All the Red Sox had to do was pay Jon Lester

Greg M. Cooper-USA TODAY

By Matt Dolloff, 985TheSportsHub.com

A lot has happened in the five-plus years since the Red Sox opted to trade Jon Lester instead of paying him what he was worth. There have been massive highs, like a 2018 World Series championship, but there have also been crushing lows. And now it's fair to wonder if, had the team paid Lester in the first place, the ensuing highs would have outweighed the lows. It's been the other way around.

The Red Sox infamously offered Lester a reported lowball offer back in 2014 spring training. Their AAV was $17.5 million when the going rate at the time was closer to $20-25 million. The decision to trade him to the A's instead of giving him a contract like five years and $120 million, which Lester himself said he would have taken, set off a chain of events that led to the Sox ultimately trading Mookie Betts and David Price to the Dodgers and eating half of Price's contract in cash considerations, in exchange for two good-if-not-great prospects and a move under the luxury tax. The last part was only important to ownership so fans are rightfully angry about the move.

There's no positive way to spin this.

You may argue that the Red Sox had to make this move because Betts ultimately didn't want to stay in Boston. Because he wanted to hit free agency and explore the whole market. That may be true, but if the Red Sox didn't continually chase talent for big money they wouldn't have had to make Price and Betts the sacrificial lambs for their decisions. They could have gotten a much better return of prospects if the luxury tax wasn't such a consideration.

You may argue that the team is now going to be able to safely spend in the coming years after shipping $62 million off their payroll in 2020 and beyond. That may be true. But the odds are extremely low that they end up spending on a player who approaches the abilities of Betts. In fact if they do that, they'd be making the same mistake they're ostensibly trying to avoid with Betts, and likely with a worse player.

You may argue that they got a couple of good players in return, that chief baseball officer Chaim Bloom made a shrewd couple of acquisitions. But again, it would be hard for either outfielder Alex Verdugo or righty Brusdar Graterol to come close to making up for the loss of Betts in the lineup and in right field at Fenway Park.

Sep 16, 2018; Boston, MA, USA; Boston Red Sox right fielder Mookie Betts (50) looks at umpire Bill Miller (26) after being called out on strikes during the first inning against the New York Mets at Fenway Park. Mandatory Credit: Winslow Townson-USA TODAY Sports
Sep 16, 2018; Boston, MA, USA; Boston Red Sox right fielder Mookie Betts (50) looks at umpire Bill Miller (26) after being called out on strikes during the first inning against the New York Mets at Fenway Park. Mandatory Credit: Winslow Townson-USA TODAY Sports

Ultimately, the Red Sox put themselves in a lose-lose situation. And it happened long before they started to learn toward trading Betts in the first place.

They refused to pay Lester, who ended up signing with the Cubs for six years and $155 million - about $25.8 million per season. A year later they brought in Dave Dombrowski to be president of baseball ops, and in the ensuing winter they dropped a $31 million AAV in Price's lap. It's completely fair to note that the Price signing resulted in a World Series championship in 2018. But would a Lester signing have resulted in that? Or even better?

Before Dombrowski entered the picture, former Red Sox GM Ben Cherington dropped a combined $183 million on Pablo Sandoval and Hanley Ramirez, a pair of signings that contributed to infinitely more headaches than championships. And heading into what would become Dombrowski's final season, he chased World Series peaks from Nathan Eovaldi and Steve Pearce, both of which immediately blew up in his face in year one. Eovaldi returned from elbow surgery after the 2019 All-Star break, but ended up compiling a 5.99 ERA while splitting appearances as a reliever and starter. For $17 million.

And so here we are. Betts became too expensive for John Henry to bite the bullet and go over the luxury tax. Henry might not have wanted to spend the money regardless. And now he's paying Price, Sandoval, and Eovaldi a combined $38 million in 2020. Fans are left crossing their fingers that Chris Sale's new contract - five years, $29 million AAV - doesn't blow up in his face. All of this could have possibly been avoided if he simply paid the one guy that deserved the money.

But hey, thank the good lord Henry doesn't have to pay taxes now.

Matt Dolloff is a digital producer for 985TheSportsHub.com. Any opinions expressed do not necessarily reflect those of 98.5 The Sports Hub, Beasley Media Group, or any subsidiaries. Have a news tip, question, or comment for Matt? Follow him on Twitter @mattdolloff or email him at [email protected].