Disclosure: I am a lifelong, die hard Boston Red Sox fan.
That said, I don’t blame Jon Lester one bit. You can look at this decision from any number of angles, but any way you unpack it the answer is the same: Chicago is the best fit for Jon Lester.
While it is close, the Cubs edge the befuddled Red Sox in terms of win-now potential. In Chicago, Lester heads a mediocre-with-upside rotation that will feature Jake Arrieta (2.56 ERA, 2.26 FIP last year) and Kyle Hendricks (2.46 ERA, 1.08 WHIP) as the presumed 2 and 3 starters. Behind them is nothing but depth as Tsuyoshi Wada and Jason Hammel were above average last year, and Travis Wood and Edwin Jackson have been All-Stars (though terrible last season), and Dan Straily, Felix Dubront and Jacob Turner (just 23) have had success at the Major League level despite regressions last season. There is even some minor league starting pitching that is quite close, with Dallas Beeler debuting last season, and C.J. Edwards and Pierce Johnson tearing up Double A.
The Red Sox have no idea what’s going on. As it stands, Clay Buchholz is the Opening Day Ace, followed by Joe Kelly. After that (utterly depressing) front end, nothing is clear. In competition for the 3, 4, and 5 spots are Rubby De La Rosa (4.43 ERA), Anthony Ranaudo (4.81), Allen Webster (5.03) and Brandon Workman (5.17). Matt Barnes (3.95 AAA) could also contend with a solid Spring Training.
Offensively, Chicago is set for the next decade, but Lester will have to hope for early production from young studs if he wants real run support in 2015. Javier Baez is a generational talent but will need to adjust to Major League offspeed stuff to have success, and fans may need to wait until summer to hear from Kris Bryant (and then should still expect some adjustment period). Arismendy Alcantara and Jorge Soler showed great poise in their debuts, but the final vote is still out. Anthony Rizzo and Starlin Castro will be solid anchors once again.
If all the Boston bats could play at once, they’ll score a ton of runs. Strangely, that’s not the way it works. Manager John Farrell will be twisting his brain into pretzels to fit all these guys into the lineup–and then hoping they can catch a ball once they’re in the field. (Did I mention the pitching staff will likely be surrendering it’s share of laser beams?) The posted Red Sox depth chart is a joke and I won’t even get into the logistics here.
At the end of the day, Boston bungled the situation when they offered their Ace a contract that, as it turned out, was a year shorter and just about 1/3 lower average annual value than the contract he just signed. More than that, the Cubs have a vision and identity. The Red Sox are rudderless. If I’m Jon Lester, I choose Chicago too.
-Ari Glantz
