Red Sox: Former MLB GM predicts what Mookie Betts extension would cost

Mookie Betts appears unlikely to sign a contract extension with the Boston Red Sox this winter but here’s what an offer could look like.

The future of Boston Red Sox star Mookie Betts has been a hot topic with the right fielder only a year away from free agency. The narrative continues to shift between whether or not Betts can be locked up with a long-term extension or if the team will trade him to save payroll space.

Former MLB general manager Jim Bowden of The Athletic recently made a player move prediction for every team. Betts was unsurprisingly who he focused on for the Red Sox, making a case for extending their superstar to a 10-year, $370 million deal.

"“There is not going to be a Betts trade out there that’s going to tempt the Red Sox at this point,” writes Bowden. “They’ve waited too long, and anyway, their best play all along has been to extend him long term and find other ways to reduce their payroll. Betts is their best player and will get more than both Bryce Harper and Manny Machado on the open market.”"

There’s plenty to unpack from this statement so let’s break it down, starting with the most obvious – the best move the Red Sox could make is reaching an agreement with Betts on an extension that keeps him away from the open market. They can find other ways to shed salary if dipping under the luxury tax is really as important many appear to believe.

Trading Betts is a long shot at this point. As Bowden mentions, the Red Sox waited too long to explore that path. No team is going to surrender their top prospects for a one-year rental and pay the $28 million Betts is projected to earn next season. There’s zero chance of getting fair value in a trade which means the Red Sox would essentially be salary-dumping their best player for whatever they can get. That’s not happening.

The problem is that Betts is adamant about waiting for free agency in order to maximize his value so he isn’t interested in an extension. How much money would the Red Sox have to throw at Betts to get him to change his mind?

Bowden’s prediction of $370 million should certainly grab his attention. That would be the second-largest deal in MLB history, trailing only Mike Trout‘s 12-year, $430 million extension that he reached with the Los Angeles Angels last year. The $37 million average annual value of this proposed offer would top Trout’s $35.83 million.

Let’s be clear, as great as Betts is, he’s no Mike Trout. Betts has an MVP under his belt but Trout has won the award three times and finished as the runner-up on four occasions. Trout’s 72.0 WAR in his first eight full seasons puts him on a historically great trajectory. Betts has been excellent with 39.7 WAR in five full seasons but Trout is on another level.

If Betts is holding out for free agency hoping to break Trout’s record he’s going to end up disappointed. Waiting until he’s 28 years old would make him a year older than Trout was when he signed his new deal, almost certainly eliminating any chance of matching his 12-year contract. If maximizing the total value of the contract matters most to Betts then signing early makes the most sense. If the average annual value is more important then he should be satisfied with Bowden’s prediction that carries a higher AAV than any player in baseball.

As rationale as this seems, I’m not convinced that Mookie sees it this way. Bowden is correct that Betts should get more than Harper or Machado received last winter and that’s exactly why he plans on waiting.

Let’s say for example that the Red Sox offered Betts a 10-year, $300 million deal on the first day of free agency last year when he was 26 years old, the same age as Harper and Machado. At the time, that would have trailed only Giancarlo Stanton‘s 13-year, $325 million deal only with a much higher AAV. That would be hard to pass up based on the precedent set by star players who previously signed mammoth deals, right?

Except that later that offseason, Machado signed for that same amount. A few weeks later, Harper signed a record-breaking 13-year, $330 million deal (later topped by Trout). Betts would be kicking himself if he settled for $300 million knowing he’d almost certainly get more if he waited until after those two free agents signed.

There’s less risk of that happening with this year’s free-agent crop. Anthony Rendon is easily the top position player on the market but the 29-year old isn’t getting a 10+ year deal (MLB Trade Rumors predicts he’ll get 7-years for $235 million).

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That doesn’t mean Betts can’t potentially benefit by waiting. Francisco Lindor and Kris Bryant have been heavily tied to trade rumors. The Indians aren’t willing to pay up for their star shortstop but what if they trade Lindor to a team that gives him a massive extension? The Cubs could pivot toward locking up Bryant or trade him to a team that will. If those players set a new standard for what elite talent is worth then Betts can top it next year rather than being the one to set the bar.

Waiting can also backfire though. Forget the risks of injuries or a down season diminishing his value. Betts will be hard-pressed to get 10+ years if he waits until he’s 28 years old. Machado signed a deal of that length because he was two years younger than Betts will be next offseason. Harper took 13 years in order to allow the Phillies to spread the money out at a lower AAV for luxury tax purposes.

A more realistic comparison if Betts waits until next year is the 8-year, $260 million deal that Nolan Arenado received from the Colorado Rockies last offseason (he turned 28 in April). Maybe Betts gets a bit more, say 8-years, $280 million or 9-years, $315 million. That $370 million deal probably isn’t on the table from the Red Sox, or any team, for a 28-year old.

With all that in mind, here’s what’s most likely to happen. The Red Sox will do their due diligence by shopping Betts this winter. They won’t find a reasonable offer and will instead focus on finding another way to save money. Boston’s brass will certainly try to convince Betts to sign an extension and Bowden’s proposal would be a fair offer. Betts will scoff at the offer anyway, rolling the dice on his future.

Betts will wear a Red Sox uniform for the 2020 season before hitting free agency a year from now. He’ll end up cashing in with a contract that at least comes close to the record for AAV but ultimately falls short in terms of total value compared to what he’d get right now. The Red Sox will have some competition if Betts hits the open market but I believe they end up matching any offer that is remotely reasonable and he ends up staying in Boston.

Bowden has the right idea of what the Red Sox and Betts should do but I remain skeptical that it will actually happen this year.