How the Red Sox could have avoided this Mookie Betts mess


On the surface, the Red Sox tried keeping Mookie Betts.

We know Betts was offered multiple opportunities to sign a healthy extension with the team, including as far back as the offseason leading into the 2017 season which was prior to life as an arbitration-eligible player.

"That was a really emotional time because I was like, ‘Mom, we’ve never seen this amount of money.’ She was like, ‘OK, cool. It’s a lot of money. I think we know it’s a lot of money. So let’s focus on the facts. Let’s focus on what is real and we took the emotions out of it.' The first one was definitely the hardest," Betts told in September. "At the time we had never seen anything like that."

Did the Red Sox' offer enough each step of the way? Some in the organization were surprised he turned down the 10-year, $310 million offer made last spring training, but in hindsight, there shouldn't have been too much eyebrow-raising.

Betts has dug in for a while, and once Mike Trout's deal got done all involved had a pretty good idea the lofty levels the outfielder was shooting for throughout the process.

Still, if you have a talent the organization is willing to extend $300-million-plus to than the conversation can't simply be about freeing up cash. History suggests that if the Red Sox truly want someone they will go to whatever financial levels needed to secure their services. (See David Price's $217 million deal.)

The Red Sox truly wanted to keep Betts. I believe that. But the hole they methodically dug themselves led them to this path that will likely result in West Coast Mookie.

The team insists the primary impetus behind any Betts deal wouldn't be about getting under the luxury tax threshold of $208 million. That was what a Price trade was for. But once J.D. Martinez opted into his $23 million for 2020 and the market for Price on his own (even in this market where teams were overpaying for starting pitching) dried up, using a Mookie trade to accomplish the CBT goal stated by John Henry seemed the most logical strategy.

Still, that is just a part of this story.

The failure of the Red Sox to develop players after the Andrew Benintendi/Rafael Devers/Eduardo Rodriguez wave was a killer in this conversation.

While the Red Sox clearly fell in love with the idea of what Nathan Eovaldi could be after his 2018 postseason heroics, if there was a pitcher in the system that represented the kind of hope San Diego and the Dodgers are currently dangling than you are talking a saving of $17 million in this coming season. Or maybe there isn't the desperation to ink Chris Sale when they did. That's $30 million in 2020.

But there was no semblance of help from within when it came to replenishing the starting rotation while Price and Rodriguez were riding out their contracts. 

If, as Henry said, the Red Sox had known for the past few years this discomfort with the CBT was coming than they should have also realized that -- assuming Martinez was going to stick around -- those two contracts were going to potentially facilitate this problem.

And you know what, we have evidence that they knew that exact thing. Here is Henry with in London on June 28:

"My take is that maybe it isn’t the best thing in the world to bring back the same team in its entirety every time. You don’t want to break a team down. But maybe a few changes wouldn’t hurt. But the feeling is always different after you win, apparently."

Player development also factors into this mess beyond just not finding pitching replacements. 

If the Red Sox felt there were young controllable position players on the horizon -- particularly in the outfield and at second base -- they could simply view Betts as a logical $400 million building block. Instead, they are viewing Betts as one of the last and best chances to find those controllable pieces.

Betts' ask is, and will be, the price the doing business for players viewed as Top 5 in the game. But in order for a franchise to dip its toes in those waters, they better have prepared for life once that conversation is surfaced.

When the Red Sox trade one of baseball's elite in his absolute prime, understand it could have been avoided. Think about that while trying to figure out what life after Mookie might look like.