Deshaun Watson Announces Engagement to Longtime Girlfriend Jilly Anais

Cleveland Browns quarterback Deshaun Watson has taken a big step off the field by announcing his engagement to longtime girlfriend, Jilly Anais. The couple shared the exciting news on Instagram on Sunday, complete with a photo of Anais’ stunning ring and a cheeky caption: "Mrs. Watson Loading…"

Watson himself commented "MORE GLORY" on the post, which feels equally fitting for a wedding announcement and a sports mantra. The engagement is certainly a bright moment for the 29-year-old athlete, who has faced a challenging few years on the professional front.

Despite this personal milestone, questions loom over Watson’s future with the Browns. The quarterback suffered two ruptures to his right Achilles tendon within three months, initially injured during an October game against the Cincinnati Bengals and then again in January. His return to the field for the 2025 season remains uncertain.

Adding to the drama, the Browns recently restructured Watson’s contract—for the second time in three months—to clear nearly $36 million in cap space, according to the Associated Press. Watson’s fully guaranteed $230 million contract, signed in 2022, has yet to yield consistent on-field results. In fact, he’s only played 19 games for Cleveland due to injuries, including a shoulder injury in 2023 and the Achilles issues this past season.

Meanwhile, the Browns appear to be hedging their bets at the quarterback position. The team recently traded for Kenny Pickett from the Philadelphia Eagles and even hosted free agent Russell Wilson last week. It seems they’re gearing up for a potentially Watson-less season.

While Watson’s professional future may be uncertain, his personal life appears to be on solid ground with Anais by his side. And hey, if "MORE GLORY" applies to love as well as football, then Watson might just be winning after all.