Dak Prescott Admits “Monkey on the Back” Gets Bigger Every Year the Cowboys Don’t Win Super Bowl

The Dallas Cowboys QB Dak Prescott has a postseason record of 2-5 from seven appearances.

Dak Prescott Admits “Monkey on the Back” Gets Bigger Every Year the Cowboys Don’t Win Super Bowl

Dak Prescott (Image via Sports Illustrated)

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After a decade in Dallas, Dak Prescott’s tenure with the Dallas Cowboys has been defined more by unfulfilled promise than postseason glory. In the past ten seasons, the franchise has managed only five playoff appearances, leaving expectations far from met.

The 32-year-old recently addressed the lack of postseason success in an interview with Clarence Hill of ALLDLLS. Prescott maintained that every year the Cowboys don’t make the Super Bowl adds to the growing chip on his shoulder.

Monkey, gorilla, you know, gets bigger each year that we don’t make it. And that’s real. It’s one of those things. You get here as a rookie and everybody thinks they can win the Super Bowl. and they think how easy it is.

Dak Prescott said

Prescott’s perspective has changed over the course of his career, expressing frustration mixed with hope. Furthermore, he admitted that the early success as a rookie had led him to believe that more opportunities were on his way. However, he has since realized that it is not easy to make it to the Super Bowl, expressing his hurt over the fact that he hasn’t had the level of team or personal success he hoped for.

And when you have a year like I did as a rookie, you think you going to have multiple opportunities. And now in Year 10, having opportunities and not doing what you wanted as a team and individually, it hurts. And every year it just means even more.

The Dallas Cowboys drafted Prescott in 2016 as a fourth round pick from Mississippi State. He quickly became a sensation with a breakout rookie season, winning the OROY after throwing for 3,667 yards and 23 touchdowns. He also rushed for 6 touchdowns and 282 yards on 57 carries.

In the past decade, he has broken several Cowboys records, including the franchise record for most career passing yards and most games with 3+ touchdowns. However, his postseason record is still paltry. Across five postseason appearances, Prescott has taken the Cowboys to seven games. They have only won twice, the last win being a wildcard game in 2022.

An unfortunate end to Dak Prescott’s season with CPOY loss to Christian McCaffrey

The Dallas Cowboys quarterback was named a finalist alongside Christian McCaffrey, Trevor Lawrence, Stefon Diggs, and Aidan Hutchinson for the Comeback Player of the Year. Though Prescott had a spectacular season, coming off a hamstring injury last year, he unfortunately wasn’t much of a presence like McCaffrey.

Christian McCaffrey
Christian McCaffrey (Image via San Francisco 49ers)

The San Francisco 49ers running back had an absolute hold on the votes, winning the majority of 31 first-place votes. Aidan Hutchinson came in second with nine first-place votes, while Prescott finished third with six of those.

In the 2025 season, Prescott delivered a strong performance, throwing for 4552 yards and 30 touchdowns. He led the league in most completions by a quarterback. During a point in the season, Prescott gained serious momentum as a potential MVP winner after back-to-back games leading the offense in Dallas to wins. However, despite his individual brilliance, the Cowboys could only manage a 7-9-1 finish out of the playoffs with 12th rank in the NFC.

Meanwhile, McCaffrey finished the season among the NFL’s leaders in total yards from scrimmage (2126). He also led the league with 416 touches. He played a symbolic role this season after missing most of the 2024-25 season on the sidelines due to his Achilles injury. He jelled well with Brock Purdy and Mac Jones, becoming one of the biggest reasons behind the Niners’ return to the postseason.

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