Star outfielder Mookie Betts has been a treasured player in the Los Angeles Dodgers clubhouse since the day the Boston Red Sox traded him off to them. Now that the free agency season is on the line again, the Red Sox are being heavily reminded of how erroneous they were to let go of one of the winningest players in their dugout.

Betts has gone on to win three Silver Sluggers and two Gold Glove awards since he left the team. That further proves that inefficiency was certainly not a factor that caused the trade. Will the Crimson Horse learn from their past mistakes going forward in the 2024 playoffs? Let’s delve into the list of lessons they could’ve possibly learned from past mistakes.

A mistake from the past: The day Boston Red Sox traded Mookie Betts

The 2018 MVP was sent off to the Dodgers on the fateful day of February 10, 2020. Mookie Betts was a part of the trade-off that also included lefty pitcher David Price and some cash favors. In lieu of them, the Red Sox received Alex Verdugo (outfielder), Jeter Downs (shortstop), and Connor Wong (catcher).

Mookie Betts trade in depth.

-Dodgers recieved: Mookie Betts, David Price & Cash

-Red Sox recieved: Alex Verdugo, Connor Wong, & Jeter Downs

-Price retired

-Wong inconsistent

-Jeter Downs DFA'd

-ALEX VERDUGO to Yankees.

Conclusion: Mookie Betts trade was a flop.

— SeahawksAreLife (@SeattleSports06) December 6, 2023

Verdugo and Downs were at the top of their games in their initial years. Their form saw a decline after the trade. If that was not reason enough for the Sox to suffer from trader’s remorse, the inability to fulfill the outfield deficiency that they had to suffer through after Betts’ departure made it concrete.

Mookie Betts signed a deal worth $365 million for a 12-year term with the Los Angeles Dodgers in his July 2020 extension deal with them. The 2018 AL MVP was instrumental in the Dodgers’ 2020 World Series win. The Reds did lower their tax threshold that year, but at what cost?

Empty Pockets: How letting go of an MVP haunted Boston 4 years later

Chief baseball officer Chaim Bloom might have made the right decision at that time by providing contracts that were comparatively shorter in terms. That did not help the team’s lineup, as displayed in their consecutive playoffs. Only two players are still a part of the BoSox roster from their 2018 championship team: Chris Sale and Rafael Devers.

Four years down the road, the Sox were still unable to see the face of a World Series title since their last win in 2018. No amount of cost cuts or prospect drafts helped them recover from the loss of the outfielder who went on to give their rival team the win of the century. Letting go of Betts was “a glaring mistake for the franchise,” as the Los Angeles Times put it.

The trade not only put a permanent stamp of no return on Betts’ projected salary of $30.41 million a year, but it also left the Red Sox stuck with a declining Verdugo and Downs for their future games.

No match for Mookie Betts: A look at Alex Verdugo and Jeter Downs’ Poor Red Sox Career

Infielder Jeter Downs’ form saw such a decline that he had to be designated for assignment back in 2022. The trade-in of him, Verdugo, and Wong was tagged as an “underwhelming return” by CBS Sports, and that’s saying something. Verdugo delivered a somewhat reasonable performance at the beginning of his Red Sox career; however, that didn’t stick for long.

Downs was always down for all-round plays, but he never could deliver a high-end performance in a single position. He reportedly suffered through two consecutive Triple-A seasons full of disappointments under the Red Sox regime. Verdugo was not any different, either.

The Boston Globe tagged his Yankees trade-off as them cleaning up a mess left behind by Bloom. Despite giving a solid performance—or at least trying to give one—year-round, Verdugo’s discipline has always been somewhat of a headache. The team reportedly benched the slugger for a late arrival at a home game. Before that, he was benched for not hustling in the playoffs. Betts, on the other hand, was having the time of his life post-trade.

To LAD: Mookie Betts, David Price
To BOS: Connor Wong, Alex Verdugo, Jeter Downs

WAS: Claims Downs off waivers from BOS

To NYY: Alex Verdugo
To BOS: RANDOM MFS 😭

WE GOT CONNOR WONG FOR MOOKIE BETTS NOOO

— Pasta Party (@PastaPartys) December 6, 2023

Former Boston alumni David Ortiz was very transparent about his disagreement with the team’s trade decisions. In his words, Betts’ play style is “off the charts, and he’s young, very mature. He’s the full package. He is the full package. I mean, you tell me. Why would you not make that move? We know it was a mistake.”

Betts went on to give mind-blowing performances in the Dodgers dugout. In an August game, he went on to clinch two homers and four RBIs, apart from the three hits scored. According to ESPN, that marked Betts’s 250th career home run. To quote them, “Mookie Betts’ 2nd HR tonight was his 51st hit in the month of August, the most by a Dodgers player in a month since the team moved to LA in 1958.”

Ex-Red Sox World Champion Mookie Betts Takes Aim at New York With Fiery Verbal Attack: “I See Trash Right There…”

It is very unlikely that the Red Sox could’ve made a worse decision than letting him go. Have they learned anything from it now that they are fully in the know?

Will the Red Sox learn from it: A perfect chance to utilize 2024 free agency

The Sox’s present CBO, Craig Breslow, has been careful in cleaning up past mistakes and making room for future prospects who can actually be useful to their lineup. The Red Sox’s decision to trade Verdugo to the Yankees in this year’s offseason free agency market was wise, to say the least. They got Nicholas Judice, Greg Weissert, and Richard Fitts in return. This marked the seventh trade between the two New York rivals in the past 50 years.

Watch This Story: Red Sox Fans Slam The Door On $520M Shohei Ohtani Deal Amidst Shocking Injury Setback In Blockbuster Free Agency

The lineup is already full of additional players like Masataka Yoshida and Ceddanne Rafaela, amongst others. Rafaela is likely to start playing in the majors next year, which will give the team more space to acquire future prospects. 

Players like pitcher Yoshinobu Yamamoto, Blake Snell, and Jordan Montgomery will be a perfect fit for the Red Sox mound, given their evident lack of a dynamic pitching lineup and a need to restore their 2018 glory. They need permanent players, and there aren’t a lot of them on the team with decades left on their hands to play through. 25-year-old Yamamoto, in particular, can turn out to be the missing puzzle piece. Should the Sox choose to go after him, will he be able to leave a Clemens-like legacy behind? Only time will tell!

Yoshinobu Yamamoto Reveals Free Agency Update, Red Sox Join Mets and Cardinals With Japanese Advantage