Ryan Dempster

Ryan Dempster had a long, winding road in professional baseball before arriving in Chicago prior to the start of the 2004 season.

Initially drafted by the Texas Rangers in the third round of the 1995 MLB Draft, Dempster was traded to the then-Florida Marlins in 1996 before making his big league debut. That would come a couple of years later, though he was shelled by the Cubs in first career start for five runs in 1 1/3 innings on June 1, 1998. After making the 2000 MLB All-Star Game, Dempster was traded to the Cincinnati Reds in 2002, though he pitched to a ghastly 6.39 ERA in 204 1/3 innings prior to needed Tommy John surgery in August 2003.

Unwilling to wait out his recovery in the hopes of aiding the big righty in recapturing his former glory, the Reds released Dempster in the 2003-04 offseason. The Cubs swooped in quickly and brought the 27-year-old pitcher in, understanding that he wouldn't be ready until deep into the following season. Once he was ready to pitch again, the Cubs asked him to do something he had only done five times in his career up to that point: enter games out of the bullpen.

That experiment worked wonders, as Dempster recorded 87 saves and a 4.10 ERA out of the 'pen from 2004-07. He took over as the team's full-time closer in 2005 as veteran LaTroy Hawkins faltered in the role. He is the only Cub and one of just three players ever to both start a game and collect 30 saves in the same season. 

In 2008, Dempster was moved into the starting rotation as Kerry Wood was moved to the closer gig in an attempt to prolong his career, and both players responded with an All-Star campaign. Dempster ultimately pitched to a 2.96 ERA (3.41 FIP) and 187 strikeouts in 206 2/3 innings, finishing sixth in NL Cy Young voting that season. From 2008-11, Dempster effectively had a second career with the Cubs as a starter, throwing at least 200.0 innings in every season while racking up a 3.81 ERA (3.80 FIP) and 13.8 bWAR.

One of my favorite things about Dempster was his bizarre glove-wiggle during his wind-up. It was a move he claimed was done in order to prevent tipping opposing batters to his pitches, though I thought it was simply designed to throw hitters' timing off. Either way, it was a big reason in why his starts were always appointment viewing for me as a kid, especially during that absurd 2008 season.

Dempster was involved in a ridiculous trade deadline saga in 2012 that involved a deal to the Braves that he effectively blocked as he sought out a future in Los Angeles with the Dodgers. In the end, Dempster was dealt to the Texas Rangers, the team that originally drafted him, later that July. In return, the Cubs received fringe top-100 prospect Christian Villanueva and a little-known minor-league pitcher by the name of Kyle Hendricks.

Dempster struggled with the Rangers before departing for the Boston Red Sox in free agency. Similar to his frequent dust-ups with Ryan Braun during his time in the NL Central, Dempster became something of public enemy No. 1 in New York when he purposefully hit Alex Rodriguez after the star third baseman had been caught using steroids. Nevertheless, he finally won a World Series ring with the Red Sox in 2013, which led to him sitting out the 2014 season to spend time with family. The 16-year veteran ultimately retired on October 8, 2014.

He was also the Chicago Cubs’ nominee for the Roberto Clemente Award for community service in 2006 and 2008. Dempster remains actively involved with the franchise, having served as a special assistant to Theo Epstein after his retirement, and the former pitcher now works as an on-air talent on Marquee Sports Network.