The Cubs' success last year was thanks in large part to youngsters such as first baseman Anthony Rizzo, left fielder/catcher Kyle Schwarber and third baseman Kris Bryant, who were together on stage.
Bryant got engaged during the offseason.
"I was told you wanted to do it earlier, but you wanted one more year of control," Dempster teased Bryant of his proposal, while making reference to the 2015 NL Rookie of the Year beginning the 2015 season in the Minors.
Dempster also praised the versatility of Schwarber and Bryant while going over the team's depth chart, before making one astute observation: Rizzo was only listed at first base.
"Could you be any less diverse?" Dempster asked Rizzo. "You're the anti-Ben Zobrist."
Catcher David Ross also joined in jabbing Rizzo, calling him the worst dressed -- "You're Anthony Rizzo. You can't go out like that." -- and worst tipper, saying the young star can conveniently never find his wallet while out with the team.
"It must be in my other car," Dempster quipped while pretending to be Rizzo. "I took the Range Rover. It must be in the Bentley."
On the topic of Ross' offense, Dempster asked him if he ever thought he might be better off hitting left-handed.
"Like if you watch [Jon] Lester try to pick off at first base, you'd think he's right-handed."
Lester was on stage with right-hander John Lackey, who pitched with Lester in Boston and calls him one of his best friends in the game. Lackey said he got tired of hearing from Lester, who admitted he was like "a crazy ex-girlfriend," during the free-agent process.
"It was like I had a little brother," Lackey said. "I said, 'Don't worry, I'll take a little less money to come to Chicago and everything will be on you this year.'"
Other memorable moments from the night:
• A Dempster video in which he shows the crowd the Cubs' old clubhouse, explains he prefers to shower in a bathing suit and is seen walking to the shower wearing a two-piece bikini.
• President of baseball operations Theo Epstein on keeping up with 61-year-old manager Joe Maddon: "I don't know what kind of blue pill he's taking."
• Heyward reading responses Dempster wrote to "mean tweets" the outfielder received after he left the Cardinals for the Cubs.
• An exchange between Bryant and Dempster, in which Bryant jokingly claims he didn't have a poster on the front of Wrigley Field because of "the whole grievance thing."
"Just a small billboard," Dempster said, referencing Bryant's Under Armour ad adjacent to Wrigley Field that was put up while he was still in the Minors.
• Epstein on the real difference in last season: "[General manager Jed Hoyer] put together the team from 2012-14. I took over in 2015."