Total Pro Sports
Deshaun Watson’s closest pals took him out for a wild bachelor party ahead of his wedding with longtime girlfriend, Jilly Anais.
The veteran quarterback and Anais announced their engagement via Instagram back in March. They have been together since 2019, when Deshaun Watson was in his third season as a pro.
Per TMZ Sports, Watson’s close circle took him out for a rowdy bachelor party in Miami, Florida, ahead of his big day with Jilly Anais. The group started by driving around town in rented luxurious cars, the outlet reported.
To top off the evening, the group reportedly spent about $20,000 on a lucrative three-course dinner at the Papi Steak restaurant in Miami Beach. The dinner was loaded seafood items, too.
Deshaun Watson Goes All Out For Bachelor Party, Luxury Cars, Steak & Fire! | Click to read more 👇 https://t.co/OzkrjsSPzL
— TMZ Sports (@TMZ_Sports) June 9, 2025
Deshaun Watson has two years remaining on the $230 million fully-guaranted deal he signed with the Browns in 2022. The AFC North club gave up a king’s ransom to the Houston Texans to acquire Watson, including a trio of first-round picks that the Texans would use to build up a long-term title contender.
Three years later, however, the deal has gone down as one of the most lopsided in NFL history in favor of the Texans.
The trade and $230 million deal has been a colossal failure for Cleveland. Watson was suspended for the first 11 games of 2022 after being accused of sexual misconduct by more than two dozen women, and season-ending injuries limited him to 13 total games over the 2023 and ’24 seasons.
Watson is expected to miss most, if not all, of 2025 recovering from an Achilles tear he suffered last season. Watson re-ruptured the Achilles during his recovery and required a second surgery to repair it.
On the field, he hasn’t been productive whatsoever. The 2017 first-round pick has gone just 9-10 as the Browns’ starting QB with 19 touchdowns and 12 interceptions.
