Deshaun Watson’s $230M NFL Deal and Lavish $2.5M Engagement Ring for Jilly Anais

Deshaun Watson’s $230M NFL Deal and Lavish $2.5M Engagement Ring for Jilly Anais.

Deshaun Watson has built an impressive career in the NFL, securing some of the biggest contracts in football history. Now, he’s making headlines again—not just for his on-field achievements, but for his lavish $2.5 million engagement ring for longtime girlfriend Jilly Anais.

Watson’s Record-Breaking NFL Contract

Watson’s professional football journey began in 2017, when he was drafted by the Houston Texans and signed a four-year contract worth $13.85 million, including an $8.21 million signing bonus. His talent quickly became evident, leading to a massive four-year, $156 million contract extension in 2020, solidifying his status as one of the league’s top quarterbacks.

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In 2022, Watson’s career took another major turn when he was traded to the Cleveland Browns. He then signed a historic five-year, $230 million fully guaranteed contract, the largest guaranteed deal in NFL history. This contract boosted his annual salary to $46 million, bringing his total career earnings from NFL contracts alone to approximately $188.76 million as of 2025.

Fluctuating Endorsement Deals

While Watson’s NFL earnings continue to soar, his endorsement portfolio has seen ups and downs. He previously had high-profile partnerships with brands like Nike and Beats by Dre, but many companies distanced themselves from him following allegations of sexual misconduct.

As a result, his endorsement earnings dropped significantly, with recent reports estimating he now makes around $1 million annually from sponsorships. However, given his high-profile career and continued success, there is potential for future endorsements to resurface.

Watson & Jilly Anais: A Love Story Amid Challenges

Despite public scrutiny, Watson and Jilly Anais have remained steadfast in their relationship since they began dating in 2019. Anais, a Houston native, has made a name for herself as a singer, actress, model, and cookbook author.

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The couple has faced numerous challenges, yet they have remained supportive of each other, showing resilience in the face of adversity. Their recent engagement announcement, highlighted by Watson’s stunning $2.5 million ring, is a testament to their strong bond and commitment.

A Bright Future Ahead

With his record-breaking NFL contract, ongoing career success, and now his engagement to Jilly Anais, Deshaun Watson is looking toward a promising future. His ability to navigate professional and personal challenges with determination proves his resilience both on and off the field.

As Watson continues to build his legacy in the NFL, his relationship with Anais also embarks on a new chapter. Their love story, filled with ups and downs, now moves forward with optimism, commitment, and a shared vision for the future.