Ryan Dempster on Blue Jays, World Series Rings & Pavel Bure | Episode 11 episode artwork

EPISODE · Aug 27, 2026 · 33 MIN

Ryan Dempster on Blue Jays, World Series Rings & Pavel Bure | Episode 11

from Bleed Oil Blue Podcast · host Raffaele Papaianni

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 Blue00:42​ Can the Blue Jays make the playoffs?02:10​ Vladimir Guerrero Jr. and Toronto’s offense03:15​ The teams to watch in October03:49​ Winning the 2013 World Series with Boston07:28​ The story behind hitting Alex Rodriguez09:19​ Being part of the 2016 Cubs World Series10:52​ Showing off the World Series rings12:30​ The pressure of ending the Cubs drought14:14​ Edmonton, the Oilers and hockey fandom16:30​ Skating with the Florida Panthers before an MLB start23:24​ The toughest hitters Ryan Dempster faced24:45​ The growth of Canadian baseball26:53​ Analytics, feel and the mental side of baseball30:44​ Ryan Dempster does Harry Caray on the Oilers32:32​ Closing thoughts and thank you

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Ryan Dempster on Blue Jays, World Series Rings & Pavel Bure | Episode 11

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