Not only do the Pittsburgh Pirates roster Paul Skenes, the best pitcher in the National League, but there's a good chance that their Opening Day roster will include Konnor Griffin, one of the best prospects we've seen in years. At just 19 years old, Griffin has displayed the makings of being a true five-tool superstar that, alongside Skenes, could lead Pittsburgh to glory.
Griffin has the potential to be such an impactful player that the Pirates should consider extending him before he's even stepped foot onto a big-league field. While risky, this could be the Pirates' only chance to extend Griffin, given how their ownership operates. But what would it take to get Griffin to sign on the dotted line and sign away at least some years of free agency? Here's what an extension would look like.
What a Konnor Griffin extension would look like right now
The terms of this deal would be quite simple: a ten-year, $130 million pact in which every cent is guaranteed Griffin's way and the young phenom would have an opt-out after the eighth year. Here's how I arrived at that figure.
Extensions are often based on precedent, but it's extremely rare for a player to sign an extension before debuting in the Majors — for obvious reasons. I mean, even high-end prospects like Roman Anthony, Samuel Basallo and Kristian Campbell at least got their feet wet before signing their long-term deals. With that in mind, though, Jackson Chourio is a player worth looking at.
Chourio, MLB Pipeline's No. 2 prospect at the time who had yet to play an inning of big-league baseball, signed an eight-year, $82 million extension with the Milwaukee Brewers ahead of the 2024 season. The deal includes a pair of club options valued at $25 million each and some incentive bonuses as well. All in all, if Chourio hits those incentives and the options are exercised, the total deal maxes out at 10 years for $142.5 million.
Griffin is going to require more than that. Not only is he a better prospect than Chourio was at the time, but he plays a more valuable position (shortstop) and prices always go up with time. Chourio set the market, so it's only right to assume Griffin tops it. Griffin would do so in the guaranteed money department, and he'd be in control of when he'd be able to test free agency earlier than Chourio.
Why Konnor Griffin would accept this deal
Accepting this deal would ensure Griffin's spot on the Pirates' Opening Day roster, give him some nice financial security and still offer the chance to cash in on the open market at either age 27 or age 29. Where's the downside?
Sure, the total value of the deal isn't quite as strong as Chourio's when factoring in Chourio's options, but the fact that those are player options makes Griffin's deal more enticing. If Griffin is the player everyone thinks he'll be, he'll opt out after his eighth year, test the open market and receive one of the richest contracts in MLB history. If he isn't, $130 million isn't exactly anything to scoff at. He'd have control of years eight through 10, while Chourio is under Milwaukee's control for those seasons.
Ultimately, there's a reason young players are willing to accept extensions. While yes, they might be underpaid for their first couple of free agency years, ensuring they have security for the first six years while they're unproven (and often underpaid) could be more important. I mean, guys like Scott Kingery and Jon Singleton sure are happy they took extensions early once they failed to live up to the hype. There are also several players who rejected extensions and now regret it.
Why the Pirates would accept this deal
From Pittsburgh's perspective, this is a pretty penny. It'd be the richest contract in franchise history, beating out the eight-year, $106.75 million extension Bryan Reynolds signed with the club in 2023. It's certainly risky handing that out to a player who has yet to debut. But if the Pirates don't extend him now, when will they?
The Pirates believe Konnor Griffin can be the hitting version of Paul Skenes, says @Ken_Rosenthal.
— Foul Territory (@FoulTerritoryTV) February 26, 2026
"It looks like he's trending toward being their Opening Day shortstop." pic.twitter.com/xiLFFmSA64
The Pirates believe Griffin can be the hitting version of Skenes. Whether this happens remains to be seen, but if they're right, now might be their only time to strike on an extension. We already know they missed the boat on extending Skenes now that he's won a Cy Young Award and is off to one of the best starts ever by a pitcher. Do the Pirates really want the same thing to happen with Griffin?
It might not pan out, but if the Pirates think he's a future superstar, how can you not extend him, getting potentially three or four additional years of control than you otherwise would have? At an AAV of just $13 million at most, that's an absolute no-brainer.
Chourio's extension looks like it'll be an absolute bargain for Milwaukee, and if Griffin is as good as advertised, the figures outlined above could prove to be an even bigger win for Pittsburgh.
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