2015 Cubs Convention: Friday Night with Ryan Dempster

Former Cubs pitcher and current front office special assistant Ryan Dempster made his comedic debut in front of Cubs fans Friday night. And if his new role with the Cubs doesn’t work out, the fan favorite may have found a second career on stage.

Friday Night with Ryan Dempster wrapped up the first day at the 2015 Cubs Convention. The show resembled a late night talk show, similar to Jimmy Fallon or Jay Leno. His opening monologue got the crowd into the performance and though the show was ultimately very PG, he warned fans early on that there was “no FCC to monitor.”

One of the jokes that got a lot of laughs was when he explained how the Cubs front office was prepping for the idea that Opening Day might be played with minimal fans in the bleachers. He joked that to prepare for the sight, they just turned footage of old White Sox games.

Along with his standup, there were intermission videos describing Dempster’s importance—or lack of importance—in the Cubs front office. One video explained that the former right-hander was a key component in landing his old teammate Jon Lester to come to the Cubs. This notion was quickly shot down by a dismissive Tom Ricketts. In that same video Lester was asked about the host’s role, where his response was simply “Who’s Ryan Desmpster?”

On-stage guests included the likes of baseball president Theo Epstein, general manager Jed Hoyer, first baseman Anthony Rizzo and newcomers Lester and manager Joe Maddon.

Prior to Maddon’s arrival, Dempster gave a top 10 reasons the Cubs signed the former Rays’ skipper, with the top reason being “Of all the other managers we tried to tamper with, nobody else called us back,” in reference to Tampa Bay’s initial inquiries that the Cubs may have acquired Maddon without going through proper channels.

During Rizzo’s time on stage, he noted that Jason Hammel is the best-dressed player in the clubhouse, while worst-dressed honors went to Travis Wood. Rizzo also participated in a Home Run Derby, with a few fans walking away with autographed baseballs.

Lester took the stage donning a Dempster jersey and a beer. The host quickly gave him a box of Popeyes Chicken to “make him feel comfortable,” a reference to the infamous Red Sox’s 2011 chicken and beer debacle. The two also joked that Lester, who hasn’t recorded a hit in his major league career, will have to face opposing pitching on a regular basis since the switch to the National League.

Overall, a good time was had by all. Though it’s often not recommended, Dempster might be able to quit his day job.

Be sure to follow us all weekend, as we’ll be blogging many of the panels including the Ricketts Family Forum, Joe Maddon and His Coaching Staff and the Cubs Business Operations Update.

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