Dempster entertains on first night of Cubs Convention

Dempster entertains on first night of Cubs Convention

CHICAGO -- Ryan Dempster cracked one-liners, took friendly jabs at former teammates and had the crowd roaring in laughter Friday night on Day 1 of the 30th annual Cubs Convention at the Sheraton Hotel and Towers.

The former Cubs pitcher and current special adviser hosted "Friday Night with Ryan Dempster," a talk show featuring guests such as president of baseball operations Theo Epstein and general manager Jed Hoyer, current players Anthony Rizzo and Jon Lester, and former Cubs Mark DeRosa and Rick Sutcliffe, among others.

The 2 1/2-hour show was a mix of the "Late Show With David Letterman" and "The Tonight Show Starring Jimmy Fallon," blending Letterman's famous Top 10 list and Fallon's skits.

Dempster's Top 10 was "The Top 10 reasons the Cubs hired Joe Maddon:"

10. "We misheard and thought he knew [actress] Eva Longoria."

9. "We're trying to set the Guinness Book of World Records for most fired managers."

8. "We needed someone who would take the leftover Harry Caray glasses."

7. "The Cubs' bus keeps breaking down so we figured, 'Hey, we can use his RV.'"

6. "Most managers take shots from the media; Joe Maddon buys shots for the media."

5. "We have a young team here in Chicago, and if 60 is the new 40, well, we need someone to manage all of our toddlers."

4. "[Model wife of former Cub David DeJesus] Kim DeJesus told us to."

3. "He's the son of a plumber and, let's just face it: the Wrigley bathrooms need a ton of work."

2. "We just feel bad for anyone who lives in Florida."

1. "Well, because of all the other managers we tried to tamper with, none of them called us back."

A few other highlights from the night:

• On Epstein's free-agent pursuit of Lester, an avid hunter: "Theo was willing soak himself in deer urine to go sign Lester. I told him, 'Theo, we can hire someone for that. Let's bring back Moises Alou.'"

• DeRosa said the biggest key to being a good teammate is talking to them. There was one exception, though: "The only guy I never said a word to was Carlos Zambrano."

Dempster, Rizzo play wiffle ball

• Dempster asked Rizzo to name the best/worst of his teammates. Best dressed: Jason Hammel; Worst dressed: Travis Wood. Best singer: former Cub John Baker; Worst singer: Starlin Castro. Best tipper: Edwin Jackson; Worst tipper: former Cub Carlos Villanueva. Best-smelling teammate: Pedro Strop; Worst-smelling teammate: former Cub Emilio Bonifacio.

• The video skits, which were shown between breaks, showed some of Dempster's duties as special adviser. They include fetching Epstein coffee, picking up his dry cleaning and ironing his shirts.

• In one skit, Dempster claimed he dressed up as the Cubs' mascot, Clark, this season. He also said he helped design Clark, and was shown walking through the office with no pants.

Cash Kruth is a reporter for MLB.com. Follow him on Twitter at @cashkruth. This story was not subject to the approval of Major League Baseball or its clubs.