Surviving Barstool | New Episodes Tuesday, Wednesday & Thursday 8PM ETTUNE IN

Here's Yet Another Reminder Of How Badly The Red Sox Fucked Up By Not Re-Signing Jon Lester

I love this man. While the Red Sox were once again bounced in the first round of the postseason, having won zero postseason series (and only one postseason GAME) since lowballing Jon Lester during spring training in 2014, later trading him to the Oakland A’s that July, and then making a halfhearted and lame ass attempt at re-signing him in free agency that winter, Lester is on champagne celebration number NINE with the Chicago Cubs. That’s right — nine. I counted. He’s also in pursuit of ring number two in Chicago, which, in three years, would equal his ring total over nine years in Boston.

You might remember the Red Sox randomly pulling a philosophy out of their asses that they don’t sign pitchers over the age of 30 anymore. Weird timing, since that was only their thought process during their negotiations with Lester. Oh, and the following winter, they had no problem writing a check for $217 million for, then, 30-year-old David Price. Not that I regret Boston signing Price whatsoever, because, in theory, they could’ve had both. But not re-signing Lester will go down as one of the worst mistakes in franchise history.

The Red Sox were complete assholes when they offered Lester $70 million over four years in the spring of 2014. It was an absolute slap in the face. They knew it then, but I’m sure they realize that even more now. Since Lester signed with the Cubs, the Red Sox have finished in last place in 2015, and in 2016 and 2017, six Red Sox starters (David Price, Rick Porcello, Clay Buchholz, Chris Sale, Drew Pomeranz and Doug Fister) have combined for an 0-5 record with a 10.96 ERA in seven starts in the postseason, averaging 3.1 innings per start.

Since joining the Cubs, Lester has a 2.58 ERA and a 0.91 WHIP with 49 strikeouts in 59.1 innings in the postseason. Of the 25 starters who have made at least three postseason starts since 2015, Lester ranks fourth in ERA, is tied for second in WHIP, and has thrown the most postseason innings. Red Sox starters, over the last two years, have thrown 39 innings in the postseason combined. Lester alone has thrown 45.1 innings with a 1.99 ERA. Let that sink in.

I think what I’m trying to say here is that maybe, possibly, just perhaps the Red Sox made a colossal mistake when they lowballed Lester, traded him, and then came in with yet another underwhelming offer in free agency. Don’t tell me to “get over it”, either, like it’s supposed to get any easier watching Red Sox starters shit their pants in October time and time again, while Lester sips champagne round after round.

Good for him, though. Winning in the postseason is always great, but it must feel even better knowing that each champagne celebration sticks it to those fucking morons on Yawkey Way every single time.