2016 Cubs Convention: Friday Night with Ryan Dempster

The highlight of the 2015 Cubs Convention is back again in 2016, as former All-Star Ryan Dempster hosts a late night-style talk show with your favorite Cubs executives, players and alumni. Comedy sketches, baseball stories and off-the-wall interview questions highlight this fan favorite. Scheduled to appear are Theo Epstein, Jed Hoyer, Joe Maddon, Anthony Rizzo, Jake Arrieta, Jon Lester, David Ross, Kyle Schwarber and more.

The 2016 Cubs Convention kicked off Friday night in memorable fashion. Shortly after players and coaches were cheered at the Opening Ceremony, former Cubs favorite Ryan Dempster took to the stage to host the wildly popular Friday Night with Ryan Dempster variety show.

The opening monologue was full of praise of the 2015 season, a campaign that included 97 regular-season wins and a defeat of the rival St. Louis Cardinals in the National League Divisional Series. The mere mention of the NL Central foe brought a chorus of boos from the crowd, which also got excited with every mention of the NLDS win and St. Louis’ current hacking scandal.

It also included praise for some of the newcomers on the team. The size of outfielder Jason Heyward’s eight-year, $184 million deal was something that could not be ignored.

“Jason Heyward won Powerball before it even happened,” Dempster joked.

He also had some fun at the expense of new starter John Lackey, who was a teammate of the host’s in Boston. Aside from jokes about potentially being the father of some current Cubs, the 37-year-old Lackey, had, “made incredible adjustments since they lowered the mound.”

The first guests on the show were President of Baseball Operations Theo Epstein and general manager Jed Hoyer. They discussed how difficult it was to lay out and then execute “Plan A” in terms of offseason goals, something the duo felt they accomplished by landing Heyward and fellow veteran Ben Zobrist.

“It doesn’t happen often, but we felt this was a year to be aggressive,” Hoyer said.

Epstein mentioned that 2015 was the most fun he’d had in baseball to date, crediting the loyal fans and their excitement for the team.

“Jed took over the team from 2012-2014, I took over last year,” Epstein said with a laugh.

Cubs manager Joe Maddon also made an appearance, and kicked off his time discussing how exciting it was to do some charitable work in Chicago this week. On Wednesday, the three-time Manager of the Year hosted “Thanksmas” dinner at the Chicago Help Initiative, an effort to feed the homeless.

He said he had a busy offseason and didn’t have an opportunity to travel like he might have expected. He also cited the season lasting longer as something that pleasantly cut into some valuable post-season free time.

Aside from the purchase of the Cousin Eddie 2, a 45-foot Winnebago, Maddon said he’s spent a lot of the offseason trying to come up with a team message. The skipper also said that with expectations as high as they are, it’s important to get there on the first day and make sure everybody is on the same page. He believes that this is not something that will be an issue given the personnel.

“We have a unique situation,” Maddon said. “There’s such a strong bond among these guys, … we have a chance to do something really special based on the personalities and talents in the room.”

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