Time flies when you’re the most debated man in Texas. It feels like only yesterday Tony Romo went down in a preseason game against Seattle, and a fourth-round kid from Mississippi State stepped into the huddle. But that was a lifetime ago in football years. If you’re wondering how long has dak been with the cowboys, the answer is 10 seasons. As of 2026, Dak Prescott has spent a full decade under the brightest spotlight in professional sports.
Ten years.
Think about that. In NFL terms, a decade is an eternity. Most players are lucky to survive three years. Dak hasn't just survived; he’s rewritten the record books in Dallas while navigating enough drama to fill a dozen soap operas.
The Unlikely Arrival in 2016
When the Cowboys drafted Rayne Dakota Prescott with the 135th overall pick in 2016, nobody—literally nobody—expected him to be the face of the franchise. Jerry Jones was actually trying to trade up for Paxton Lynch or Connor Cook. Imagine that alternate reality for a second.
Instead, a series of draft-day "failures" led them to Dak. Then, Kellen Moore broke his ankle. Then, Tony Romo’s back gave out. Suddenly, the rookie was QB1.
He didn't just play; he dominated. He led the team to a 13-3 record, won Offensive Rookie of the Year, and basically forced a franchise legend into retirement. It was one of the most efficient rookie seasons in the history of the league. He looked like a veteran from day one, showing a poise that usually takes years to develop.
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Breaking Records and Romo’s Shadow
For the longest time, Tony Romo was the standard for modern Cowboys passing. But records are meant to be broken. In late 2025, Dak officially surpassed Romo to become the Cowboys' all-time leading passer.
He did it on a Sunday against the Eagles. Fitting, right?
A 9-yard completion to George Pickens pushed him over the 34,183-yard mark. It was a quiet moment for a guy who has spent how long has dak been with the cowboys facing criticism for every single mistake. People love to talk about the interceptions or the playoff record—which, honestly, is a bit of a sore spot at 2-5—but you can’t argue with the volume of production.
He’s finished near the top of the league in passing yards and touchdowns multiple times. He’s been a Pro Bowler in 2016, 2018, and 2023. He even snagged a Walter Payton Man of the Year award in 2022. He’s the engine of that offense. When he’s on, the Cowboys look unstoppable. When he’s off, the internet melts down.
The Gritty Reality of the Injuries
You can't talk about his tenure without talking about the physical toll. It hasn't been all sunshine and 400-yard games.
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- 2020: The gruesome ankle dislocation that ended his season in Week 5.
- 2022: A thumb fracture that sidelined him for five games.
- 2024: A massive hamstring avulsion where the tendon literally tore off the bone.
That 2024 injury was brutal. He missed half the season and had to watch from the sidelines as the team struggled to a 3-6 start. Critics said he was washed. They said the contract was a mistake. But he came back in 2025 and threw for over 4,500 yards and 30 touchdowns. The guy is nothing if not resilient.
The $240 Million Question
Money is always part of the Dak Prescott conversation. It's inescapable. In September 2024, he signed a massive four-year, $240 million extension. That put him at an average of $60 million per year—the highest in the league at the time.
Why did Jerry Jones pay that much? Because finding a franchise quarterback is hard. Finding one who can handle the Dallas media for a decade is nearly impossible.
As we look at the 2026 cap situation, his hit is a staggering $74 million. That’s a lot of cap space tied up in one player. It forces the front office to be perfect everywhere else. They’ve had to make tough calls on other veterans just to keep the lights on. But that’s the price of entry for a top-tier QB in today’s NFL.
What the Stats Don’t Tell You
If you just look at the 2-5 playoff record, you’re missing the nuance. Honestly, football is a team game, even if the QB gets all the blame.
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Take the 2016 playoff loss to Green Bay. Dak was phenomenal. He threw for three touchdowns and led a massive comeback, only for Aaron Rodgers to pull a miracle out of his hat in the final seconds. Or 2023 against the Packers—yeah, Dak had two bad picks early, but the defense allowed Jordan Love to have a nearly perfect passer rating.
The pressure in Dallas is different. It’s heavier. Every throw is scrutinized like it’s a matter of national security. Some players fold under that. Dak hasn’t. He’s remained the leader of that locker room through coaching changes, roster overhauls, and personal tragedy.
Looking Ahead to 2026 and Beyond
So, we know how long has dak been with the cowboys, but how much longer will he stay?
His current deal runs through 2028. By the time it’s up, he’ll have been the starter for 13 seasons. That would put him in the same rarified air as Troy Aikman and Roger Staubach in terms of longevity.
The goal remains the same: the Super Bowl. That’s the only thing left to do. He has the yards. He has the money. He has the records. But in Dallas, you’re measured by rings.
Actionable Insights for Fans and Analysts:
- Appreciate the Stability: Since 2016, many teams have cycled through half a dozen quarterbacks. The Cowboys haven't had to worry about the most important position on the field for a decade.
- Contextualize the Playoff Record: Look at the defensive performance in those losses. Usually, when the Cowboys lose in January, the defense is giving up 30+ points.
- Watch the Cap: Keep an eye on March 15, 2026. That’s when his 2027 salary becomes fully guaranteed. It’s a key date for how the Cowboys manage their roster.
- George Pickens Connection: The chemistry between Dak and Pickens in 2025 was a game-changer. If that continues into 2026, the offense could reach a new level of explosiveness.
The journey from a fourth-round "project" to a $240 million franchise icon is one of the most fascinating stories in modern sports. Whether you love him or hate him, Dak Prescott is the defining figure of this era of Dallas Cowboys football.