Lester didn't know Dempster all that well yet, which is why he was confused on an early season road trip as to why Dempster had stripped down to his boxers in the back of the bus.
Puzzled, Lester asked what was going on, and Dempster indicated he just needed to watch. Catch the rest of the tale of Dempster's hijinks in the video above, as Lester told the story while sitting down for the Maddon's Post show on 670 The Score on Sunday evening.
You can listen to the entire Maddon's Post show here. It was hosted by Cubs Radio color man Ron Coomer and manager Joe Maddon, and Pearl Jam frontman Eddie Vedder was a guest as well as a variety of entertaining stories were shared.