The Art of Mismanagement: Mookie Betts Edition

How the Red Sox completely botched the Mookie Betts trade

Jim Davis

We all knew this was happening, it was simply a matter of when. When John Henry publicly stated that the team wanted to be under the collective bargaining tax for the upcoming season, it was the kiss of death. There was simply no way around it. Since the 2016 CBA, no team has surpassed the luxury tax in three straight seasons, which was what the Red Sox were on track to do prior to the mega deal. The penalties for a third straight year and beyond include a 50% tax on each dollar spend over the $208 million threshold, plus their first draft pick would fall back an additional ten spots. With a farm system looking more like a wasteland than a nursery, the team truly needed their pick to be as high as possible this year.

So no, getting under the luxury tax this year wasn’t just John Henry and the gang not wanting to spend on their baseball team, it was about much more. The Yankees and Dodgers did the exact same prior to building their current juggernauts. Getting under the tax was a necessary evil, which brings us to the Mookie Betts dilemma.

Simply put, they mismanaged a valuable asset.

The whole world knew the Red Sox needed to get under the tax, and teams took advantage of it. There was no Magic Johnson to take on the Red Sox’s inflated contracts this time. To get rid of a bloated contract like David Price or Nathan Eovaldi, the Sox were going to have to give something to make it worth their while. With no prospects to throw in, they were left with including a roster piece in any deal.

Dealing someone like Andrew Benintendi or Rafael Devers would have been bad business. Guys like that are extremely valuable not just because of their talent, but because they are cost controlled for the foreseeable future. Betts always made the most sense to deal out of the roster pieces due to his contract situation and desire to go to free agency.

Where John Henry and the rest of the Red Sox brass erred was in preparation. They knew they did not want to exceed the CBT for a third straight year, yet after the 2018 season, they gave Nathan Eovaldi a $17 million per year contract and gave Chris Sale over $30 million per year at the beginning of spring training right after a season in which he had to be shut down multiple times due to a “shoulder impingement” and was not the same guy come playoff time.

To make matters worse, at the trade deadline in the 2019 season, when the team was firmly out of the divisional race, they made no moves to attempt to cut salary, full well knowing they had to get below the $208 mark before the start of the 2020 season. If there was ever a time to maximize Mookie Bett’s value, it was at last year’s deadline. Teams would be lining up left and right offering far better returns than Alex Verdugo and Jeter Downs. Even if he still wanted to hit free agency, the extra half season of Betts likely would have enticed more teams to offer up top prospects.

Instead, the Red Sox stood pat, with no clear direction.

Doing so eliminated any leverage the Red Sox may have had with the Betts trade. The Dodgers knew they held all the cards, and acted accordingly. Chaim Bloom had no choice but to take the best offer from his former mentor in Andrew Friedman. All because of poor planning by the Red Sox front office. Had they just waited to see how Chris Sale would bounce back from his shoulder injury, or not overextended themselves for Eovaldi, perhaps Betts would still be patrolling right field at Fenway.

Instead he’ll be leading off 3,000 miles west, competing for his second World Series ring.

The Boston Red Sox, who make laughable amounts of profit each year, should never be punting on a season like they are now, but they put themselves in this position.

Poor management, poor planning, and poor spending.

That’s why Mookie Betts is in Dodger blue.

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