Ted Lilly

Brandon Glick · January 10, 2025

Theodore Roosevelt Lilly III, known to baseball fans as Ted Lilly, pitched in parts of 15 MLB seasons, though his best four were spent with the Chicago Cubs.

Lilly was drafted in the 13th round of the 1995 MLB Draft by the Toronto Blue Jays, though he opted to return to Fresno City College for his senior season. That decision didn't pan out as he hoped, as he slipped 10 rounds in the following year's draft before being selected by the Los Angeles Dodgers. Lilly was part of four(!) trades before making his way to Chicago.

This is going to be a lot, so bear with me. After pitching two seasons in the Dodgers' farm system, Lilly was traded to the Montreal Expos (along with Peter Bergeron, Wilton Guerrero and Jonathan Tucker) to the Montreal Expos for Hiram Bocachica, Mark Grudzielanek and Carlos Pérez. He made his MLB debut in 1999 with the Expos, making nine appearances (three starts). Then, in spring training of 2000, he was dealt to the New York Yankees as the player to be named later from a trade in 1999 that sent Hideki Irabu to Montreal. He is (as far as I can tell) the only player to be traded across millennia. After two-and-a-half seasons in the Bronx, he was traded again to Oakland in a three-team deal that sent Jeff Weaver to New York and Jeremy Bonderman to the Detroit Tigers. Finally, following two playoff-bound seasons with the Athletics, Lilly was traded again to the Toronto Blue Jays in exchange for Bobby Kielty.

Finally finding a modicum of stability in Toronto, Lilly produced multiple solid seasons, including earning his first All-Star nod in 2004. After three seasons with Toronto, Lilly rejected a four-year, $40 million deal from the Blue Jays before agreeing to an identical contract with the Cubs on the same day. The Cubs new manager at the time, Lou Piniella, offered his thoughts on Lilly in a way that only he could:

Quote

"We are looking for starting pitching. He is a competitive guy. He likes to pitch. Left-hander, you know, he's got a good breaking ball, but the good thing about him is that he gives you innings. He gives you a chance to win, and we think that he would be a fine addition to our pitching staff."

Lilly more than lived up to Piniella's apt description of him, accruing 15.1 WAR in 113 starts with the Cubs, logging a 47-34 record, 3.70 ERA (4.14 FIP), 598 strikeouts, and 705 2/3 innings from 2007-10 in Chicago. He was the platonic ideal of an innings-eater, pitching 207.0 innings in 2007, 204 2/3 in 2008, 177.0 in 2009 (his second All-Star campaign), and 117.0 through July of 2010. While Lilly was remarkably consistent for the Cubs and had some brilliant performances, including a near-no-hitter on June 13, 2010, against the White Sox, the most interesting part of his Cubs career was his arrival. Chuck Wasserstrom, who was a member of the Cubs baseball operations staff in 2006 under then-general manager Jim Hendry, wrote the history of the Cubs at the Winter Meetings that year and how the Cubs signed Lilly. It's absolutely worth your time if you're interested in the behind-the-scenes action of baseball.

As aforementioned, the Lilly refused an identical contract from the Blue Jays on the same day he signed in Chicago, but he also was garnering interest from the Yankees. Hendry was dealing with heart problems that week, and was advised by numerous doctors to go to the hospital. Once New York chose to focus their efforts on Andy Pettitte at the eleventh hour, Lilly's agent, Larry O'Brien, called Hendry to say they had a deal as Hendry was stretched out on a gurney with an EKG machine hooked up to him. Right after that, they put Hendry in an ambulance and rushed him to a different hospital where he had a procedure done that may have saved his life.

With all the hoopla surrounding his arrival, Lilly's departure was far less adventurous. In the final trade of his career, the southpaw was dealt back to the Dodgers in a five-player deal that landed Ryan Theriot in L.A. and Blake DeWitt in Chicago. Lilly was brilliant in his half-season with the Dodgers and secured a three-year contract in free agency with them in the 2010-11 offseason, though injuries limited his effectiveness afterwards. Los Angeles ultimately DFA'ed Lilly in July 2013, and while he came close to signing a contract with the San Francisco Giants, the deal fell through due to persistent neck and shoulder injuries.

Lilly officially retired professional baseball in November 2013. He later joined the Cubs' front office as a special assistant in March 2014.

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