Steelers Facing 2027 Crisis That Will Be Nearly Impossible To Fix

The Pittsburgh Steelers and Owner Art Rooney II made the decision to promote Omar Khan back in May of 2022 shortly after Kevin Colbert's resignation. The front office has had a very specific approach since, and that has been building up the trenches. The new regime's first crack at selecting rookies came in the 2023 NFL Draft, and it was nowhere close to being a disappointment. A variety of players were taken and have found themselves in good position roughly three years later. Highlighting the list are certainly Nick Herbig, Joey Porter Jr. and Darnell Washington, who have been phenomenal contributors.

Keeanu Benton was also part of that class and while he hasn't fully lived up to expectations, the defensive lineman has performed nicely from time to time. Overall, Khan did an excellent job when he got his first crack at things. One of the issues with drafting so well, however, is the fact that it might be very difficult to keep all of the individuals around for the long-term.

The Steelers currently are tasked with trying to extend all four players, and that's not going to be easy. It definitely helps that the team doesn't have any massive quarterback contract on the books, but there are investments elsewhere at specific positions such as edge rusher, which directly affects Herbig. It will be fascinating to see how Pittsburgh's brass navigates the situation.

During his recent mailbag, insider and team reporter Mark Kaboly was asked about the extensions that should be coming within the next couple of months. He ranked the importance of each potential one, but had some bad news for fans that enjoy watching Benton, Washington and Herbig play.

"There are not only a boatload, but very critical ones as well," Kaboly wrote. "I'll list in order of importance: Joey Porter Jr., Chris Boswell, Darnell Washington, Nick Herbig, Keeanu Benton. It’s not realistic that they will sign all five and prevent them from hitting free agency after the season, but who would be the odd players out if you can only lock up three? Benton and Herbig? Benton and Washington? It's a tough call."

The reality of the NFL is that it is nearly impossible to retain all of your successful draft picks. While four of the five listed were taken in 2023 — with Chris Boswell being the outlier — it is well within the realm of possibility for the Steelers to have to choose only a few, rather than all of them. Porter and Boswell seem like no-brainers, but it gets very tricky after that based on where money is currently spent by the franchise.

Fans will not be happy if Herbig ends up playing out his contract and landing a massive one elsewhere, but Khan has played the compensatory selection game to the best of his ability in recent years. Letting Herbig walk out the door would almost guarantee that the Steelers would be receiving a third-round pick in the 2028 NFL Draft. If he isn't extended by Week 1 of the regular season, he will almost certainly be testing the market in March of 2027.

Benton has arguably contributed the least, so it's easy to see him not getting an extension. However, he has also been serviceable and might come with a cheaper price tag, potentially even less expensive than the kicker in Boswell. For Washington, he burst onto the scene in 2025, but the new coaching regime may not see a need for someone with his services because of Pat Freiermuth being around.

Steelers Will Likely Upset The Fan Base One Way Or Another

Whether it's Washington or Herbig that ends up potentially being the odd man out, the Black and Gold faithful will not be thrilled either way. It is going to be a challenging situation to resolve, but there remains hope because of how good Khan is with the salary cap. Another thing that comes into play is the team's 12 projected selections in 2026. The progress of newcomers in the summertime could directly affect the extension decisions before the regular season.

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