have HBO’s “Hard Knocks” reality TV show come in...
