Boston Red Sox

Sep 29, 2019; Boston, MA, USA; Boston Red Sox right fielder Mookie Betts (50) rounds second base to score the game winning run on a hit by third baseman Rafael Devers (not pictured) against the Baltimore Orioles during the ninth inning at Fenway Park. Mandatory Credit: Paul Rutherford-USA TODAY Sports

By Tony Massarotti, 98.5 The Sports Hub

Mookie Betts wants Mike Trout money, plain and simple, and he always has. And Trout’s most recent contract with the Los Angeles Angels pays him an annual average of more than $35 million through 2031, which is almost four presidential elections away.

Would you pay him? I wouldn’t. Not that much. Not for that long.

There are a million layers to this story, as we all know, because the idea that Mookie Betts would leave the Red Sox after this season has been out there for some time now. The Red Sox have lagged woefully in their offers to him. Betts has really given no indication he wants to sign early anyway. The Red Sox have been a year behind in most every offer while Betts has sought a contract that would effectively make him the second-highest-paid player in the game – behind only Trout by what amounts to relative pocket change.

Pretty bold of Mookie don’t you think? (He’s not that close to Trout.) And pretty laughable of the Red Sox, right?

Neither side looks good in this, which is usually what happens in a breakup.

Sep 23, 2019; St. Petersburg, FL, USA; Boston Red Sox right fielder Mookie Betts (50) on deck to bat during the second inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

Sep 23, 2019; St. Petersburg, FL, USA; Boston Red Sox right fielder Mookie Betts (50) on deck to bat during the second inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

All of that said, let’s not ignore how the Sox put themselves in this dilemma. They overspent. They underdeveloped. By a lot. They have no real trade assets because they lack prospects and have no financial flexibility, which is why they need the San Diego Padres to eat money so that they can give San Diego one of the most complete players in the game.

Think about that for a second.

At the end of the day, here’s where the Red Sox are: to get fair compensation for Betts if he were to leave via free agency after the season, they have to get under the $208 million luxury tax threshold. At the moment, the only tradeable, high-salaried player they have is Betts. The Sox are damned if they do and damned if they don’t.

There are no good solutions here.

Trade the player. Get what you can for him. Hope the pitching is healthy. And see how it goes.

You can hear Tony Massarotti weekdays from 2-6 p.m. EST on the Felger & Massarotti program. Follow him on Twitter @TonyMassarotti.

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