The Pittsburgh Steelers had a tough decision on their hands last offseason with T.J. Watt. The franchise player who will go down as one of the greatest in Steelers history wanted a contract extension. However, he was coming off a season in which he had a slight dip in production, and he had just crossed the wrong side of 30 years old.

Some wanted the Steelers to trade Watt when his value was still high. Pittsburgh gave him a massive contract extension instead, something that former NFL scout John Middlekauff said they have to be second guessing.

“I love T.J. Watt. How hard he plays, everything he’s accomplished in his career. By all accounts, what he means to that locker room, his leadership, his overall presence in the franchise. But 2024 happened…Yet, the Steelers capitulated last year and gave him over $100 million guaranteed,” Middlekauff said Friday on his 3 And Out podcast. “I think the Steelers’ biggest regret, and there’s no doubt about it, if they could have a do-over, they never would have given him that big contract…Sometimes loyalty can really screw you up.”

Watt wasn’t exactly coming off a bad season in 2024 with 11.5 sacks and 19 tackles for a loss in 2024 while playing in all 17 games. Numbers most edge defenders would be very happy with those numbers, but it was a dip in production after Watt led the league with 19 sacks the year prior. That, his age, and the fact that the Steelers made him the highest-paid non-quarterback at the time all made it a little risky.

So far that risk hasn’t paid off.

Granted, Watt sustained a freak lung injury last December that broke up some late-season momentum, and he was part of a defensive scheme that gave the Steelers lots of problems last year. But in 14 games, he had just seven sacks and 10 tackles for a loss, a drop in production for the second-straight year.

Watt’s contract doesn’t expire until after the 2028 season, and he’s owed $32 million guaranteed in each of the next two years. If he can’t improve from his seven-sack campaign last year, it presents the Steelers with some obvious problems. Although some think he’d still net a first-round pick via trade, it’s hard to imagine his value is truly that high given his age and declining production.

Pittsburgh’s got a logjam on the edge now. Watt, Alex Highsmith and Nick Herbig are all under contract for the foreseeable future. Herbig extension is one Middlekauff approves of, but Watt’s contract puts Pittsburgh in a tougher spot if it ultimately wants to break that group up. Thus, Highsmith’s name is popping up in trade speculation.

On a more positive note, the Steelers still have some hope with Watt. His splash plays were still there last year. And perhaps new Steelers DC Patrick Graham will help him return to form. But for now, Middlekauff doesn’t see his contract aging well.