What a contract year with Red Sox might have looked like for Mookie Betts

Rob Bradford
September 02, 2020 - 10:35 am

"I think we blew the Jon Lester (negotiations). We blew re-signing him in spring training." -- Red Sox principal owner John Henry, February 18, 2019.

The impetus for the comment from Henry was in regard to how the Red Sox might approach Chris Sale, who was heading into his contract year. As it turned out, ownership already had a pretty good idea they were going to re-sign the then-ace, thereby proclaiming that the Lester lesson was learned. But was it?

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In case you forgot, the Red Sox low-balled Lester heading into his final season with the Red Sox, totally misreading the market and the player. (The lefty would later admit that something in the vicinity of a five-year, $120 million deal would have got it done. He ended up signing a six-year, $155 million contract with the Cubs.) Once the season started there was no counter, paving the way for the trade deadline deal for Yoenis Cespedes and the end of the Lester era in Boston.

The misstep had the Red Sox expensively spinning their wheels for the coming years, completely whiffing on a replacement in 2015 before allocating $217 million to try and solve the problem with David Price heading into 2016. And just for good measure, the front office went all-in on locking down the position they had devalued just two years before, trading for Sale.

So, why are we bringing all of this up again? Because of Mookie Betts.

If the Red Sox decided to not trade Betts in the offseason, Monday would have represented the trade deadline we got to go through the same process the team experienced with Lester six years before. What would have they gotten back? It's not a stretch to think that the Sox could have secured Alex Verdugo, even for just that final month of the season, and no certainties that Betts would re-sign with the Dodgers. But would they have reeled in Jeter Downs and Connor Wong, as well? That might have been a reach.

By waiting on Lester the Red Sox were left sifting through offers involving all minor-leaguers with one exception, Cespedes. Probably the best non-major league option at the time was Baltimore's offer of Dylan Bundy. 

But while the timing of trading Betts was certainly better than if the Red Sox would have waited until Aug. 31, the ultimate window of opportunity was leading up to the 2019 trade deadline when the Red Sox internally discussed moving on from the outfielder. (Dodgers president Andrew Friedman even called on Betts at the time.) But it was determined that the Sox were in it enough to keep the All-Star and hope the best. The best didn't happen, as the Red Sox quickly fell apart almost immediately after the deadline.

This brings us back to the Lester lesson.

We all know now the Red Sox should have put their best foot forward leading into the contract year, locking up the lefty and figuring out the rest of the roster from there. When it came to Betts same holds true. They offered him 10 years, $310 million prior to the 2019 season, with a counter of more than $400 million. That was more than a year before the ultimate trade deadline decision had to be made so the back-and-forth was somewhat understandable.

In hindsight, however, the Red Sox should have kept pushing forward with the same gusto they did when overpaying for Price. That's how important Betts ultimately was and is.

It's impossible to predict if the same 12-year, $365 million would have been agreed upon if Betts remained in Boston. But what we do know is that if the Red Sox were willing to go as high as their previous offer, then they probably valued the outfielder in the same light as the Dodgers.

The merits of keeping Betts in the organization for the 2020 season was that it gave the Red Sox more time to put their absolute best foot forward, while also not exposing him to the glorious world of Los Angeles. Remember, one of the things that worked against the Sox when trying to re-sign Lester after the 2014 season was that he had got a taste of life outside Boston for the first time and realized it wasn't all that bad. (And that was Oakland!) The same dynamic certainly gave Betts a push toward not partaking in free agency.

Betts wasn't going to make a difference for the Red Sox' lot in life this season. He doesn't pitch. But there are other what-ifs leading into this week's trade deadline which are fair to wonder about.

There are no easy answers, except one: It sure would feel a lot different if Mookie Betts was still around.