How Jon Lester situation impacted trading of Mookie Betts


Some bad decisions leave permanent scars and like that regrettable tattoo many of us may have from our youth, the Red Sox should be riddled with regrets on this one.

Mookie Betts, arguably one of the greatest and certainly most dynamic players that the Red Sox have ever produced, is gone.

Regrets, the Red Sox should have more than a few…

Here’s my timeline on why the Betts trade happened -- the process started six years ago.

Winter of 2014: The Red Sox make an embarrassingly low-ball offer to a proven Jon Lester of four years and $70 million. He was traded out of town on July 31 of that year. To show what a farce that offer was, here’s a solid comparison of the value of a top end starter at the time. Cole Hamels had just signed with the Philadelphia Phillies for 6 years / $144 million. Was Cole Hamels worth twice as much as Jon Lester? Hard no.

Sadly, at the time there were plenty of rumors circling that Lester would take a hometown discount to stay in Boston. The Red Sox took the literal meaning of that one. Perhaps a starting offer of five years $105 or $110 million would’ve been a more reasonable anchor to set. That likely would have landed him for less than the six-year, $155 million he eventually agreed to with the Chicago Cubs later.

Sounds like quite a bargain now, but it gets worse. After this debacle, the real madness ensued…

Fall of 2014: Panic stricken on the heels of a lost 2014 season and a failed Lester negotiation, the Red Sox sign Pablo “The Hut” Sandoval for five years and $95 million and Hanley Ramirez for four years and $88 million. These contracts still logjam their payroll today.

Winter of 2015: Realizing the err of their ways with the Lester "negotiations" the Red Sox wildly overpay for David Price with a commitment of seven years and $217 million.

Winter of 2018-19: Following a World Series Championship (thank you), the Red Sox got sentimental and committed another $68 million over four years to the sometimes dazzling yet injury prone Nathan Eovaldi. Then in March of 2019, the oft brilliant yet chronically injured Chris Sale was extended for five years and $145 million. This contract was seemingly offered based past performance, considering the recent and obvious injury history with Sale’s ailing left shoulder.

The rest is history.

Victims of their surprising World Series success in 2013, the Red Sox leadership read and reveled in their well-documented frugal team building strategy of the year prior. They read and enjoyed their press clippings and the series of events that followed bit them back. Hard.

Had they not made such a hard line and frankly market blind offer to Lester that offseason, some of these moves that have fiscally handcuffed them since, may never have happened at all. The result of their most cavalier, know-it-all attitude during the 2014 offseason, led to the fiscal recklessness of the years that followed. The result of that fiscal madness is the unfortunate and inevitable loss of Betts, a player who should have minimally played in Boston through his prime years, which are about to come right now.

In terms of the actual trade that Chaim Bloom made for Betts, it’s about as good as you can hope for. Two highly regarded prospects and the unburdening of the albatross that was the remainder of the David Price contract is a win.

However, it’s a win in a game that the Red Sox should never have had to play in had they handled their business better in the years leading into today.