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The Pirates blew their chance at keeping Andrew McCutchen around forever

The Pirates had a lot of options with McCutchen. They chose the worst one.

Houston Astros v Pittsburgh Pirates Photo by Justin Berl/Getty Images

On Sept. 7, 1982, the headline on the front page of the Pittsburgh Post-Gazette read, “Champion of the city.” Pictured was Willie Stargell, wiping a tear away from his eye, at his retirement ceremony. Elsewhere in the paper, there was an article that included this anecdote:

By the time Stargell was halfway through the hugs and handshakes with the Pirates, the tears were falling faster than he could wipe them off with a towel draped around his neck.

This was all before a game against the Mets, and the traffic was so bad getting into the park that the start of the ceremonies were delayed. In the game, Stargell came up as a pinch-hitter in the eighth inning, lined a single to center, and came out for a pinch-runner as the crowd roared and roared.

This is an article about Andrew McCutchen, by the way.

If you want the gooey stuff about the Pirates and McCutchen, I wrote about it last year, when he was supposed to be traded to the Nationals.

This is a team that waited 20 years for anything to cheer, enjoyed three years of postseason hopes, and are right back to the old paradigm, with one of the most popular players in franchise history almost certain to leave. Because that’s how it works when your team doesn’t command a market of six million people.

It’s narratively sublime that the Pirates didn’t finish over .500 from Barry Bonds to Andrew McCutchen. It’s a neat, perfect bookend that’s almost too easy to be real. One superstar left, and the Pirates were the butt of baseball’s on-camera practical jokes. Then another superstar came, and they were great. It’s almost like the 20 years in between didn’t happen. McCutchen brought them back to relevance, and he happened to be one of the most affable players in the history of a franchise that also employed Stargell and Roberto Clemente. The Pirates and their fans had earned this player like few other teams had earned their superstar.

Still, when those trade rumors came up last year, they made sense. McCutchen’s previous season was a dud, and there was some strategy to a trade. If he had really fallen into a talent vortex from which he would not escape, last season was the Pirates’ best chance to nab top prospects and save millions. Even though his season was disappointing, there were still enough teams hoping he would reclaim his MVP form that there would be something of a bidding war.

But a deal couldn’t be reached for unspecified reasons, and McCutchen stuck with the Pirates. After going 0-for-5 on May 23, nearly two months into the season, his average fell to .200. His on-base percentage was .279, and his defense was slipping. This looked like the end, and it looked like the Pirates missed their chance to recycle McCutchen’s promise into shiny new prospects.

The Mendoza Line would not claim him, though. After that game, McCutchen hit .313/.400/.540, with 22 homers for the rest of the season. While he wasn’t zipping around the outfield in the same fashion, he was dominating at the plate, finding his eye and his ability to make hard contact.

The Pirates stunk last year, but at least they had their superstar back. If you wanted to squint, you could almost argue that his 14-month dip was advantageous for them because it meant that McCutchen might settle for reasonable extension instead of a perennial-MVP-and-future-Hall-of-Famer extension. The Pirates couldn’t do the latter, but maybe they could do the former? For a special player like McCutchen?

He would have been open to the idea. I would guess that a fella that names his kid “Steel” might have some sort of connection to Pittsburgh, but that’s just me.

There was a window to keep McCutchen, one of the best human beings in the game, in the franchise for the rest of his career or close to it. It might be getting ahead of ourselves to put him in the same tier as Stargell or Tony Gwynn, but can’t be more than a half-tier below them. There aren’t a lot of players who deserve consideration for legacy end-your-career-here contracts, but McCutchen was one of them. Here was the Pirates’ chance.

They absolutely whiffed. They chose the worst of the possible options.

Option #1 - Sign McCutchen to a long-term deal

On Sept. 7, 2025, the headline on the front page of the Pittsburgh Post-Gazette would read, “Champion of the city.” Pictured would be McCutchen, wiping a tear away from his eye, at his retirement ceremony.

The only unbelievable part of this scenario is that the world is still here by 2025, but other than that, it rings true. There’s a chance in this timeline that McCutchen stumbles again and gives the Pirates five or six poor seasons that are marred by injuries, while he commands a salary that helps them afford players who can actually help the team.

Reminder: The largest free-agent deal for an outside player in team history is still Russell Martin, who signed a two-year, $17 million contract. Pretty sure a McCutchen extension wasn’t going to keep them from signing free agents. They were already going to do that on their own.

The extension might have have resulted in a championship. It might not have even resulted in a division title or a wild card appearance. But it would have brought warm fuzzies to a franchise that was used to not enjoying warm fuzzies. Their fuzzies were usually cold and unforgiving, and they had fangs as long as your arm.

Here was a chance, though. Here was a chance to make McCutchen a story of Pittsburgh baseball that didn’t have a gut punch in the third act.

If you aren’t one for warm fuzzies, well, I guess there’s ...

Option #2 — Trade McCutchen last year, when teams were thinking they could buy low

I don’t know what deals were offered. I’m not sure if the financial obligations and McCutchen’s disappointing 2016 season left the Pirates without a reasonable offer. But even if they couldn’t get top prospects back, there was an explanation. “We loved McCutchen,” it went, “but you watched last season. He was clearly on the decline. This isn’t a team that can afford to sign declining players in their 30s, so as much as we loved him, this was the only appropriate decision for us to make.”

The fans would have hated it, but it didn’t smell like an owner trying to keep payroll down, at least. McCutchen didn’t play like someone who would deserve a long-term deal at the end of his contract, even for the fanbase that loved him unconditionally. Getting prospects back then — when the Pirates still had designs on a contending season, mind you — would have seemed like a logical, practical decision.

It wouldn’t have seemed cheap, and the pain would have been fleeting.

Unlike ...

Option #3 — Make sure McCutchen has a renaissance season, then trade him for unheralded young players

Easily the worst of the scenarios, just an absolute stinker. In this one, Pirates fans get to remember how much fun McCutchen is, and how they wish he could be around forever. And then they trade him for a reliever and a tweener outfield prospect to save $12 million.

Kyle Crick is a reliever with promise. He’s a former first-round pick with a first-round arm, and he resurrected his career last year with the Giants, thriving in the majors. At no point, though, will Pirates fans be talking about Crick to their children and grandchildren. The odds of a reliever making that sort of impact are unspeakably low.

Bryan Reynolds is a switch-hitting speedster of moderate promise. He’s a former second-round pick with a first-round skill set, and while he struck out a lot at High-A, and he wasn’t especially young for his level, there’s a small chance that he will be an excellent, Shane Victorino-like piece for a team one day.


And that can be a beautiful thing. But the odds are that Crick will pitch a few years, have some ups and downs, then leave. The odds are that Reynolds doesn’t even come close to Nate McLouth levels of fame and adulation in Pittsburgh. This is what replaced the idea of McCutchen wiping tears away at a retirement ceremony.

It would have been preferable to go with ...

Option #4 — Let McCutchen walk in free agency

In this scenario, the Pirates are still cheap, but there’s sense that at least they tried. Hey, can’t blame a guy for looking elsewhere. He’s a person with thoughts and feelings. He has agency — it’s right there in the name, “free agency.” Maybe McCutchen hits well enough to deserve the qualifying offer, and maybe he doesn’t.

There might not have been a tearful retirement ceremony, but there could have been one last standing ovation, just in case he left as a free agent. That’s better than him disappearing in the middle of the offseason.

The Pirates could have kept him around indefinitely. They didn’t.

They could have traded him when it looked like there was something wrong with him. They didn’t.

They could have let him leave of his own accord, putting some of the decision on his shoulders. They didn’t.

Instead, the Pirates traded McCutchen for a two-part package of potentially useful players, not potential stars. They might have received more than they would have if he received the qualifying offer, but it’s close enough to wonder what the real risks were with keeping him one more season. It’s close enough to contemplate the harm that comes with a franchise loudly announcing that there will be no tearful Stargell ceremonies again, no player worth keeping around just because he’s a part of the team’s DNA and always will be.

The Pirates chose the worst of their options, and they timed it horribly. If we’re back here in five years, and Crick is an all-star closer and Reynolds is a star, feel free to laugh at how overwrought this is. But there won’t be a tearful retirement ceremony for a homegrown superstar, and those chances sure don’t come up an awful lot. It might be five years until the franchise gets that kind of player again, or it might be five decades.

The Pirates might not blow that chance. But they sure blew this one. And it’ll probably be a long, long wait until that next chance comes around.