Just as the Dallas Cowboys began shaping their offseason around George Pickens’ breakout year, a new wrinkle has emerged that could complicate Jerry Jones’ plans to secure his rising star long-term. With Dallas now expected to lean toward the franchise tag as contract talks approach, what once looked like a smooth extension is now turning into a far more delicate and expensive situation. And yes, insiders are already warning that it won’t be easy to navigate.

“This is actually a much harder deal to do substantively than Micah Parsons,” insider Mike Tannenbaum said on NFL Live. “Micah Parsons just paid the bill, and we’re done as the best pass rusher in the league. This is harder… because if I’m George Pickens, with 1,400 yards and nine touchdowns, I want number one money. If I’m down, I’m like, Hey, let’s hit 100% of a double. Let’s give you Tee Higgins around 28-ish. That’s a big gap, and if I’m George Pickens, why am I taking a backseat to anybody?”

Higgins signed a 4-year, $115 million contract extension with the Cincinnati Bengals in March 2025, keeping him under contract through the 2028 season. The deal includes roughly $30-$41 million in guaranteed money, with a $28.75 million average annual value (APY). In 2025, Higgins had 59 catches for 846 yards and scored 11 touchdowns in 15 games in 2025.

On the other hand, in 2025, Pickens finished third in the league with 1,429 receiving yards. He also caught 93 passes and found the end zone nine times. As a result, he earned second-team All-Pro honors and his first Pro Bowl selection. Meanwhile, PFSN graded him at 88.4 in its WR Impact metric, ranking him third behind Puka Nacua and Jaxon Smith-Njigba.

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Consequently, those numbers were not empty stats. In Dallas, he drove the offense for America’s Team. He made up 32 percent of the Cowboys’ receiving yards and delivered five 100-yard games, including two in November. Not surprisingly, he now sits atop PFSN’s Top 100 pending free agents list.

That production is exactly why the Cowboys have no intention of letting Pickens test the open market. According to ESPN’s Adam Schefter, Dallas is expected to place the franchise tag on Pickens once the window opens later this month, a move projected to cost roughly $28 million for the 2026 season and serve as a placeholder for long-term negotiations.

The tag would immediately remove outside bidders from the equation, but it also underscores how far apart the sides could be on a multi-year deal, especially with Dallas already carrying major cap commitments to Dak Prescott, CeeDee Lamb, and several defensive stars.

Because of that, the Cowboys must act fast if they want to keep him off the open market. A long-term deal or the franchise tag needs a decision soon. But where does Pickens stand in all of it?

Earlier this month on DLLS Sports, he addressed the tag talk.

“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. “I just wait on them. That’s all I really do. And chill with the guys.”

Pickens has consistently made it clear he would love to remain in Dallas, but he also understands the business side of what comes next after completing his rookie contract, one that paid just $6.75 million over four seasons before his breakout year dramatically reset his market value.

So now the pressure shifts to Jerry Jones. However, a Cowboys legend recently offered blunt advice to the Pickens, a message that could shape these talks.

Michael Irvin wants George Pickens to stay in Dallas

Last week, Pro Football Hall of Fame wide receiver Michael Irvin appeared on USA Today’s Sports Seriously and made his stance clear. He wants George Pickens to understand that the Cowboys offer him the best path forward and that Dallas is where he belongs.

“I hope he is not a dummy,” Irvin said. “I know he’s not a dummy, but I hope he doesn’t let this guy, any guy, persuade him. George has been looking for an opportunity, as he got in Dallas with a team that can get him the ball, and now he has that. It’ll be ludicrous and stupid to say, ‘All right, now that I finally found it and I had my best year, I’m just going to get up and go.’”

Irvin also urged Pickens to work smart. He said the receiver should tell his agent, David Mulugheta, to push for the strongest deal possible with America’s Team while making it clear he does not want out.

Notably, Irvin shared similar advice with Micah Parsons before his exit to Green Bay. However, tension filled The Star, talks stalled, and Parsons left, leaving Jerry Jones facing backlash across Cowboy Nation.

Earlier that offseason, the Cowboys placed a huge offer in front of Parsons. Five years at around $40.5 million per season, totaling roughly $202.5 million. On paper, it screamed commitment. Still, Jones handled the meeting himself without an agent present, and that decision shifted the mood quickly.

Now, that is the real concern. The NFLPA structure exists for a reason, and direct approaches can create friction. With Pickens next in line, Jones cannot afford another misstep, or the noise inside AT&T Stadium will grow loud again.