Ted Lilly
There haven’t been many pitchers to spend extended periods as a Cub in the past three decades, and Ted Lilly only spent three-and-a-half seasons as a North Sider. But Lilly made an impact during that time in a playoff-caliber rotation alongside the likes of Carlos Zambrano and Ryan Dempster.
In that short time, the veteran southpaw amassed a 15.1 WAR, good for seventh among all Cubs pitchers in that stretch and worth nearly three wins more than Jon Lester’s entire stint with the team. He was named an All-Star in 2009 and ended that season with a 12-9 record, a 3.10 ERA and 151 strikeouts in 177 innings. Each year as a Cub ended with a 4.0+ WAR, treating fans to the absolute peak of his lengthy career.
While the Cubs slid into a tailspin in 2010, Lilly was paired at the deadline in a deal with Ryan Theriot to the Dodgers for Blake DeWitt and Brett Wallach.
Starlin Castro
Making his debut during the 2010 season, Starlin Castro was tasked with being the anchor of the transition from the division-winning teams of the aughts to the world champions of 2016. Building that bridge was no easy task and there were some dark times during those years. However, the 20-year-old phenom made an instant impact immediately, finishing fifth in NL Rookie of the Year voting.
In his sophomore year, Castro followed that up with his first All-Star appearance and led the entire National League with a whopping 207 hits. Two more Midsummer Classic selections later, Castro was the catalyst, alongside Anthony Rizzo, as the Cubs continued to improve and pull out of the rebuild.
The young infielder had all the tools to contribute at a high level with the rest of the World Series crop but with the emergence of Addison Russell and Javier Baez and the acquisition of Ben Zobrist, he was ultimately traded to the Yankees for Adam Warren. In turn, Warren was then flipped back to the Bronx with Gleyber Torres in the Aroldis Chapman deal.