Why did the Red Sox trade Mookie Betts? Revisiting the failed contract talks that led to lopsided Dodgers deal

The Red Sox, who missed the playoffs, will watch Mookie Betts lead off for the Dodgers in the 2020 World Series. 

Betts was traded from the Red Sox to the Dodgers during the 2020 offseason in a widely questioned trade of one of the top players in baseball for a less-than-ideal prospect haul. Now Betts and the Dodgers are taking on the Tampa Bay Rays in the World Series, while Boston had its worst season (by winning percentage) since 1965. That contrast certainly hasn’t helped the trade’s perception age well.

There is some promise that the Red Sox will reap rewards for trading Betts in the long term. In the short term, though, it’s been all LA and Betts benefiting from the 2019-20 offseason’s blockbuster move.

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Mookie Betts trade details

Note: An initial three-team trade involving the Twins was nixed, but the Dodgers and Twins agreed to a separate deal that brought Kenta Maeda and a prospect to Minnesota while sending Brusdar Graterol, a prospect and a draft pick to L.A.

Why did the Dodgers trade for Mookie Betts?

Entering 2020, the Dodgers were coming off missing the World Series after making it but losing in both 2017 and 2018. LA began the season as seven-time defending National League West Division champions. And most of the Dodgers’ roster was intact from a season ago, when they bested the Arizona Diamondbacks by 21 games to win the division as part of a 106-56 season. 

There wasn’t doubt in anyone’s mind that the Dodgers would win the division again. But L.A. wanted to finally get over the hump and win its first World Series since 1988. Enter Betts.

Between Betts’ first full season, 2015, and 2019, he accumulated the second-most Wins Above Replacement in baseball, according to FanGraphs. The only player ahead of Betts in that span was Mike Trout. If available, Betts would be a player no one in baseball would turn down for the right price.

The Dodgers would’ve been foolish to turn down Betts in almost any deal. He’s the type of franchise-altering player that could take an already great team and turn it into world champions. As it turned out, the Red Sox wouldn’t even push L.A. too hard on the return.

According to FanGraphs, Boston got the Dodgers’ No. 5, No. 7 and No. 13 prospects in return for Betts and Price. Boston wanted to get rid of Price’s big contract, but for a team with big pockets like the Dodgers, his addition promised to help the rotation, too (before he opted out of the shortened 2020 season). That the Dodgers could get both Betts and Price without dealing any of Keibert Ruiz, Dustin May, Gavin Lux or Will Smith was a major victory for L.A. When you consider how well the Dodgers churn out top prospects, they likely didn’t lose much sleep over what they had to give up to get a top-three player in baseball.

Why did the Red Sox trade away Mookie Betts?

The first reason the Red Sox made this trade with the Dodgers has nothing to do with Betts, but rather with David Price. The Red Sox were set to owe Price $96 million over the final three years of his contract, an absurd amount of money for an aging pitcher on the decline. Reports indicate that the Dodgers agreed to pay half of Price’s remaining money, saving the Red Sox $16 million for each of 2020, 2021 and 2022. 

The part where things get tricky is justifying adding Betts as a sort of sweetner to move Price’s albatross of a contract. There had to be another way to move Price that didn’t involve moving a superstar, right?

There were a couple narratives that emerged soon following the Betts trade. Local radio station WEEI reported that Betts had turned down a 10-year, $300 million extension with the Red Sox, signalling to the team that after his contract expired at the end of 2020, he’d be testing free agency. ESPN’s Buster Olney echoed the sentiment that Betts wanted to test free agency. Betts obviously wasn’t wed to the idea of getting to free agency since he signed his huge extension with the Dodgers after being traded.

It’s also been suggested that the Red Sox moved Betts to avoid paying the Competitive Balance Tax. But it certainly would’ve been silly for the Red Sox to allow that to weigh heavily on their decision to trade Betts, because the tax would’ve equated to about $12.4 million in 2020. 

The most likely explanation is two-pronged: The Red Sox wanted to trade Betts with a season remaining on his contract rather than see him walk in free agency for nothing, and they liked the prospects they received better than the industry at large.

There’s no way of knowing for sure what was said in private between Betts and his representatives and the Red Sox. If he indicated at all that he’d likely be leaving Boston after 2020, the Red Sox would essentially be looking at a ticking time bomb. If they weren’t confident about winning in 2020, trading Betts for three solid prospects might’ve looked more appealing than seeing Betts leave in the offseason with no boost to Boston’s system. 

But in that explanation, the common criticism wondered why the Red Sox didn’t get May or Lux or Ruiz back in the deal. At least then, it looks like Boston’s betting on six years of team control of a rising star. Verdugo should be a good player, but not likely near superstar level. The same is true with Downs and Wong, who was at best the third catching prospect LA had at the time. Somewhere in Boston, the Red Sox must have felt differently. There had to have been enough combined belief in Verdugo, Downs and Wong to feel trading away one MVP-caliber year of Betts would be worth it in the long run.

Boston did finish last in the AL East in 2020 with a 24-36 record. Maybe the Red Sox saw that implosion coming and knew Betts wouldn’t make enough difference to justify keeping him, instead trading him for three future pieces. It’s not a great explanation, but it’s the best there is. 

Who won the Mookie Betts trade?

One team watched the playoffs from home, while the other begins the World Series on Tuesday night. That might already be answer enough, along with Betts agreeing to play in LA for another 12 seasons (although $365 million might now be looking a bit rich to Boston during a pandemic).

It’s highly unlikely that one of the players Boston received back for Betts ever becomes a top-three player in baseball, and we likely won’t be able to fully judge this trade until a decade down the line. But the early returns heavily favor the Dodgers as the winners here, which was the consensus at the time of the trade. Sporting News gave the Red Sox a D grade and the Dodgers an A grade when the deal was announced. 

It’ll be a while before Verdugo, Downs and Wong are finished products for Boston. Verdugo hit .308 with six homers in 53 games for Boston this season. Downs and Wong likely would’ve spent the whole season at Double-A or Triple-A if the minor-league season hadn’t been canceled. Verdugo is the best shot of making Boston feel good about this trade, as he couples a cannon in right field with developing power and an ability to limit strikeouts. 

There’s a saying in baseball, though: “Flags fly forever.” The idea is that a championship pennant will always be there, no matter what happens in the future. If the Dodgers and Betts claim the 2020 World Series in the first year of what could be a 13-year partnership, L.A. will have already ensured it wasn’t the trade’s loser. The flag Betts brought the Dodgers would fly forever.

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