There is a version of this story where Dak Prescott enters the spring of 2026 as one of the most luckiest men on Earth, not just in professional football.
Prescott is 32, healthy for the first time in years, signed to a four-year $240 million contract, the richest contract in NFL history at the time, and one month away from marrying the woman he called the love of his life at a destination wedding in Italy.
That version of the story died Saturday night.
TMZ Sports reported that Prescott and fiancée Sarah Jane Ramos have broken up just one month before their Italy wedding.
A blowup argument during their joint bachelor and bachelorette parties in the Bahamas ended the engagement. Sarah Jane Ramos was the one to pull the plug.
It is the latest entry in what has become one of the most difficult stretches of Prescott’s life. It did not arrive alone.
The Dallas Cowboys Season That Went Sideways
The 2024 NFL season was supposed to be the year Prescott cemented himself as one of the elite quarterbacks of his generation.
Instead it ended in Week 9 with him on the turf in Atlanta, his right hamstring tendon partially torn from the bone.
“Didn’t think much of it,” he said after the game. “Then the next play, I felt a pull. That’s something I never felt. It was tough to walk on it at that point. I asked if I could make it worse. The medical staff said I wouldn’t be able to protect myself. I wanted to get out there and compete. I wanted to get out there and fight.”
Cowboys owner Jerry Jones announced surgery the following week.
Prescott flew to New York for the procedure and missed the remainder of the season.
At the point of his injury, he had thrown for 1,978 yards, 11 touchdowns and 8 interceptions, a passer rating of 86.0 that was the worst of his career.
The Cowboys went 3-5 with him and 4-5 without him, missing the playoffs for the first time in four years.
The Return That Still Wasn’t Enough
Prescott attacked the 2025 season with everything he had.
He had no days off in training camp. He told reporters in the offseason: “I know that a better version of me is on the other side, so that’s just the way I’ve approached this whole offseason and this whole rehab process.”
Sarah Jane backed him publicly throughout the year. In a November 2025 interview with Sports Illustrated, she said:
“Dak’s in really good shape. I’m really proud of him for the work he put in this offseason and really recovering from his injury from last season. He’s in better shape than when I met him three years ago, substantially better shape, and his head space is so good.”
He stayed healthy all 17 games in 2025, a genuine victory given what the previous year had looked like.
He passed Tony Romo as the Cowboys’ all-time leading passer, reaching 35,989 career yards.
He called finishing the season healthy “a blessing” and told reporters he had already started his offseason training earlier than any previous year.
But the Cowboys still missed the playoffs. Again.
Two consecutive seasons without a postseason appearance for one of the most scrutinized franchises in American sports.
The losses piled up. The questions about Prescott’s ability to win the big game, a criticism that has followed him his entire career despite being one of the league’s best regular-season quarterbacks, grew louder.
“Disappointing,” is how Prescott himself described the 2025 season.
The $240 Million Man Without A Ring
The cruel irony of Prescott’s situation is that he is carrying the heaviest contract in NFL history and has almost nothing to show for it in terms of postseason success.
The Cowboys signed him to that four-year, $240 million extension in September 2024, the same season he tore his hamstring in Week 9.
The contract was supposed to be a statement of commitment. Instead it became a weight.
He has four division titles and four Pro Bowl appearances in his career. He finished second in NFL MVP voting in 2023. He has broken virtually every passing record in Cowboys history. And he has never been to a Super Bowl.
Two Daughters, A Cancelled Wedding, And What Comes Next
The personal fallout from Saturday’s news is significant.
Prescott and Ramos have two daughters, MJ, who is 2 years old, and Aurora, who is nearly 10 months old.
TMZ reports the relationship is beyond repair. The focus going forward will be co-parenting.
He was supposed to get married next month. He was supposed to fly to Italy and exchange vows with the woman he hid a $1 million ring inside a fake golf ball to propose to.
He was supposed to start the 2026 NFL offseason as a husband and a father of two.
Instead he starts it as a single father navigating a broken engagement, a cancelled wedding, and a co-parenting arrangement for two toddlers, all while trying to figure out how to finally get the Dallas Cowboys back to where they need to be.
Prescott has come back from a fractured ankle. He has come back from a torn hamstring. He has come back from every football setback thrown at him.
This one is different.
