Cleveland Browns quarterback Deshaun Watson has made headlines with a major personal and professional announcement. On March 16, 2025, Watson revealed his engagement to longtime girlfriend Jilly Anais, while also addressing his NFL future and contract restructuring.
Engagement to Jilly Anais
Watson and Jilly Anais, a model, singer, and social media influencer, shared their engagement news on Instagram, posting a joint announcement captioned, “Mrs. Watson Loading…” The couple, who have been together for several years, have frequently shared their relationship milestones online, making this a moment of celebration amid Watson’s ongoing NFL challenges.
Anais, known for her successful music career and social media presence, has been a supportive figure in Watson’s life, especially throughout his recent injuries and legal battles. The engagement news has been met with an outpouring of congratulations from fans and fellow NFL players.
NFL Career & Injury Setback
Watson’s engagement comes at a pivotal time in his career. The Browns quarterback suffered a re-rupture of his right Achilles tendon, an injury that may keep him sidelined for the entire 2025 NFL season. The injury is the latest in a string of setbacks that have plagued his time with the Browns since signing a historic $230 million fully guaranteed contract in 2022.
Watson has struggled with injuries, inconsistent performances, and off-field controversies, leading to questions about his future with the Browns. Despite the concerns, Cleveland’s front office remains committed to Watson, with team executives hoping for a strong recovery ahead of the 2026 season.
Browns Free Up Cap Space
In response to salary cap constraints, the Browns and Watson agreed to restructure his massive contract, converting $44.7 million of his 2025 salary into a signing bonus. This move created $35.75 million in cap space, allowing the Browns greater financial flexibility to make offseason acquisitions and strengthen the roster.
The contract restructuring signals that the Browns are still banking on Watson as their franchise quarterback, despite his recent struggles. However, analysts suggest that 2026 could be a make-or-break season for him in Cleveland, depending on his injury recovery and on-field performance.
Watson’s Journey with the Browns
Watson’s tenure with the Browns has been anything but smooth. Since being traded from the Houston Texans in 2022, he has played in only a handful of games due to a combination of injuries and an 11-game suspension related to sexual misconduct allegations.
Despite controversy and criticism, Watson has remained focused on returning to form, and the Browns continue to build around him, hoping he can lead the team to its first Super Bowl appearance in franchise history.
What’s Next for Watson?
As Watson prepares for rehabilitation and recovery, fans and analysts are left wondering:
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Will he return to full strength in 2026?
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Can he justify the Browns’ massive financial commitment?
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How will his engagement and personal life influence his future?
For now, Watson is celebrating a major personal milestone with Jilly Anais, while the Browns prepare for another season without their high-priced quarterback under center. Only time will tell if he can bounce back and live up to the expectations that once made him one of the NFL’s top quarterbacks.