The Los Angeles Dodgers’ pitchers and catchers report to spring training in Arizona today, marking the start of Mookie Betts’ sixth season with the team. It also happens to be the fifth anniversary of the blockbuster trade that sent Betts from the Boston Red Sox to Los Angeles—a deal that looks even more lopsided now than it did at the time. Some even argue it was the most significant trade in North American sports until last week’s Luka Doncic/Anthony Davis swap.
Two days after Betts signed his 12-year extension with the Dodgers, Red Sox chairman Tom Werner defended the decision to move on from their star outfielder, pointing out Boston’s championship success. “When people are partying in Los Angeles, I just want to remind Los Angeles because I come from Los Angeles and I spend the winters there, that in the last 20 years, Los Angeles has won zero World Series and the Red Sox have won four,” Werner said (via MassLive.com). “I’ve got nothing to be complaining about regarding our past. We think we made the right decision at the time.”
Three months after those comments, Betts helped the Dodgers win their first World Series since 1988. Then, last fall, he captured his second ring with L.A. Meanwhile, the Red Sox have only made the postseason once since the trade, reaching the ALCS in 2021, but have finished in last place three times in the past five years—two more than the Dodgers have since moving to Los Angeles in 1958.
During his introductory press conference with the Dodgers, Betts acknowledged his love for Boston but understood the nature of the business. “I love Boston. It’s been my life for nine years. And so, I thank them for everything. I can’t ask them for anything more than what they did for me,” Betts said. “… It’s still a business. Once you understand that, you can put those emotions aside when it comes to business time.”
The trade, finalized on Feb. 11, 2020, came after years of negotiations between Betts and the Red Sox. With one year left before free agency, Boston was unwilling to meet his contract demands and chose to trade him rather than risk losing him for only a draft pick.
That Betts trade just keeps looking worse for Boston. Even at the time, it was baffling that a team as rich as the Red Sox would part with a homegrown superstar in his prime over money. Now, five years later, it’s clear Betts has cemented himself as a franchise cornerstone in L.A., while the Red Sox have floundered, finishing last in three of the last five seasons.
The most fascinating part is how Boston tried (and failed) to lock him up before he hit free agency. Arbitration battles, a renewal, a record-setting $10.5 million ruling—Betts clearly valued himself highly and was willing to bet on his talent. Looking back, it seems like he knew what was coming, and the Red Sox were never truly serious about keeping him long-term.
It’s wild to think that he’ll have played more games as a Dodger than a Red Sox player by 2026, and there’s a real chance he goes into the Hall of Fame with an L.A. cap. That trade didn’t just shift the fortunes of two teams—it helped shape the modern-day Dodgers dynasty.
What do you think? Is this the most lopsided trade of the last 20 years, or does something else top it?
That “best and final offer” must have been the 10-year, $300 million deal that Betts reportedly turned down before the 2019 season. At the time, it seemed like a massive bet on himself, but in hindsight, he played it perfectly. He ended up getting a 12-year, $365 million deal from the Dodgers, setting himself up financially for life while playing for a team that fully embraced him as a franchise icon.
The Red Sox, on the other hand, completely mismanaged the situation. If they were serious about keeping him, they should’ve locked him up earlier, before he hit arbitration and started setting records with his salaries. Once he went year to year, it became clear he was willing to test free agency, and their unwillingness to truly meet his value sealed their fate.
Also, the fact that they almost traded him to the Dodgers in the summer of 2019 is crazy. Imagine if they had pulled the trigger then, rather than in February 2020—would the return have been better? Would the Red Sox have salvaged more value instead of getting Verdugo, Downs, and Wong?
It’s wild to think that Betts’ decision to bet on himself and the Red Sox’s mishandling of the negotiations directly led to one of the most lopsided trades in baseball history. What do you think—was there ever a moment Boston could’ve actually convinced him to stay, or was he always destined to leave?
So the Red Sox never even put a $300 million offer on the table—just “almost” $100 million more than their previous $200 million offer, which means their final offer was likely around $275 million. That’s well short of what Betts eventually got from the Dodgers, and considering his production at the time, it’s clear he was never going to take it. Boston simply wasn’t willing to match the market.
What really stands out is how the Red Sox handled their payroll decisions. Instead of committing to Betts—who was the best all-around player they had developed in decades—they prioritized extensions for Chris Sale and Xander Bogaerts. While Bogaerts was a great deal for them at the time, the Sale extension was a disaster almost immediately, given his injuries.
It’s interesting how Betts always made it clear this was a business decision for him. He never played the “I want to be here forever” card unless the money was right. Compare that to someone like Rafael Devers, who was open to negotiating and eventually got his $313.5 million deal from Boston.
At the end of the day, it’s hard not to see this as a massive miscalculation by the Red Sox. They lowballed Betts, he called their bluff, and they ended up trading him for a package that, in hindsight, was underwhelming. If they had just given him a real market-value offer—say, $325-350 million—would he have stayed? Or was he set on testing free agency regardless?
The entire Betts trade saga really highlights how the Red Sox mismanaged the situation. Betts himself admitted that he thought a deal would eventually come together, which suggests he wasn’t completely set on leaving. But once Boston decided they weren’t going to pay him what he wanted, the trade became inevitable.
The Dodgers ended up with a generational player, and they didn’t even have to part with their top prospects (like Gavin Lux or Dustin May at the time). The fact that the Red Sox originally agreed to take Brusdar Graterol—only to balk at his medicals and pivot to Jeter Downs—makes it even worse in hindsight. Downs never panned out, and the trade package ended up being Verdugo, Connor Wong, and a throw-in reliever. That’s all they got for an MVP-caliber talent in his prime.
It’s wild to think about how different things could have been. If the Red Sox had just matched the Dodgers’ eventual offer (12 years, $365 million), would Betts still be in Boston? It sure sounds like he was open to it. Instead, they traded him, wasted the return, and then turned around and gave Devers a bigger contract than they ever offered Betts. What a disaster.
That whole mess with the trade falling apart over Graterol’s medicals just made the Red Sox look even worse. They already weren’t getting a great return for Betts, but then they nitpicked a reliever’s shoulder and ended up with an even weaker package. Meanwhile, Graterol has turned into a key bullpen arm for the Dodgers, helping them win a World Series in 2020.
And the Angels backing out of the Pederson-Stripling deal really changed the trajectory of things, too. Andy Pages was a throw-in at the time, but now he’s one of the Dodgers’ top prospects, possibly their Opening Day center fielder in 2025. The Angels, on the other hand, could’ve used Stripling’s innings and Pederson’s bat in 2020, a year where they desperately needed pitching.
It’s wild how much this whole sequence of events shaped multiple teams. The Red Sox ended up with almost nothing for Betts, the Dodgers won a title and kept a key prospect, and the Angels—well, they stayed the Angels.
That last statement from John Henry just sums up how much of a disaster this trade was for the Red Sox. They tried to frame it as a necessary move for the long-term health of the team, but they ended up getting almost nothing out of it.
Verdugo was solid but never a star and got traded to the Yankees before his final year of arbitration. Downs completely flamed out, got DFA’d, and is now with the Nationals. Wong has turned into a decent catcher, but not nearly enough of a return for a generational player like Betts. Meanwhile, Betts helped the Dodgers win a World Series in his first year and is still one of the best players in baseball.
And the financial reasoning doesn’t even hold up that well. The Red Sox gave Rafael Devers a $313 million extension just a few years later—so it wasn’t that they couldn’t pay Betts, they just chose not to. They could’ve built around him but decided to cut costs, and it backfired massively.
It’s crazy to look back and realize how much the Dodgers fleeced Boston. They got a franchise cornerstone, offloaded half of Price’s contract, and still kept their best prospects. And somehow, the Angels missing out on Andy Pages might have been the second-biggest mistake in that whole saga.
The extension was just the final nail in the coffin for the Red Sox in this whole saga. They tried to sell the idea that Betts wouldn’t have stayed even if they’d offered him a fair deal, but the Dodgers proved that wasn’t true. They got the trade done, offered him what he was worth, and locked him up long-term in a matter of months.
Boston lowballed him, plain and simple. Their “best and final” offer didn’t even crack $300 million, and once the Dodgers came with $365 million ($306.7M present-day value), Betts was more than happy to commit. It was never about him not wanting to stay in Boston—it was about the Red Sox refusing to pay the price for a generational talent.
From L.A.’s perspective, this was an all-time masterclass in front-office work. They traded for Betts with the assumption that they might only have him for a year, but they still made the move because they knew what he could bring to the team. Then they got him to buy in, paid him what he deserved, and secured one of the best all-around players in baseball for over a decade.
And looking at it now, the contract is aging beautifully. Betts is still a top-five player in the game, and now he’s showing his versatility by playing second base and even shortstop at a high level. Meanwhile, the Red Sox are stuck in mediocrity, still looking for a new face of the franchise years later.
That last quote from Betts really says it all—he moved on, built a life in L.A., and is thriving while the Red Sox are left trying to justify one of the most lopsided trades in modern baseball history. Boston’s front office and ownership framed it as a necessary business decision, but five years later, the only thing they got in return is an average catcher and a pitching prospect who might contribute someday.
Meanwhile, Betts has added a World Series ring, multiple Gold Gloves, and an MVP-caliber run in Los Angeles. The Dodgers didn’t just win this trade—they annihilated the Red Sox. They took on a bit of money, gave up some solid-but-not-elite prospects, and in return, they secured a franchise cornerstone for over a decade.
Boston fans have every right to still be frustrated. This wasn’t a case of a small-market team being forced to unload a star because they couldn’t afford him. The Red Sox are one of the richest franchises in baseball, and they chose to trade away a generational talent instead of paying him. The fallout from this deal is a big reason why the team has floundered since 2020, and why the fanbase has lost trust in ownership.
At this point, the Betts trade is right up there with Babe Ruth to the Yankees in terms of Red Sox blunders. Sure, it’s not quite on the same level, but the echoes are there—Boston let go of an all-time great, and the franchise has suffered for it ever since.
