As the Dallas Cowboys approach the 2024 season perhaps the biggest storyline is the looming Dak Prescott contract extension. Jerry Jones and company have a huge decision to make soon, as the Cowboys quarterback enters the final year of his deal. However, while the local and national media and Cowboys fans everywhere fret about whether to not Prescott will be in Big D after this season, the QB himself says he’s not worried about it.

“I don’t play for money. Never have never cared for it, to be honest with you, yeah,” Prescott said, per ESPN, after the Cowboys’ OTAs on Wednesday. “Would give it up just to play this game. So, I allow that to the business people to say what it’s worth, what they’re supposed to give a quarterback of my play, a person of my play, a leader of my play. For me, it’s about, as I said, control what I can control and handle that part and the rest will take care of itself.”

What Prescott can control is his play on the field, and that was excellent last season.

Prescott led the league in completions (410) and passing touchdowns (36) while throwing for 4,516 yards and just nine interceptions. This performance led to a 12-5 record and an NFC East crown for the ‘Boys. It also meant Prescott made his third Pro Bowl, second-team All-Pro, and was second in NFL MVP voting to Lamae Jackson.

After all that, though, Dallas once again disappointed in the playoffs, shockingly losing their opener at home to the Green Bay Packers.

And therein lies the rub for Prescott and the Cowboys. As good as he and the team are in the regular season, playoff success always seems to elude them. Now, this isn’t all Prescott’s fault by any means. Jones, Mike McCarthy, and a plethora of Cowboys players deserve blame as well. Still, Prescott’s playoff record of 2-5 speaks for itself and makes it seem like a Cowboys Super Bowl run led by the QB may never come.

Jerry Jones and the Dallas Cowboys do things a certain way, for better or worse, and with the handling of the Dak Prescott contract extension, it was again on the “worse” side.

The truth of the matter in the NFL is this: When you give a top 10(ish) quarterback an extension, they are going to become the highest or near the highest-paid player in the league and reset the market. That’s just how it works these days and that’s not going to change.

So, paying your quarterback before the rest of the QBs waiting for an extension get their bag makes a lot of sense. That’s not how the Cowboys operate, though.

With the first Dak Prescott contract extension, the team let his rookie deal run out, franchised him, and then franchised him again before coming to an agreement ahead of playing on that second tag. That delay meant the team had to pay Prescott $40 million a year instead of the approximately $30 million they would have had to if they had done the deal two seasons earlier.

This year, the same is true.

If the Cowboys did a Dak extension last offseason, they probably could have gotten away with $45-$48 million. Now, if Prescott has another excellent season and Dallas wants to keep him, they may be looking at the neighborhood of $60 million per.

This is simply bad business by the Cowboys and one of several reasons the franchise hasn’t sniffed the Super Bowl since their dynastic run in the 1990s.