Bizarre Moves from Seasons Past: The non-signing of Ted Lilly in the 2006-2007 offseason

Ah, the Bizarre Moves from Seasons Past series. I had a lot of fun with this last offseason, but I hadn’t penned one this year, primarily due to the fact that no ideas for new posts had popped into my head. Until now. I previously covered the trading of Mike Lowell, the non-signing of David Ortiz, the non-signing of after the 2003 season, the non-signing of Vladimir Guerrero and the non-signing of Carlos Beltran.

As fate would have it, the last time we published a “Bizarre Moves” post it focused on , and once again the man born Theodore Roosevelt Lilly III takes center stage (after a cameo yesterday).

As noted in that prior BMfSP post, the Yankees had questionably traded Lilly in a three-way deal between the A’s and the Tigers that resulted in New York acquiring the heralded , who spent a tumultuous year-and-a-half in pinstripes before essentially being run out of town and replaced by a nearing-the-end-of-the-line Kevin Brown.

However, despite dishing arguably their best left-handed pitching prospect since and getting garbage in return, the Yankees had an opportunity to bring Lilly back into the fold during the 2006-2007 offseason, as Lilly hit free agency for the first time. Despite three above-average seasons (and one terrible year in 2005), I seem to recall most of the Yankee blogs I was reading at the time being against the idea of a Lilly reunion (although I’m having trouble remembering who expressed these opinions), fearing he’d be overpaid and ineffective. It was also thought that the Yankees would likely end up getting , until the Red Sox shocked the league and outbid every other team by a considerable margin.

In the aftermath of missing out on Matsuzaka, Brian Cashman followed one of the most ill-advised recommendations in team history and signed a Japanese hurler of his own in . Igawa cost $26 million in posting fees and signed a five-year, $20 million that finally ends after this coming season. Nine days after the Yankees won the rights to Igawa, the Cubs signed to a four-year, $40 million contract on December 8, or $6 million less than the Yankees ended up having to spend on Igawa. Read that last sentence to yourself again. Now feel free to puke.

We’re going to do this two ways. First here’s a graphical rundown of Lilly vs. Weaver in the three years leading up to the 2002 trade (Lilly and Weaver both conveniently debuted in 1999); the one-and-half seasons that followed; Lilly vs. Brown through 2005; Lilly vs. his 2006 Yankee equivalent, which in this case would we’ll choose , as he appears to be the least likely of the Yankees’ top four that season to have been on the Yankees had they had Lilly; then Lilly vs. Igawa in 2007; then Lilly vs. Darrel Rasner in 2008, as there’s probably zero chance Rasner would’ve been on that team had they gotten 200-plus innings out of Lilly; then Lilly vs. in 2009; and finally Lilly vs. in 2010, as it seems unlikely the team would’ve been compelled to trade for Home Run Javy had Lilly been on the staff.

This entire exercise of course requires quite a bit of imagination as well as a a blissfully ignorant acceptance of Michael Kay’s beloved fallacy of the predetermined outcome, as obviously the events and personnel on the Yankees would have changed quite a bit if they had indeed wound up holding on to Lilly all these years. But for our purposes, we’re just going to assume everything stayed the same, since it’s impossible to construct every single possible scenario that could have played out involving Yankee teams of the last nine years.

You can to download the spreadsheet used to create these charts if you are so inclined.

Remember, even though it says “NYY ERA,” etc., from 1999 through 2002 Pre-Trade the “NYY” numbers are ‘s. Interestingly, Weaver basically outperformed Lilly in every facet of the game in the three-and-a-half seasons prior to the 2002 trade, which I suppose supports why Brian Cashman acquired Weaver in the first place. Lilly was actually having a pretty solid 2002 for the Yanks (3.40 ERA, though a 4.25 FIP; however Lilly has outpitched his FIP in almost every season of his career due to higher-than-you’d like walk rates and something of a propensity for the long ball. He’s been able to do this due to strand rates mostly in the mid-70% range and not allowing a BABIP above .300 since 2001. While we know BABIP fluctuates fairly wildly from year to year, nine straight seasons of sub-.300 BABIPs may be more indicative of a repeatable skill than luck), although Weaver was having an absurd campaign, flashing a 3.18 ERA/3.17 FIP and 3.3 fWAR — a mighty impressive total given that the season was barely half over at the time of the trade (July 5).

Weaver would get the best of Lilly through the end of 2002 (1.1 fWAR to 0.1), as the latter spent part of the remainder of the season on the disabled list and when he wasn’t injured, simply didn’t pitch very well. However, the tables began to turn the following year, as Lilly would go on to post the strongest season of his career up to that point, while Weaver struggled mightily and was eventually more or less run of of town after posting a 5.99 ERA (though only a 4.26 FIP). Since then it’s more or less been all Lilly compared to who the Yankees wound up using instead, with the exception of 2005, which was Lillly’s worst season since his sophomore campaign and resulted in Kevin Brown actually out-fWARing him. In the eight-and-a-half seasons since the trade, Lilly has accumulated 21.9 fWAR compared to his Yankee counterparts’ 11.0.

It becomes even more glaring when you look at what Lilly did over the duration of the four-year, $40 million deal he signed with the Cubs and that the Yankees were inexplicably so reluctant to dole out. Here are charts of the last four seasons of Yankee pitching staffs, and where Lilly would have ranked had he been on the team:

Lilly would have been the third-best pitcher on the 2007 and 2008 staffs, and believe it or not, the second-best pitcher on the 2009 World Champion staff. Lilly would’ve likely only have been the fourth-best starter among last season’s group, but plugging him in to fill the spot vacated by would’ve essentially kept the well-oiled machine going instead of having to rely on , et. al.

Now one could make the case that perhaps Lilly’s numbers wouldn’t have ended up quite as shiny had he pitched these last four seasons in the AL East instead of the NL Central, but given Lilly’s success in the American League, I don’t think he would’ve performed too dramatically differently. Lilly ended up accumulating 12.5 fWAR during his four-year deal with the Cubs, while the Yankees mustered 0.9 fWAR out of what likely would’ve been Lilly’s spot. Lilly ultimately provided the Cubs with $53.5 million of value — a $13.5 million surplus. What do the Yankees have to show for Igawa? According to Fangraphs, he was so bad in 2007 he actually should’ve paid the Yankees $1.2 million for letting him “pitch,” and the Yankees ultimately completely wasted $46 million that should’ve been allocated much, much differently.

While we’ll never truly know why the Yankees decided to pass on a reunion with Lilly — who reportedly wanted to come back to the Bronx, as his agent gave the Yankees a chance to match the Cubs’ offer — the decision to do so in the 2006-2007 offseason definitely ranks up there with some of the more baffling moves mad by the front office during the past decade.