Acknowledging Ryan Dempster’s underappreciated Cubs career

If you’re relatively young in your Cubs fandom, maybe you know Ryan Dempster best for his hosting duties on his Marquee Network show Off the Mound with Ryan Dempster. But for most of us, he’s the quirky hurler who spent nearly a decade on the North Side doing a little bit of everything for the pitching staff.

Hot on the heels of a heartbreaking loss in the 2003 NLCS, Jim Hendry went out and signed Dempster, who was coming off Tommy John surgery as a 26-year-old. He made his Cubs debut late in the 2004 season – and after spending his entire career to that point as a starter, he transitioned to the bullpen.

He opened the next year as a starter, before taking over closing duties – and he took off from there, going 33-for-35 in save opportunities and earning himself a multi-year extension in the process. He spent all of 2006 and 2007 in the bullpen, as well, with varying levels of success. In ’06, he tied for the league lead, finishing 64 games for manager Lou Piniella. However, he blew nine saves that year, as well.

In the spring of 2008, Dempster wound up returning to the starting rotation – to tremendous success, I might add. The veteran right-hander played a critical role for the eventual NL Central champion Cubs, racking up 206 2/3 innings, winning 17 games and earning the only All-Star nod of his 16-year career.

Although he was never quite able to replicate that success, you can’t say enough about the work Dempster did in the rotation from 2008 to 2011. In each of those seasons, he eclipsed the 200-inning mark, making 132 starts and working to a 3.80 ERA and 3.81 FIP for the Cubs.

The end of the line for Ryan Dempster and the Chicago Cubs – as a player

In 2012, Theo Epstein sent Dempster to the Texas Rangers in a trade that wound up paying major dividends down the road for the franchise. It was the deal that netted Kyle Hendricks who, of course, went on to start some of the biggest games in team history, including the clinching contest of the 2016 NLCS and Game 7 of the World Series in Cleveland.

Dempster struggled with the Rangers, but he was still able to land a two-year deal that winter from the Red Sox. At age 36, he finally earned his first and only World Series ring as a player, making three relief appearances for Boston after spending the year in the rotation, going 8-9 with a 4.57 ERA.

Despite having a year left on his deal, Dempster decided to spend the 2014 season with his family, forfeiting more than $13 million in salary. That fall, he officially hung up his spikes for good, closing the book on his big league career.

A true hybrid pitcher, Dempster ranks 24th all-time in WAR for Cubs pitchers, 38th in wins and fifth in saves. He’s not someone who’s ever going to find himself in the new team Hall of Fame inside Wrigley Field, but for most of a decade, he was a steadying presence at Wrigley, doing whatever was asked of him with poise and professionalism – and he’s worthy of remembering.