Two time MLB All-Star, World Series champion and MLB Network personality Ryan Dempster joins Raffaele Papaiani for Episode 11 of the Bleed Oil Blue Podcast.

Ryan talks Blue Jays playoff hopes, Vladimir Guerrero Jr., the teams to watch in October, and his unforgettable World Series experiences with the 2013 Boston Red Sox and the 2016 Chicago Cubs. He also shares the story behind hitting Alex Rodriguez, talks about facing Barry Bonds and Albert Pujols.

Then the conversation heads to the ice. Ryan looks back on his love of hockey, Edmonton’s Oilers dynasty, and the wild story of skating in a Florida Panthers practice before making a start for the Florida Marlins the next day. Stay until the end for Ryan’s hilarious Harry Caray style trip through classic Oilers history.

Chapters

00:00​ Ryan Dempster joins Bleed Oil Blue

00:42​ Can the Blue Jays make the playoffs?

02:10​ Vladimir Guerrero Jr. and Toronto’s offense

03:15​ The teams to watch in October

03:49​ Winning the 2013 World Series with Boston

07:28​ The story behind hitting Alex Rodriguez

09:19​ Being part of the 2016 Cubs World Series

10:52​ Showing off the World Series rings

12:30​ The pressure of ending the Cubs drought

14:14​ Edmonton, the Oilers and hockey fandom

16:30​ Skating with the Florida Panthers before an MLB start

23:24​ The toughest hitters Ryan Dempster faced

24:45​ The growth of Canadian baseball

26:53​ Analytics, feel and the mental side of baseball

30:44​ Ryan Dempster does Harry Caray on the Oilers

32:32​ Closing thoughts and thank you