Dak Prescott and the Dallas Cowboys are currently in the midst of what has been somewhat of a turbulent offseason for the team ahead of the upcoming 2024-25 NFL season. The offseason started in failure as the Cowboys were coming off of a blowout home loss to the Green Bay Packers in the NFL playoffs, and there were legitimate concerns after that game as to just how viable Prescott is as a quarterback for a team with championship aspirations.

Complicating matters is the fact that there is just one year left on Prescott's contract, meaning the pressure has been on the Cowboys' brass to make a decision as to whether they want to extend their star quarterback, and if so, how much they are willing to pay him. Thus far, it doesn't seem that a ton of progress has been made on that front, and one person who wants Cowboys owner Jerry Jones to pick a direction is none other than former Dallas defensive end Charles Haley, who won Super Bowl glory with the team during the 1990s.

“(Jones) kept back loading everything, so now he’s screwed,” said Haley, via the Up & Adams Show with Kay Adams, presented by FanDuel. “You know his bill came due, and he doesn't have the money to be able to do that. And so what he's going to have to do is, he's going to have to find another way around the salary cap or push a lot of older guys salary cap way back and then you don't know whether these guys are going to play one year or two years and then all of it comes due again. So he gambled a long time and now time is up. I can tell you this, trade Dak, just put him up for a trade, guess what, every team in the league will be after him. Dak is a winner, Dak is a great person, a great leader.”

Is Dak worth a huge extension?

Dallas Cowboys quarterback Dak Prescott (4) goes through a drill during practice at the Ford Center at the Star Training Facility in Frisco, Texas.
Chris Jones-USA TODAY Sports

Two things can be true at once: Dak Prescott is one of the better quarterbacks in the league that many teams would be happy to have, and he probably isn't good enough to be the quarterback on a championship-winning team unless that team is historically great in every other facet of the game.

There is a long list of proven evidence now to demonstrate that Prescott does indeed crack under the pressure of the playoff spotlight, regardless of how solid he may look in the regular season, and although the defense was just as abysmal as he was in the loss to the Packers last year, it was Prescott's performance alone in 2022-23 vs the San Francisco 49ers that spelled the Cowboys' downfall in that playoff game.

However, sometimes in sports it's better to stick with something good as opposed to letting it just vanish. The Boston Celtics made a similar decision last year with Jaylen Brown following his epic playoff flameout and were rewarded when Brown led them to a championship and won Finals MVP the following season.

In any case, the pressure is on Jerry Jones and his associates to make up their minds.