NFL Star Deshaun Watson Proposes to Girlfriend Despite Controversial Past, Massive Diamond Ring Seals the Deal

Cleveland Browns quarterback Deshaun Watson is officially engaged. Over the weekend, he proposed to his longtime girlfriend, Jilly Anais, and she happily said yes. The couple, who have been together since 2019, announced their engagement on social media, showcasing Anais’ massive diamond ring.

While the engagement should be a joyous occasion, it comes at a time when Watson’s name is still surrounded by controversy. Over the past few years, the quarterback has faced serious allegations of sexual misconduct from more than two dozen massage therapists.

These accusations led to multiple lawsuits, damaging his reputation despite many cases being settled out of court. Even as Watson continues to play in the NFL, his legacy remains clouded by the scandal.

Adding to the uncertainty, Watson’s football career is once again in jeopardy. Earlier this year, it was revealed that he reinjured his Achilles, an issue that first surfaced in a game against the Cincinnati Bengals in October of last season.

Due to the severity of the injury, he is expected to miss most—if not all—of the 2025 NFL season.

With his future on the field uncertain and his past still looming, Watson’s engagement has sparked major discussions, particularly about his relationship with Anais and the luxurious ring that has captured public attention.

Watson and Anais’ romance has faced public scrutiny since allegations against the quarterback first emerged. The first lawsuit was filed on March 16, 2021—coincidentally, exactly four years before their engagement announcement.

Despite the scandal, Anais has stood by Watson, supporting him through both his legal troubles and career setbacks.

Anais, a social media influencer, singer, and model, has built her own brand outside of her relationship with Watson. However, her unwavering support of the quarterback has made her a target of criticism.

Many have questioned why she remained by his side despite the allegations, while others have accused her of prioritizing his wealth and status over ethics.

Regardless of public opinion, Anais has made her stance clear—she is committed to Watson, no matter the controversy. Now, with an extravagant diamond ring as a symbol of their engagement, she has further solidified her decision to stay with him.

As expected, the engagement announcement has received mixed reactions. Fans and fellow athletes flooded the couple’s social media with congratulatory messages, celebrating the milestone.

However, it wasn’t long before critics chimed in.

Social media erupted with debates, with some users bringing up Watson’s past legal issues and questioning Anais’ motives. The sheer size of the diamond ring became a hot topic, with many speculating that Watson’s financial success played a major role in securing the engagement.

Some fans defended the couple, arguing that their relationship has lasted for nearly six years, proving their bond is real. Others suggested that Anais has remained loyal despite the public backlash, which could be a sign of genuine love rather than financial motivation.

However, Watson’s engagement does little to erase the concerns surrounding him. His name is still linked to controversy, and his NFL career remains in limbo due to his latest injury.

Many have wondered if this public display of commitment is, in part, an effort to shift the narrative away from his troubled reputation.

Beyond his engagement, Watson’s professional future remains uncertain. After signing a $230 million fully guaranteed contract with the Browns, his time in Cleveland has been anything but smooth.

Between his suspensions, injuries, and inconsistent performances, he has yet to justify the massive investment the Browns made in him.

The latest Achilles reinjury is another setback, raising concerns about his ability to ever return to elite quarterback form. For Browns fans, his absence in 2025 is frustrating, as many had hoped this season would mark a turning point in his career.

Instead, Watson is set to spend another year on the sidelines, leaving Cleveland’s quarterback situation in doubt once again.

With his time away from the field, Watson will likely turn his focus to wedding planning. Given the couple’s love for luxury, their wedding could be an extravagant affair, featuring high-profile athletes, celebrities, and lavish details.

However, whether the public will embrace their marriage—or if Watson will ever fully recover his image—remains to be seen.

For now, Deshaun Watson and Jilly Anais appear to be shutting out the noise, focusing on their future together. While his NFL career is uncertain, his engagement makes one thing clear—he has found someone who is willing to stand by him, regardless of the controversy.

Whether this engagement marks a fresh start or simply another chapter in Watson’s complicated legacy is something only time will tell. But one thing is undeniable—the massive diamond ring has stolen the spotlight, ensuring that Watson’s engagement remains a major talking point in both the sports world and beyond.