Many ballplayers deserve the title, "Red Sox killers", through the years, from the infamous (Bucky Dent) to the lesser known (Gates Brown). A free agent pitcher who seems to have dominated them through the years is Ted Lilly. Let's take a look at his recent career and try to get inside the Red Sox front office's collective psyche concerning Lilly.
First, the thirty-year old southpaw is a career .500 pitcher (59-58) with a 4.52 ERA. For the past three seasons, he is 37-34, with ERAs from 4.06 to 5.56 and an average WHIP ratio of 1.42 (not that great). He's been plagued by the gopher ball, surrendering an average of 26 homers/year during three years as well with a strikeout/walk ratio of 424/228.
From the Jamesian Win Shares perspective, he had 16, 4, and 12 from 2004 to 2006.
For three year splits, he has allowed opponents to hit .249 with .755 OPS against and had similar ERA at home and away. He's pitched about the same before and after the All-Star break but had better winning percentage before (not significant).
Against the Sox in three years he is 5-4 with a .227 average against and 3.27 ERA in 14 starts. Against the Yankees he is 2-6 in twelve starts with a .276 average against and 6.21 ERA.
The Yankees are rumored to be hot on the Lilly trail.
What exactly is Lilly? First, he's pitched in the AL, so it's not like he has to learn to pitch against the iron (Beckett?). Second, he's slightly better than .500 the past three years. Third, he doesn't seem to have much of a 'trajectory', he is what he is. Fourth, he has pitched well against Boston and Baltimore, but poorly against Tampa. Perhaps most important, for the Sox, he hasn't pitched well against the Yankees, and whether it's their lineup or the bright lights, that's pretty compelling stuff.
Verdict: pass on Lilly and hope that the Sox can turn it around against him, learning whatever the Bombers and Rays know.