“He’s Not Going to Sign with a Loser Like the Cubs”

New York Yankees outfielder Aaron Judge is scheduled to hit free agency for the first time after this season, and he couldn’t have lined up a better walk year. So far, he’s hitting .300 / .378 / .644 / 184 wRC +, and is pacing to top his own season-high 8.8 WAR, set back in 2017. When healthy, he’s been an absolute beast at the plate, and more than capable defensively in the outfield. In short, Judge is one of the best players in baseball. Nice time to hit the market.

Prior to the season, the Yankees reportedly offered Judge an eight-year, $ 230 million deal, including 2022, so it was essentially seven years and $ 213 million for his “free agent” years. You can assume he will be looking to top that in free agency, and probably by a considerable amount.

The question with Judge is going to be the health (he’s topped 115 games just twice in his career) combined with his age (31 next season). At its extreme size, it’s not necessarily a profile you’d expect to age very well, or at least age without substantial chunks of missed time. He’ll get his monster deal, but the signing team is going to have to know that the best years are very likely to come in the first two or three, and there might be a lot of “dead money” in the back half of the deal. That’s not a lock, of course! Judge is such a great hitter (and athlete) that he might defy the aging curves and health track record. It’s just much more likely it goes the other way.

Which is a precursor way of saying (1) I am FASCINATED to follow his free agency, because the market for his services and the types of contract offers he gets could be wild and varied; and (2) unless the Cubs believe they can make a serious push in 2023/24 (sigh), Judge is not going to be a target, and certainly not ahead of the younger shortstops. Doesn’t mean I won’t follow things closely and discuss when there are Cubs-attached rumors, but I would be surprised if he’s a primary target.

The Cubs do come up as one of seven possible teams for Judge in this ESPN write-up, which makes sense in the abstract because they are a large market team (that, theoretically, should be spending a lot more money in the years ahead ( again, sigh)).

The reasons the Cubs are offered up as a good fit: Judge is a transformative bat for a team that needs one, Judge can be a focal point and star for the team in the city of Chicago, and the Cubs have very limited long-term commitments. All fair and fine, though I’d note the stuff I said previously that make me dubious that the Cubs would ball out on the kind of contract he’s going to get.

The part of the article I want to call out, though, is kind of hilarious:

The Cubs are a big-market team with a small-market payroll, and they have plenty of financial flexibility, if they want to use it.

But would Judge want the Cubs?

“He wants to win. He’s not going to sign with a loser like the Cubs are right now, ”a rival evaluator said. “I don’t see him signing up for the rebuild.”

That is a humorously-phrased, kinda-stingingly correct point. If the money were equal, it’s pretty hard to see Judge choosing these Cubs over a club that is more obviously set up to contend right away * AND * has a better track record of consistently competing over the length of years he’s signing up for.

Money will talk, and the Cubs / Chicago do offer a lot of really great soft factors. But we can’t pretend like a player of Judge’s stature is going to sign up for a really uncertain competitive future unless he gets blown away by the money (see, for example, the Rangers and Corey Seager / Marcus Semien). That’s when it gets really debatable whether that would even be a good move by the Cubs in the first place.

So take this as yet another reason that a large market team going through cycles of “build up, tear down, deep rebuild” can be harmful in peripheral ways.

Maybe the Cubs can get around it when it comes time to convince top free agents – Judge or not – to sign up for a multi-year deal. They got Marcus Stroman and Seiya Suzuki to sign, after all. But that was before 2022 cratered, before the messaging started to shift toward what sounds like a longer-term rebuild, and before a whole lot of questions about various key players for 2023 have either been answered negatively or are still TBD.

Again, I want to be clear: the right contract offer is the primary factor in any player’s free agency. But sometimes the situation is a couple clubs are willing to go to roughly the same range, so the player has to decide on many other factors. Usually chief among those? “Do I expect to be winning over the life of this deal?”

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