Tim Benz: Can't get optimistic about Paul Skenes contract rumors? Embrace your own cynicism first

A lot of Pirates fans and media members have been quick to dismiss this week’s “rumor” via 93.7 The Fan that the Pirates have “tried to make some headway” on a contract extension with star pitcher Paul Skenes.

Most folks have been dubious of that prospect for many reasons.

• It feels like convenient timing to leak exciting news like this to media members after the team’s debacle in Colorado and their disappointing trade deadline activities.

• Even if the Pirates opened the bank vault in an offer to Skenes, based on some of his recent comments, the franchise would also have to convince him to sign by throwing lots of additional funds at established, veteran free agent hitters.

• Whatever the Pirates are willing to offer, it’s still not going to be what Skenes will be able to command in 2030 when he gets to free agency.

• Skenes isn’t going to want to stay in Pittsburgh even if the money is fairly close to market value. He is still going to want to hit free agency as soon as possible.

Because of those reasons, I’m highly skeptical, too.

But for all of those people who are saying, “Why would Skenes ever do such a thing,” there are reasons to consider — one of which I don’t think is getting enough consideration.

Even while spending, Bob Nutting will have an eye on his bottom line.

Let’s build a hypothetical scenario where Skenes gets a mega-contract from Nutting that pays him millions of dollars more than he would make in his final pre-arbitration season next year, through his arbitration years, and what would have been a year or two into free agency.

That would extend through 2030 or 2031, when Skenes would be 28 or 29 years old. Somewhat similarly, Juan Soto’s massive $765 million contract with the Mets has a player-opt-out just after his age-30 season.

So Skenes gets a lot more money up front than he would’ve otherwise. He secures a steady, significant rate of pay through his three arbitration seasons and knows he’ll be making nine figures before 2030 or 2031.

As a comp, the Boston Red Sox just gave Roman Anthony, a 21-year-old position player, $130 million over eight years. It’s a contract that could reach $230 million based on bonuses.

But many have already wondered why the 23-year-old Skenes would ever want to do that and pitch in this baseball abyss.

His talented arm would endure at least five more years of mileage with no chance of winning. By signing any such contract, regardless of the money he makes, he’ll be delaying his parole from Pittsburgh by another year or two.

Or will he? Because Skenes and his agents are probably smart enough to know that just because Skenes will be under contract, that doesn’t mean Bob Nutting is going to want to pay it.

If Nutting pays tens of millions of dollars to Skenes — and presumably others in an attempt to win more often — and it doesn’t materialize, don’t you think he might be inclined to have his general manager (whoever that might be) trade Skenes after 2029 before the biggest chunk of the contract kicks in anyway?

Or, let’s look at it from the other side of the coin. Let’s say the Pirates do go all in and eventually recreate a three-year run of success similar to what they had in 2013-15.

Stop laughing.

Or even — gasp — win a World Series for the first time since 1979 prior to Skenes’ contract ballooning in 2030 or 2031. Mission accomplished, right? Nutting could green-light a trade for Skenes before his final year, then start the rebuild.

Hey, he tore down a winner after three years in 2015. What? You don’t believe he would’ve done that even if they had accidentally won a World Series? Who do you think you’ve been dealing with for the past 18 years?

Regardless of circumstances, the point is, just because Nutting promised the money, that doesn’t mean he’ll end up writing all the checks. Maybe somebody else will.

The Cincinnati Reds (not exactly a big market club) just willingly absorbed $36 million for Ke’Bryan Hayes. Don’t you think someone out there would absorb $35-$70 million for Paul Skenes over a year or two?

Nutting would only be “stuck” with Skenes’ money if he suffers a long-term devastating injury, or shockingly regresses. And Skenes is likely only going to be “stuck” in Pittsburgh if Nutting has a sudden change of heart and decides it’s better to lose with someone who costs a lot of money instead of just losing without him.

Otherwise, that probably means he is getting paid here, and the team has stumbled into a competitive formula as it did about a decade ago.

Again, I doubt it’ll happen. But it could be viewed as a no-lose situation for Skenes if you are just jaded enough to think that cynically of Nutting’s intentions.

I know I am. I’m not sure if Skenes and his agents are — or if they’ll even think that hard to ponder it.

Injury concerns be damned, the idea of doing nothing and betting on the Pirates to trade him after the first arbitration award might be even more appealing.

And practical.

LISTEN: Tim Benz discusses the Paul Skenes extension rumors.