The Pittsburgh Steelers are quite the conundrum, aren’t they? It’s a team that seems to have tons of needs every offseason. Yet, at the same time, the front office always seems so desperate to retain as many players on the roster as possible.

You know, all those great rosters that have won so many playoff games over the past six years.

If you lost count, that number is zero, by the way.

This year’s Steelers squad sums up that push and pull just as well as some other recent editions have — especially if you heard general manager Omar Khan speak at the NFL Combine on Tuesday.

The team seems destined to extend the contract of outside linebacker Alex Highsmith: “You know our history. When we have a young, up-and-coming player, we don’t like to let those guys go.”

He seems keen on retaining free-agent cornerback Cameron Sutton: “We love and think very highly of Cam. Conversations (on an extension) have commenced, and we will see where it goes. Just like all our other free agents, everything is on the table.”

And Khan announced that he wants to hold on to Mitch Trubisky as Kenny Pickett’s backup quarterback. And not just for this year. Khan would like him to stay beyond 2023 as well.

“Mitch has been great. He’s been great to have around, and I am looking forward to having him around — not only this year but for a long time,” Khan said.

For similar reasons as those, the Steelers decided to extend wide receiver Diontae Johnson before last season for $36 million. Tackle Chuks Okorafor got $29 million over three years. Safety Terrell Edmunds hit free agency and came back.

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To say nothing of the $136.25 million in guarantees granted to T.J. Watt, Minkah Fitzpatrick and Cameron Heyward in recent years.

Not that any of those players are bad. Aside from Trubisky, they are all starters. They are all somewhere between serviceable contributors and All-Pros. It’s hard to label any signing as a bad one, even if you might feel Okorafor and Johnson are overpaid.

Considering their lack of depth at both positions, imagine how desperate Khan and Kevin Colbert would’ve been to sign either of them if Johnson had gotten to free agency this year or Okorafor had done so last year.

That said, the Steelers still need:

• At least one starter at inside linebacker

• At least one starting-capable corner — even if Sutton stays

• A third receiver

• A primary backup outside linebacker to spell Watt and Highsmith

• Perhaps a starting defensive lineman to replace free agents Larry Ogunjobi, Tyson Alualu and Chris Wormley

• An upgrade at offensive tackle for at least depth purposes, if not atop the depth chart

It’s going to be hard to retain/extend all of those current players and expect all of those other holes to be addressed with draft choices that can play right away. Some money is going to have to be left to spend in free agency on quality players from other teams.

I know it’s not the preferred “Steelers way,” but it’s something that has to be done. Something else that hasn’t been part of the “Steelers way” lately has been making a run in the playoffs.

When the Steelers did acquire players from other teams last year, for the most part, they worked out. Ogunjobi was better than what they had along the defensive line last year. Mason Cole and James Daniels were upgrades along the offensive line. Myles Jack was decent (when healthy) and at least a better option than anyone else they had at the inside linebacker spot from the previous year.

I bring up that compliment of the Steelers front office by way of a reminder that perhaps automatically prioritizing keeping the players currently under contract shouldn’t always be done at the expense of using free agency as a second or third resort.

In other words, is keeping Sutton for at least a projected $7.6 million a year (and I think he’ll get more) more worthwhile than spending a little extra to acquire one of the big-name free agent inside linebackers who could be hitting the market?

Sure, Highsmith would be a wise extension. He’s a good complement to Watt. What if he asks for top-dollar edge rusher value, though? Spotrac lists 13 edge rushers making more than $17 million per year. Is Highsmith worth that?

Spotrac values Highsmith at $13.9 million per year. I’m willing to bet he asks for more than that. Should the Steelers just pay it because … well … he’s here already?

Same thing for Trubisky. Is he worth keeping at a $10.6 million cap hit just because of one year of familiarity? Or do you move him, absorb the $2.6 million dead cap charge he’d carry, sign another veteran QB for about $5 million and use the additional $3 million elsewhere?

If that other veteran is a guy like Jacoby Brissett, I would.

“If there’s the opportunity to improve our team with someone, we can make things happen and sign. There’s nothing that’s going to be holding us back,” Khan said of the team’s salary cap situation regarding unrestricted free agents. “If the opportunity is there, if we want to sign someone, we have the opportunity to sign them.”

Good. Let’s hope so. Let’s hope Khan still feels that way if he ends up giving some of the current Steelers close to what they want in terms of new deals.

I get it. Khan and head coach Mike Tomlin are in a tough spot. The temptation is there to retain as many guys as possible because so many other vacancies currently exist. Why let a capable player you like walk away, right? Especially when acquiring guys from other teams has been a spotty proposition in recent years.

For all the positives I pointed out above, you could come back at me with a Joe Schobert, Melvin Ingram and Malik Reed. None of them worked out so well.

It’s the “a bird in the hand is worth $10.6 million in the bush” theory, I guess.

I just wonder if Tomlin and Khan ask themselves if they are reinvesting too much in a team that hasn’t managed a playoff win since 2016.

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