Mookie Betts has bet on himself throughout his career and been richly rewarded for it.
Then COVID-19 happened.
When the Red Sox traded Betts to the Dodgers this winter, it was because they knew they couldn't afford the impending free agent. He had already turned down a long-term offer of roughly $300 million, pegging his worth at closer to $400 million.
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After six years of contract tenders and arbitration raises, Betts found himself only months away from free agency and a haul virtually guaranteed to make him baseball's second-highest-paid player behind Mike Trout of the Angels.
Now there's a pandemic and all bets are off, leading to a difficult question: what will Betts' market be this winter?
Hall of Fame writer Peter Gammons has already posited that Betts will be lucky to make $250 million, but in conversations with league executives, even that number feels high. The dual whammy of the pandemic and looming CBA negotiations suggests this coming winter will be a free agent wasteland.
"The landscape has completely changed," said one AL executive. "No one knows what it's going to look like."
Considering the premium ownership has placed on reining in salaries while stadiums remain empty, it's easy to envision a winter where money is scarce and even superstars like Betts are forced to play on short-term deals in the hopes of scoring a better long-term contract once the game's finances stabilize.
Unfortunately, with a second wave of virus potentially hitting this fall and a vaccine nowhere in sight, the current economic conditions could remain in place for 2021 and beyond.
Every action baseball's owners have taken during the negotiation to start the 2020 season has focused on limiting player pay. Their first handful of proposals capped salaries at 35 percent of original pay, and about a quarter of the league's owners were reportedly in favor of canceling the season rather than paying the players anything.
To think that this same group would then turn around and open their checkbooks this winter defies common sense.
So where does that leave Betts? The odds of him returning to the Red Sox are low, because his former team is trying to clear payroll to begin a messy rebuild and has already decided it couldn't afford him once. Even if his price came down to $250 million, he'd be more likely to take that money in Los Angeles than Boston.
Call it the Jon Lester Principle — trading a player during a contract dispute decreases the odds of a return.
Because so few teams could afford Betts to begin with, his best bet might be staying in Los Angeles. If it's a long-term deal, it won't be for the Trout-Manny Machado-Bryce Harper money that Betts would've command in normal times. He could effectively extend arbitration by playing for one year and $30 million, but that puts him back into free agency in 2021 a year older (28) and thus a year less desirable for a long-term extension.
Making matters worse, the 2021 season is the last under the current CBA, and if the past three months have been any indication, getting the players and owners to agree on the day of the week, let alone how to divide billions in revenue, is a recipe for a work stoppage.
That means Betts might not reach true free agency until 2023, at which point he'll be entering his age-30 season, when his earning power will be considerably decreased.
That's nothing like the scenario he envisioned when he repeatedly declined long-term offers from the Red Sox in order to secure nearly $60 million in arbitration decisions.
What once looked like the offseason of Mookie may end up becoming the winter of his discontent.