History has a funny way of repeating itself every year at The Star. Jerry Jones, owner and general manager of the Dallas Cowboys, might be gambling with another contract firestorm that could rival last summer’s Micah Parsons debacle. Only this time, it will be the offense that could take a big hit with a George Pickens holdout.

“Pickens has stated he would like to remain in Dallas,” writes ESPN’s Todd Archer. “But to get to a long-term deal, the franchise tag is the first vehicle to do so. At the very least, it guarantees Pickens will be a Cowboy through 2026, although it opens up the possibility of him not taking part in the offseason program, minicamp and/or training camp.”

When Dallas acquired Pickens from the Pittsburgh Steelers last season, the blueprint seemed simple. Pair him with star receiver CeeDee Lamb, help him develop, and then lock him down long-term.

The mission’s accomplished on the first two. Pickens has torched defenses for 1,429 yards and 9 touchdowns, earning second-team All-Pro honors while filling the void when Lamb battled injuries. But now comes the hard part: keeping him in Dallas without igniting another contract war.

The franchise tag window opens February 17, and Archer reports that Dallas plans to use it on Pickens, projected at roughly $28 million. On paper, it’s a smart placeholder. But in reality, it’s not that simple, especially given what unfolded with Parsons last season.

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Last summer, Jones offered Parsons a five-year, $202.5 million deal and then tried negotiating directly without an agent. That meeting turned toxic, and Parsons demanded a trade in early August.

He reportedly sat out training camp in Oxnard, and by late August, he was shipped off to the Green Bay Packers for two first-rounders. The All-Pro edge rusher signed a four-year, $188 million contract with the Packers and became the highest-paid non-quarterback in NFL history at $47 million annually.

Now, both Parsons and Pickens are represented by David Mulugheta of Athletes First, the same agent that JJ tried to sidestep last season. Meanwhile, both players have emerged as cornerstone talents deserving top-dollar deals. Moreover, both have personalities that don’t fold under pressure.

Looking back at those negotiations, if Jones fumbles these negotiations as he did with Parsons, another media circus could unfold.

But that would work in favor of the Cowboys. Jones had himself referenced the Cowboys being a “soap opera 365 days a year” before Netflix’s America’s Team: The Gambler and His Cowboys premiered last August. Another high-value contract standoff would feed that narrative perfectly.

Without Pickens, franchise quarterback Dak Prescott loses a major target, and the passing offense that ranked 2nd in the league (per FOX rankings) regresses.

A holdout could mean no OTAs, no minicamp, and no training camp: exactly what Dez Bryant threatened back in 2015 when Dallas franchise-tagged him. Bryant eventually signed a five-year, $70 million extension.

Unlike Bryant or the Parsons mess, nobody’s drawing lines in the sand just yet. Both sides are saying the right things, and the tone feels cooperative, not combative. And that matters a lot.

Jerry Jones and George Pickens seek common ground

Despite the obvious landmines around Pickens’ contract, there’s plenty of optimism around. When asked if Dallas could meet Pickens’ market value, Jones’ response was quite positive.

“Absolutely,” Jerry noted. “A lot of the reasons I did some of the things that I did last year were to retain some players that, if it had gone in different directions, I couldn’t have done it.”

The franchise tag deadline hits March 3, and the negotiations could easily stretch through mid-July. Meanwhile, Packers quarterback Jordan Love and Parsons have also tried to actively recruit Pickens during Pro Bowl week. Jones simply cannot afford another Parsons situation. And Pickens? He isn’t sweating the tag.

“I ain’t even thought about that because it’s been so much, kind of like you said, like his money and some of the space that he had,” Pickens said per DLLS Sports recently. “I just wait on them. That’s all I really do. And chill with the guys.”

Jerry Jones could also be looking at changing the way he operates the Dallas Cowboys. His latest comments, per the Dallas Morning News, have suggested as much.

“When you’re set up the way I am, that old mirror, that self-evaluation really is appropriate and has to be done,” Jerry noted. “My way of things doesn’t work if I don’t change. [If] I’m not successful, then I haven’t [changed]. There’s no other way.”

For now, the window opens with plenty of optimism. Jones learned hard lessons from Parsons and all the holdouts that came before. If he applies them here, George Pickens stays in Dallas. If not? Green Bay’s got the recruiting pitch ready.