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Omar Khan’s offseason spending spree has yet to pay dividends for the Steelers

Pittsburgh Steelers linebacker Nick Herbig (51) and defensive tackle Keeanu Benton (95) interact during an NFL football game, Sunday, Oct. 8, 2023, in Pittsburgh, PA. (AP Photo/Matt Durisko)

Pittsburgh Steelers linebacker Nick Herbig (51) and defensive tackle Keeanu Benton (95) interact during an NFL football game, Sunday, Oct. 8, 2023, in Pittsburgh, PA. (AP Photo/Matt Durisko)

Joey Porter Jr. watched in dismay as the Steelers kept signing other players this spring and summer. The team handed out over $300 million in contracts to five players, including three from Porter’s 2023 draft class who had not yet ascended to starter status.

The Steelers signed outside linebacker Nick Herbig, defensive lineman Keeanu Benton, tight end Darnell Washington and kicker Chris Boswell, all of whom were entering the final year of their contracts. Additionally, they acquired receiver Michael Pittman Jr. in a trade and signed him to a new deal, too.

So far, only Washington is paying early dividends. The others are struggling, making it easy to second-guess Omar Khan and the Steelers’ front office.

Much has been made of the Steelers signing backups to lucrative deals, but coach Mike McCarthy said Thursday that his staff has a plan in place for all of the newly-signed players to maximize their playing time and worth to the team.

[Cameron Heyward goes up in the air as he growls his way out of the tunnel before the Steelers game against San Francisco at Acrisure Stadium on Sunday, Sept. 10. 2023.

Cameron Heyward goes up in the air as he growls his way out of the tunnel before the Steelers game against San Francisco at Acrisure Stadium on Sunday, Sept. 10. 2023.](https://www.post-gazette.com/sports/steelers/2026/10/07/cam-heyward-emotions-on-the-sideline/stories/202610070036)

“When a player achieves a second contract, he’s earned that,” McCarthy said. “Those men put themselves in position prior to me arriving here. But yes, when you’re building your menus and putting your system together, you’re obviously looking at the veterans you have. That’s why some of those packages are in place. You prioritize them.”

Herbig signed the biggest deal at $104 million over five seasons. His numbers don’t match that monster contract. He has not registered a sack and has four solo tackles through four games.

He was asked this week to assess his play after the first month of the season.

“To be quite honest with you, not good,” Herbig said. “We’re 2-2. That’s the only thing that matters to me. I could care less about the stats and grades and whatnot. A lot of that falls on the defense. We can’t be giving up 27 points, especially against division rivals. We need to play better ball on the defensive side of things.”

Another thing being scrutinized is the new coaching staff’s distribution of playing time, with reserves getting as much as the starters at some positions.

Their four outside linebackers have played almost the same number of snaps. Herbig leads the way with 168 (all but 15 of them at outside linebacker). T.J. Watt, Alex Highsmith and Jack Sawyer have all played 160 snaps apiece.

The Steelers have 13 games remaining, and the expectation is for Herbig to produce to the level he has in the past. In his first three NFL seasons, he recorded 16 sacks and forced 10 fumbles with three recoveries.

[Steelers quarterback Aaron Rodgers talks with referees during the second half of an NFL football game against the Browns at Huntington Bank Field, Thursday, Oct. 1, 2026, in Cleveland.

Steelers quarterback Aaron Rodgers talks with referees during the second half of an NFL football game against the Browns at Huntington Bank Field, Thursday, Oct. 1, 2026, in Cleveland.](https://www.post-gazette.com/sports/steelers/2026/10/08/steelers-colts-analysis-nfl-news/stories/202610080008)

The Steelers gave Benton a five-year, $73 million contract this offseason. He is coming off his best season, when he had 5 1/2 sacks. But he’s struggled to make an impact in 2026. He also is without a sack and has just four solo tackles.

Like Herbig, Benton has been a staple in the defensive line rotation. Only Cam Heyward has played more snaps among the interior defensive linemen.

While Herbig and Benton have disappointed thus far, signing Pittman to a three-year, $59 million deal is trending toward being the worst decision of all.

Pittman has a foot injury that will now keep him out for multiple games, but even when he was healthy, he failed to fit in as the No. 2 receiver opposite DK Metcalf.

He averaged 875 receiving yards in his six seasons with the Indianapolis Colts and reached 1,000 yards twice. He scored a career-high seven touchdowns last season.

There was every expectation that he would produce similar numbers with Aaron Rodgers as his quarterback and McCarthy as the Steelers’ play-caller. But another injury in training camp forced Pittman to miss three weeks and he’s been slow to develop chemistry with Rodgers. Now he is sidelined again.

In the three games he has played for the Steelers, Pittman has seven receptions for 89 yards and no touchdowns, and he has not gotten as many looks a No. 2 receiver would typically get. Pittman ranks sixth on the team in targets.

If and when Pittman does return, there is the very real question as to whether he can live up to his sizable salary. The early returns are not encouraging.

If there was one slump the Steelers should have seen coming it was Boswell’s.

He was 13 for 20 for a career-low 65% field-goal percentage and missed five extra points in 2018, the same year he signed his first contract extension with the Steelers.

At the time, the Steelers were so displeased with Boswell’s performance that they pushed back the $2 million roster bonus he was due in March until after that preseason, in essence making him earn the bonus by making the team.

Boswell responded by making 95% of his kicks during the 2019 season and was excellent again in 2020 and 2021, leading to the Steelers signing him to a third contract before the 2022 season.

Once again, Boswell slumped, making 20 of his 28 attempts (71%) in 2022.

Boswell bounced back with a great season in 2023 and followed it up with two more, which led to his fourth and most lucrative contract this summer. The Steelers made Boswell the NFL’s second-highest-paid kicker at $7 million a season.

Now, like clockwork, he’s in the midst of another down season. He’s already missed three field goals. His latest miss, a 48-yarder last week in Cleveland, was the difference in the 27-24 loss.

When Boswell made first-team All-Pro in 2024, he missed three field goals all season.

Boswell signed in May, making him the first of the Steelers entering the final year of their contract to get a deal done.

In retrospect, the Steelers should have signed him in March and forced him to kick in the UFL so he would get all of his misses out of the way.

First Published: October 8, 2026, 12:00 p.m.

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