VIDEO: Ryan Dempster Roasts Jon Lester & John Lackey At Cubs Convention


If you weren’t already aware, the 31st annual Cubs Convention kicked off yesterday at the Sheraton Grand Hotel. I’m sure there will be a lot of great stuff to come out of this weekend, but it’s going to be difficult to top “Friday Night with Ryan Dempster”. For the second year in a row, the former Cubs pitcher and current special advisor held a talk show type event on opening night and it didn’t disappoint. Dempster was long known as a prankster during his playing days and he certainly didn’t have any problem cracking some jokes at the current Chicago Cubs roster. Here’s a few of the highlights.

On Anthony Rizzo being listed at only one position while guys like Kris Bryant and Kyle Schwarber are all over the place: “Could you be any less diverse? You’re the anti-Ben Zobrist.”


On Kris Bryant’s engagement: “I was told you wanted to do it earlier, but you wanted one more year of control.”


This was supposed to be a crack at David Ross by making fun of his offense as Dempster told him that maybe he should just switch to being a left-handed hitter: “Like if you watch [Jon] Lester try to pick off at first base, you’d think he’s right-handed.”

That’s just funny….and obviously correct.

That certainly wasn’t the last joke made at Jon Lester’s expense. Check out this great video from which shows Dempster having some fun with Lester and new Cubs pitcher John Lackey. Great stuff all around.

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Luke Norris
Luke Norris is a freelance writer, editor, and publisher. He writes on a lot of different topics, but focuses mainly on sports, and that includes being a senior writer here at Sports Mockery. You can follow him on Twitter @THElukenorris, check out his website, The Luke Norris Experience, and like his Facebook page at