Deshaun Watson’s future on the field with the Cleveland Browns remains uncertain, but off the field, his life seems to be progressing in a new direction. The Browns’ quarterback, who is recovering from a ruptured Achilles, has recently taken steps in his personal life, announcing his engagement to his long-time girlfriend, Jilly Anais. The couple’s joyful moment was shared by Anais on social media in March, followed by another announcement this week, with the caption “The Watsons… coming soon,” as they posed together beside a yellow Ferrari.

However, despite these positive personal developments, Watson’s professional trajectory with the Browns appears to be at a crossroads. The franchise, which made a high-profile trade for Watson in 2022, is now grappling with the fallout from that decision. Watson, who was acquired in exchange for a substantial amount of draft capital and a record-breaking $230 million fully guaranteed contract, has yet to fulfill the lofty expectations set by the Browns.

The off-field controversies surrounding Watson, along with injuries and a lack of consistency on the field, have cast doubt on his future in Cleveland. Watson, who was expected to lead the Browns into a new era, has instead spent much of his time with the team sidelined. After suffering a ruptured Achilles in October, Watson re-aggravated the injury during his rehabilitation, requiring a second surgery in January. As a result, he is expected to miss much, if not all, of the upcoming season.

In Watson’s absence, the Browns have moved forward, actively building a new quarterback room. The team has signed veterans Joe Flacco and Kenny Pickett while also adding two promising rookies to the mix — Shedeur Sanders, who was selected in the fifth round, and Dillon Gabriel, drafted in the third. Cleveland’s decision to bring in two rookie quarterbacks was a bit of a surprise, but Browns general manager Andrew Berry explained that the team saw great value in Sanders, who had been projected by many to go in the first round.

We didn’t necessarily expect to select two quarterbacks,” Berry said after the draft. “But as we talk about, we do believe in best player available, we do believe in positional value, and we didn’t necessarily expect him to be available in the fifth round. We love adding competition to every position room and adding him to compete with the guys that are already in there.”

While Watson’s future is unclear, it’s evident that the Browns are preparing for a quarterback competition that could have lasting implications on the team’s success. Even if Watson does return to full health, the crowded quarterback room and the addition of two high-profile rookies signal that his time as the Browns’ starting quarterback may be coming to an end.

Owner Jimmy Haslam recently acknowledged the trade for Watson as a failure for the first time, taking responsibility for the decision at the league’s annual meeting. “We took a big swing-and-miss with Deshaun,” Haslam admitted. “We thought we had the quarterback; we didn’t. And we gave up a lot of draft picks to get him, so we’ve got to dig ourselves out of that hole.”

With the Browns looking to rebound from the missteps of the Watson trade, the focus is shifting to their next solution at quarterback. As the quarterback competition heats up with Gabriel, Sanders, and veterans Flacco and Pickett, all eyes will be on Cleveland to see if they can find a quarterback who can lead the team back to success. Whether Watson remains a part of that future or not remains to be seen, but for now, his role in Cleveland is more uncertain than ever.