Welcome to Snyder’s Soapbox! Here, I pontificate about matters related to Major League Baseball on a weekly basis. Some of the topics will be pressing matters, some might seem insignificant in the grand scheme of things, and most will be somewhere in between. The good thing about this website is that it’s free, and you are allowed to click away. If you stay, you’ll get smarter, though. That’s a money-back guarantee. Let’s get to it.
Let’s examine several things that are all true.
1. The Pittsburgh Pirates have a rightfully disillusioned fan base who hates ownership. They’ve endured a 20-year streak of losing and not making the playoffs, broken up only by a brief three-year reprieve in which the team never advanced past the NLDS. They’ve had one winning record since 2015, but didn’t come close to making the playoffs that year. After back-to-back seasons of at least 100 losses, the Pirates went 76-86 in consecutive years. This year, they’re 29-44, on pace to finish 64-98.
2. Paul Skenes is off-the-charts amazing. Through the first 38 starts of his MLB career, Skenes is 15-9 (for a bad team) with a 1.89 ERA, 0.91 WHIP and 267 strikeouts in 229 innings. He’s done everything asked of him, from ridiculously short Triple-A outings last year when it was clear he should be in the MLB rotation to a workhorse’s load this season, in which he leads the National League in innings pitched. He finished third in NL Cy Young voting last year despite only making 23 starts. This year, he’s even better.
3. Paul Skenes is cheap right now. He’s making $875,000 this season. He won’t be in arbitration until 2027 and doesn’t hit free agency until after the 2029 season. Generally speaking, a good time to grab the youngest players on a long-term extension is when they aren’t making seven or eight figures a year.
4. There’s been more chatter about a Skenes trade than extension. Now, let’s be clear: None of the “should the Pirates trade Skenes” talk has come from the Pirates as far as we know. I actually think if they traded him this season it would rise nearly to the level of scandal to the point where the MLB office would need to intervene and remove ownership. Skenes was the No. 1 overall draft pick in 2023 and he’s been one of the best pitchers in baseball. Trading him when he’s not even making $1 million? Yeah, that can’t happen. And it won’t. The reason it gets brought up, though, is because it’s the Pirates and this is how they operate.
Now, if we add those four points together, it tells me that the baseball world is absolutely screaming for the Pirates to knock Skenes over with extension that he can’t refuse. Make him the franchise centerpiece. Build around him.
Have any talks happened yet? It doesn’t seem like it.
“That hasn’t happened,” Skenes told Sportico on May 29. “This is about the here and now. I’m not in any rush for a decision to be made like that. I don’t think they are, either.”
Um, yeah, Pirates? Hello? You should be in a rush here. Skenes should know you’re in a rush.
And don’t tell me it isn’t possible because of “market size.” All the Pirates fans who believe this have been beaten down by Bob Nutting and his minions for years.
Fernando Tatis Jr. is on a 14-year, $340 million extension with the Padres. The Brewers gave Ryan Braun two extensions and made him a Brewer for life. Christian Yelich right now is on a nine-year, $215 million deal in Milwaukee. Joey Votto had a 10-year, $225 million with the Reds. Bobby Witt Jr. with the Royals has a deal that could get pushed as high as 14 years and $377.7 million.
(We could discuss Wander Franco and the Rays here, too, but let’s just agree to move on.)
Could the Pirates come up with a deal that starts at 10 years and $200 million, plus bells and whistles? Easily.
The time to offer such a deal is, again, before Skenes is even making a million bucks a year. Flashing a guaranteed $200 million four years before any other team can even make an offer is a good way to get the player to agree. What if he suffers a major injury and never returns to form? It sucks to consider, but given the nature of the sport, particularly for pitchers, $200 million can be hard to say no to. It takes two to tango (and to sign an extension) but don’t you have to at least try?
On the Pirates’ end, not only does it give you cost certainty moving forward with Skenes, but you’ve hopefully won great favor with the fan base and also have a major selling point moving forward to free-agent targets — hopefully bats to add to that great pitching — in terms of being competitive. Nothing tells a player that you’re trying to win like, well, trying to win.
The Pirates’ biggest contract extension is Bryan Reynolds at eight years and $106.75 million in 2023. Ke’Bryan Hayes scored an eight-year, $70 million extension in 2022. These are still pretty light deals for being the two biggest in the franchise, but if the Pirates locked down Skenes, they could earnestly start selling to the fan base that the front office is operating differently now and the great citizens of Pittsburgh can fully embrace the organization again. And for those worried, no, Skenes’ agent isn’t Scott Boras (it’s ISE Baseball).
I guess the question is whether or not the Pirates want to operate like a Major League Baseball organization or continue to act as the team whose fans are resigned to watching Skenes win a World Series with someone else in a few years.
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