It still feels weird. Even now, in early 2026, seeing Mookie Betts in Dodger blue or a secondary jersey that isn’t the classic Boston home whites just feels like a glitch in the matrix. For a generation of fans at Fenway, Mookie wasn't just a player. He was the energy. He was the "Win, Dance, Repeat" era personified.
Honestly, the trade that sent him to Los Angeles in 2020 is basically the modern-day version of the Babe Ruth sale, and I’m not even being dramatic. We are talking about a homegrown, generational talent who could do everything. He hit for power. He won Gold Gloves. He bowled perfect games in his spare time. He was the face of the franchise, and then, suddenly, he wasn't.
Why did the Red Sox actually trade Mookie?
People like to simplify this as "the Sox were cheap," but it’s a bit more tangled than that. By the end of 2019, the Red Sox were staring down a massive luxury tax bill. They had a roster bloated with heavy contracts—think David Price, Chris Sale, and Nathan Eovaldi—and they were coming off a disappointing third-place finish in the AL East.
Mookie wanted his value. Rightfully so. He had just come off a 2018 season where he won the AL MVP, a batting title, and a World Series. He reportedly turned down an extension in the neighborhood of $300 million because he believed the market was higher. He was right. He eventually got $365 million from the Dodgers.
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The Red Sox front office, led at the time by Chaim Bloom, felt backed into a corner. They didn't want to risk losing him for nothing in free agency after the 2020 season. So, they packaged him with David Price to shed salary. The return? Alex Verdugo, Jeter Downs, and Connor Wong.
Looking back from 2026, that trade looks... rough. Verdugo had some okay years but eventually landed with the Yankees (ouch). Jeter Downs is nowhere near the Big Leagues right now. Connor Wong has turned into a solid, everyday catcher, but he’s not Mookie Betts. Nobody is.
The 2018 peak: A season for the history books
If you want to understand why Boston fans are still salty, you have to look at 2018. It was the "most satisfying" year of Mookie’s career, by his own admission. He slashed .346/.438/.640. That’s video game stuff.
He became the first player in Major League history to win the MVP, Silver Slugger, Gold Glove, batting title, and World Series in the same season. You couldn't pitch to him, and you definitely couldn't hit it past him. He’d make a diving catch in the right-field corner at Fenway, pop up, and be smiling before the runner even realized he was out.
The chemistry that year was just different. You had Mookie, Jackie Bradley Jr., and Andrew Benintendi—the "Killer B's"—patrolling the outfield. It felt like the start of a dynasty. Instead, it was the peak of a mountain that the team has been sliding down ever since.
The fallout and the "Curse" talk
Is there a "Curse of Mookie"? Some fans definitely think so. Since the trade, the Red Sox have spent a lot of time in the cellar of the AL East. They’ve had three last-place finishes in the five seasons following his departure. Meanwhile, Mookie has added two more World Series rings to his collection in LA.
It’s not just about the stats on the field. It’s the message it sent to the clubhouse and the city. When you trade a guy like Mookie, you’re telling the fans that the "Competitive Balance Tax" matters more than the superstar they grew up watching.
Mookie Betts Red Sox legacy vs. the current reality
The Sox have tried to move on. They gave Rafael Devers a massive extension to prove they can keep stars. They’ve brought in guys like Alex Bregman (who had a short stint) and are currently looking at Bo Bichette to fill the void. But there’s a Mookie-sized hole in the culture of the team.
The Dodgers became the new "Evil Empire" by doing exactly what the Red Sox used to do: spending whatever it takes to win. They paired Mookie with Freddie Freeman and Shohei Ohtani. It’s an embarrassment of riches.
For Boston, the path back to the top involves a lot of "what ifs." What if they had just paid him? What if they had traded someone else to clear the cap space?
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What you can do as a fan today
If you're still mourning the loss of number 50, you aren't alone. But the 2026 Red Sox are in a different phase. They have a surplus of young outfielders like Roman Anthony and Wilyer Abreu who are actually showing a lot of promise.
Here is how to track the "Mookie impact" moving forward:
- Watch the luxury tax threshold: The Red Sox are projected to be more aggressive this year. Keep an eye on whether they finally push past the "reset" mode they've been in since 2020.
- Follow the trade returns: Connor Wong is the last man standing from the original deal. His development into a top-tier catcher is the only way the Sox salvage some pride from that swap.
- Appreciate the history: Don't let the trade ruin the 2018 memories. That team was one of the greatest to ever play in Boston, regardless of how it ended.
The Mookie Betts era in Boston was short, brilliant, and ended far too soon. It’s a case study in why sometimes the "smart" business move is actually the worst baseball move you can make. Ownership might have saved some money, but they lost the heartbeat of the city in the process.