He never received the attention and praise that guys like Carlos Zambrano or even Ryan Dempster seemed to regularly receive during their Chicago Cubs careers, but left-hander Ted Lilly was a big piece of the pitching puzzle during his four-year run on the North Side.
Inked to a four-year, $40 million contract during Jim Hendry’s infamous 2006-07 offseason spending spree, Lilly immediately slotted into the Cubs’ starting rotation the following season – even starting the club’s home opener that year at Wrigley Field.
Of course, 2007 marked the first of back-to-back NL Central titles for Chicago and Lilly played a key role in getting the team into the postseason. In that first year with the team, he was very nearly the team’s most valuable pitcher, with Zambrano narrowly edging him in bWAR (3.9 to 3.8) when it was all said and done.
The veteran eclipsed 200 regular season innings in 2007 for the first time in his career, making 34 starts for the North Siders and working to a 124 ERA+. He really shined in April and August, posting sub-2.60 ERAs in each of those months, and was equally effective both at Wrigley and on the road. Unfortunately, he got rocked in his lone postseason start – surrendering six runs on 10 hits in just three-plus innings against Arizona in the NLDS.
But he bounced right back in 2008, picking up right where he left off, leading the league with 34 starts and tossing north of 200 innings for the Cubs. Lilly and Dempster both won 17 games apiece for the 97-win club, giving manager Lou Piniella a formidable punch atop the rotation.
In his final full season with the team, Lilly earned the second and final All-Star selection of his 15-year career. He was the only representative from the Cubs in that year’s Midsummer Classic. His first-half numbers were stellar, with the southpaw putting up a 3.18 ERA in 18 first-half outings.
On the year, he was near-unbeatable at the Friendly Confines. He made 13 starts at home and dazzled to the tune of a 1.87 ERA and 0.920 WHIP. Even as things went sideways, Lilly battled back from midseason shoulder inflammation to give his team a chance late in the season. In five September starts, he posted a 2.08 ERA. Despite his efforts, Chicago went just 3-2 in those games.
Come 2010, the writing was on the wall. It was a tumultuous season for the team, to say the least, and come the trade deadline, Lilly was shipped to the Dodgers along with Ryan Theriot – and after the deal, he made it perfectly clear how much he loved playing for the Cubs.
"“This is a tough concept to grab,” Lilly said. “It’s not something I’m overly excited about. I’m going to miss a lot [in Chicago]. When I go over there and put a Dodger uniform on and meet my new teammates and go out and start competing with them, I’m sure I’ll really enjoy it.”"
Once his playing days concluded, Lilly actually came back to the Cubs’ front office as a special assistant in 2014. He was one of those gutsy, gritty types that left it all on the field every time he pitched – and, for that reason, has always been one of my personal favorite pitchers I’ve watched in my 30+ years as a Cubs fan.