Lackey has showed no signs of slowing down as he enters his late-30s (Fox Sports)
On July 31st, 2014, Ben Cherington broke up the 2013 World Series champions by trading Jon Lester and John Lackey, among others, to the Oakland A's and St. Louis Cardinals, respectively. Sixteen months later, they have been reunited under former Sox GM Theo Epstein, the man who developed Lester and signed Lackey in Boston, with the Chicago Cubs.
Lester joined the Cubs last winter, signing for more money than any free agent besides Max Scherzer. Lackey stayed in St. Louis, earning the league minimum because of an injury clause in his contract. Both were terrific in their first full seasons as National Leaguers, pitching their respective clubs to the postseason and squaring off in Game 1 of the NLDS. Lackey got the best of Lester, allowing just two hits over 7 and 1/3 scoreless innings, but in the end it was Chicago who advanced to the NLCS (only to be mercilessly swept by the Mets).
Now, the onetime beer buddies and former division rivals are teammates once more. It was reported yesterday that Lackey and the Cubs had agreed to a two-year, $32 million deal. Lackey joins Lester and Jake Arrieta in the Windy City, giving Chicago a formidable trio at the top of its rotation. The Cubs have plenty of hitting, so they were wise to add a starter, snapping him at up at a reasonable price to boot.
While nowhere near the bargain the Cardinals got with Lackey last year, this still figures to be a pretty favorable contract for Chicago. They get a great starting pitcher at a fraction of the cost that David Price, Zack Greinke, and Jordan Zimmermann just inflicted on their new clubs. Even if Lackey's only half the pitcher he was last year, when he was worth roughly 4.7 WAR (after splitting the difference between B-R and FanGraphs) with a 2.77 ERA over 218 innings, he'll still be worth the money. And since it's only a two-year pact, the Cubs won't be stuck with him if he bombs.
Which, at his age, is a very real possibility. Lackey just turned 37 and has churned out over 2,600 innings (postseason included) on a Tommy John-repaired arm. Pitchers at his age are susceptible to losing it overnight, as we recently saw with Roy Halladay, Roy Oswalt, and others. It's hard to say how he'll fare in Wrigley Field seeing as how he's started all of two games there, but there's no question his new home is tougher on hitters than his old one (I'm not too concerned about this, however, as Lackey's not a flyball pitcher--the kind who are susceptible to Wrigley's wind--and he had success at Fenway)
Lackey's due for some regression after outpitching his FIP by 0.8 R/9 and enjoying baseball's second-highest strand rate, but even if he's only average pitcher he'll still have plenty of value if healthy. That's a pretty big risk at this stage in his career, but it's absolutely a risk worth taking.