Best Ryan Dempster Podcasts (2025)

1
Cubs Open 2022 Season-Roy Wood Jr. Joins the boys - Ep. 50 42:13

Play Pause

3+ y ago42:13

42:13

1st inning: How do we get excited about the 2022 Cubs? 2nd inning: Dissatisfied they didn’t sign any big names in the off-season? 3rd inning: What player are you most interested in watching? 4th inning: Is the rotation better now? 5th inning: Will Contreras last the season? 6th inning: Who are they better than in the NL Central? 7th inning: Roy Woo…

1
Kyle Schwarber 18:45

4y ago18:45

18:45

Former Cubs outfielder, and fan favorite, Kyle Schwarber joins Ryan Dempster on Off the Mound presented by Sloan. During the discussion with Dempster, the pair discuss Schwarber’s 2021 season, including time spent with both the Nationals and Red Sox, his off the field charity work recognizing first responders, Chicago memories and look ahead to the…

1
Patrick Wisdom, Frank Schwindel, Brendan Bayliss of Umphrey's McGee and Carlos Zambrano 29:19

4y ago29:19

29:19

For the first time ever on Marquee Sports Network, Off the Mound with Ryan Dempster was recorded live to a rooftop audience overlooking Gallagher Way after the final home game of the 2021 season. Special guests for the live episode include Cubs players Frank Schwindel and Patrick Wisdom, musical guest Brendan Bayliss from Umphrey’s McGee and former…

1
Jason Heyward 24:34

4y ago24:34

24:34

Cubs right fielder Jason Heyward joined Off The Mound with Ryan Dempster to give some updates from spring training, reflect on big career moments as an Atlanta Brave and as a Chicago Cub and provide more insight on the Players Alliance

1
Ian Happ 19:45

4y ago19:45

19:45

Cubs center fielder Ian Happ joined Off The Mound with Ryan Dempster to share and reflect on the 2020 shortened season, how David Ross handled his first year as manager and how he is gearing up for the 2021 season.

1
Kyle Schwarber / Carlos Zambrano 53:47

4y ago53:47

53:47

Cubs slugger Kyle Schwarber and former Cubs pitcher Carlos Zambrano join host Ryan Dempster.

1
Mike Trout / Anthony Rizzo 20:41

4y ago20:41

20:41

3x MVP Mike Trout reflects on his rise to MLB superstardom, talks golf tricks and learning how to change diapers. World Series champion Cubs first baseman Anthony Rizzo catches up with Ryan and hits on spring cleaning, The Sopranos, being the franchise's hit-by-pitch record holder and his charitable work. Off The Mound with Ryan Dempster, presented…

1
Kris Bryant 31:28

4y ago31:28

31:28

Kris Bryant joins host Ryan Dempster on the latest epsiode of Off The Mound.

1
Jake Arrieta 40:53

4y ago40:53

40:53

Former Cub and current Phillies pitcher Jake Arrieta joined Off The Mound with Ryan Dempster to share memories during the Cubs rebuild up to winning the 2016 World Series and much more.

1
Jon Lester / Sean Casey 17:05

4y ago17:05

17:05

Cubs starting pitcher and 3x World Series champion Jon Lester reflects on his 'I love you man' moment with David Ross during Game 5 of the 2016 World Series and the challenge of coming out of the bullpen in Game 7. Also, find out if the 5x all-star would pick Anthony Rizzo or Kris Bryant if he needed someone to babysit his kids. Then 3x all-star "T…

1
Theo Epstein 21:38

4y ago21:38

21:38

Theo Epstein spent nine seasons with the Cubs from 2012-20, responsible for producing the club’s first World Series championship in 108 years in 2016. Prior to leading the Cubs front office, Epstein served as General Manager with the Red Sox, also helping them break a long championship drought in 2004 with the franchise’s first World Series champio…

1
Bob Costas 38:41

4y ago38:41

38:41

Ryan Dempster welcomes 29-time Emmy award winner and 2018 Hall of Fame inductee Bob Costas to the podcast for an extended interview about all things baseball and his best memories calling Cubs games at Wrigley Field.

1
Biggest off-season questions for the Cubs-WSB-TV Sports Anchor Zach Klein of joins the boys! 52:50

4y ago52:50

52:50

1st inning-Work stoppage shutdown Dec 2nd 2nd inning-Contreras future 3rd inning- Wisdom Silver Slugger finalist 4th inning- 3 biggest holes to fill this off-season? 5th inning- McLeod leaves organization 6th inning- Is a game at Wrigley Field too expensive now? 7th inning- Klein Int 8th inning-Dusty still blames Bartman 9th inning-What if the Cubs…

1
What does the Cubs off-season look like? Chicago Party Aunt Chris Witaske joins the boys! 52:48

4y ago52:48

52:48

1st inning-Final thoughts on 2021 season 2nd inning- New GM in town 3rd inning- First move Hawkins needs to make? 4th inning-Which shortstop do you want? 5th inning- How long before they can contend again? 6th inning- Where do Baez, Rizzo and Bryant end up next season? 7th inning- Witaske Int 8th inning-Favorite TV show or movie filmed in Chicago? …

1
What does the Cubs future look like? Mark Carman from NBC Sports Chicago joins the boys. 48:45

4y ago48:45

48:45

What does the off-season look like for the Cubs? How does this team rebuild? Plus Mark Carman from Fansided, WGN Radio and NBC Sports Chicago joins us. @ryandlieber @thechadgordon @thecarm --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
3 Weeks to Go…Cubs Shift to Spoilers while Evaluating those Left Behind 50:11

4y ago50:11

50:11

Chad and Ryan Breakdown those left behind, look at the Big 3 (Bryant, Baez and Rizzo). --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
The Dog Days of the 2021 Season-Orioles Broadcaster Melanie Newman joins the show! 1:03:20

4+ y ago1:03:20

1:03:20

1st Inning-Jake’s Legacy 2nd Inning-Cubs Lovable Losers Again? 3rd Inning-Does Rafael Ortega have Staying Power? 4th Inning-Can Ian Happ Return to Form? 5th Inning-What New Face Stays in 2022? 6th Inning-Why/Why Not Watch 7th Inning -Melanie Newman Int 8th Inning-Field of Dreams Game Reax/Cubs Rumors 9th Inning-Best/Worst Baseball Movies Twitter: @…

1
Baseball Hall of Fame President Josh Rawitch-Full Interview 18:07

4+ y ago18:07

18:07

Baseball Hall of Fame President Josh Rawitch joins the show. Twitter: @thechadgordon @ryandlieber @cubsconfines @baseballhall @joshrawitch --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
The Great Chicago Cubs Fire(Sale) of '21 Aftermath-Baseball Hall of Fame President Josh Rawitch Joins the Show-Joey Christopoulos Guest Hosts W/Chad 53:56

4+ y ago53:56

53:56

1st Inning-One Week Later-Thoughts of the Great Chicago Fire Sale of 2021 2nd Inning-Jed and Rizzo’s Dueling Messages 3rd-Thoughts in Seeing the Big 3 in other Uni’s 4th inning-Rating the Return/Replenishing the Minors 5th-Is there Reason to Support Rest of Year? 6th-What Needs to Happen to Convince You Front Office/Ricketts Has a Plan 7th inning I…

1
The Calm Before the Trade Deadline Storm. ESPN1000's Carmen DeFalco Joins the Boys and a Special Co-Host joins Chad 44:08

4+ y ago44:08

44:08

Inning 1—Trade Deadline is Upon Us... Who’s next? Inning 2—If you could keep just one, would you keep either Javy & Rizzo or Bryant? Inning 3—Bryant Situation Sketchiness?!?! Inning 4—Who is the Actual Leader of this Team? Is there one? Inning 5—Can this Team Make a Run? Inning 6—What if anything excites you about the future? Inning 7—Interview--Ca…

1
Full interview with Gary Sheffield, Jr. of Outkick Sports 17:53

4+ y ago17:53

17:53

Outkick Sports reporter Gary Sheffield, Jr. joins the show. @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @garysheffieldjr www.theconfines.comBy Chad Gordon and Ryan Lieber

1
The Cubs Fire Sale Begins. CBS 2 Chicago News Anchor Ryan Baker Joins the Show 54:28

4+ y ago54:28

54:28

1st inning-Reaction to first half? 2nd inning-Offense report card 3rd inning-Pitching report card 4th inning-Manager report card 5th inning-What’s next? 6th inning-All-Star Game snore? 7th inning-Ryan Baker Int 8th inning-Pirate to KBO 9th inning-Previewing the 2nd half @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @ryanbakermedia www.the…

1
Full interview with ABC 7 Chicago Sports Anchor Dionne Miller 17:06

4+ y ago17:06

17:06

ABC 7 Chicago Sports Anchor Dionne Miller joins the boys to talk about the future of the Chicago Cubs. @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @dmillerabc7 www.theconfines.com --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
Did Cubs Losing Streak End Their Season? Gary Sheffield, Jr. of Outkick Sports joins the boys. 48:31

4+ y ago48:31

48:31

1st inning-11 straight losses 2nd inning-Who’s to blame? 3rd inning- Arietta on IL will he be back? 4th inning-Players on the trading block 5th inning-What teams make sense? 6th inning-Who should the Cubs keep? 7th inning-Gary Sheffield, Jr. Int 8th inning-Former Cubs All-Stars 9th inning-Should fans continue to pay to see this team play? @thechadg…

1
Is the Cubs season already over? ABC 7 Chicago Sports Anchor Dionne Miller joins the boys! 43:05

4+ y ago43:05

43:05

1st inning-The June Swoon 2nd inning-Why should they sell? 3rd inning-Why should they stay the course? 4th inning-Bullpen busted 5th inning-Time to say goodbye to Jake? 6th inning-Cubs All-Star Finalists 7th inning-Dionne Miller Int 8th inning-Best Ex-Cubs factor 9th inning-In honor of Bobby Bonilla day, what’s the worst contract in Cubs history? @…

1
Full interview with Lou Canellis of WFLD Fox 32 16:46

4+ y ago16:46

16:46

Lou Canellis, Sports Director of WFLD Fox 32 joins the boys to talk about the Cubs 2021 season. @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @loucanellis www.theconfines.comBy Chad Gordon and Ryan Lieber

1
Cubs Scuffle Through The Month-Lou Canellis Sports Director of Fox 32 Chicago joins the boys 47:06

4+ y ago47:06

47:06

1st inning-Silent Bats 🦇 2nd inning-Baez benched 3rd inning-Hot Hendricks 4th inning-Playing out the month 5th inning-Zobrist lawsuit 6th inning-Sticky situation 7th inning-Lou Canellis Int 8th inning-NL Central biggest threat 9th inning-Sandberg anniversary game @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @loucanellis www.theconfines.c…

1
Full length interview with Dani Wexelman of MLB Network radio. 21:06

4+ y ago21:06

21:06

Dani Wexelman of MLB Network Radio joins the show. @thechadgordon @cubsconfines @bearsbarroom @ryandlieber @daniwex www.theconfines.com --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
Will the Real Cubs Please Stand Up. Guest Co-Host ESPN CU’s Lon Tay. Plus MLB Radio Dani Wexelman 38:57

4+ y ago38:57

38:57

1st Inning-Up and Down Week-Cards Domination/Mets Trouble 2nd Inning-MLB Sticky Crackdown 3rd Inning-Nature is Healing: Wrigley at 100% capacity 4th Inning-The Jason Heyward Problem 5th Inning-Rizzo/Heyward Anti-Vaxxers 6th Inning-All Star Voting 1st Round is Out --Break 7th Inning Guest Interview-Dani Wexelman is a host on MLB Network Radio on Sir…

1
Full interview with WLS ABC 7 Sports Anchor Mark Schanowski. 19:26

4+ y ago19:26

19:26

Longtime sportscaster Mark Schanowski joins the boys in this full length interview.By Chad Gordon and Ryan Lieber

1
Cubs Back to 100% at Wrigley-Brenda Hilton of Officially Human joins us the Boys 44:27

4+ y ago44:27

44:27

1st inning-West Coast Woes Trip? 2nd inning-Murray back for Opening Day 2.0 3rd inning-Kenney says Cubs are losing money, do you believe him? 4th inning-New City Connect Uniforms 5th inning-Wisdom is wise 6th inning-More on the IL 7th inning-Brenda Hilton Int 8th inning-Pitchers using substances on ball? 9th inning-Who are the Cubs All-Stars? Find …

1
NPR host, CBS Sunday Morning Contributor, and Huge Cubs Fan Scott Simon Full Interview. 27:04

4+ y ago27:04

27:04

Longtime radio host on NPR, contributor on CBS Sunday Morning and Cubs fan Scot Simon joins the boys in this special edition of the Friendly Confines. --- Send in a voice message: https://anchor.fm/theconfines/messageBy Chad Gordon and Ryan Lieber

1
The Red Hot Cubs Continue to Surge-Mark Schanowski from ABC 7 Sports joins the boys. 49:08

4+ y ago49:08

49:08

1st inning: Winning solves everything 2nd inning: Toughest month of the year? 3rd inning: What should Jed do? 4th inning: Is the Cubs farm system better than advertised? 5th inning: Getting Healthy Again 6th inning: Where does Heyward fit in? 7th inning: Brenda Hilton Int 8th inning: Cubs irked about not having full capacity 9th inning: Lou Gehrig …

1
Full length interview with Iowa Cubs broadcaster Alex Cohen. 26:26

4+ y ago26:26

26:26

Iowa Cubs broadcaster Alex Cohen joins the show. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theconfines.com to join our newsletter. @voiceofcohenBy Chad Gordon and Ryan Lieber

1
Cubs Battle Back Into 1st Place-NPR Host and CBS Sunday Morning reporter Scott Simon joins the boys. 57:13

4+ y ago57:13

57:13

1st inning-How does 1st place sound? 2nd inning-Can the Cubs keep this pace? 3rd inning-Javy creates the play of the week 4th inning-Who do you credit the turnaround to? 5th inning-Is Bryant the early MVP favorite? 6th inning-Hoerner is hurting 7th inning-Scott Simon Int 8th inning- Is Brickhouse the greatest Chicago sports announcer? 9th inning-Do…

1
Full Length interview with NBC Sports-Bay Area host Jessica Kleinschmidt 28:45

4+ y ago28:45

28:45

Jessica Kleinschmidt of NBC Sports Bay Area joins the show. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theconfines.com to join our newsletter.By Chad Gordon and Ryan Lieber

1
Are the Cubs a Legit Contender? Iowa Cubs broadcaster Alex Cohen joins the boys. 50:46

4+ y ago50:46

50:46

1st inning-Is this team where you thought they’d be? 2nd inning-Hoyer disappointed in COVID rates for team 3rd inning-Bleacher seats for vaccinated fans 4th inning-Lester and Schwarber return 5th inning-Next video tribute for a Cub? 6th inning-Rossy says no rules with position players pitching 7th inning-Cohen Int 8th inning- Arm of Steele 9th inni…

1
Up and Down Cubs-Michelle Margaux of the SNY Network joins the boys. 50:42

4+ y ago50:42

50:42

1st inning-Can’t win away from Wrigley 2nd inning-Struggles with RISP 3rd inning-Injuries continue to mount 4th inning-Joc with some shock 5th inning-Davies delivering 6th inning-Who’s the face of the Cubs? 7th inning-Margaux Int 8th inning- What do you miss from today’s game? 9th inning-Rossy finds Dr. Love Find and follow us online on Twitter: @r…

1
Full Length Interview with David Kaplan of ESPN Radio 1000 Chicago. 20:55

4+ y ago20:55

20:55

David Kaplan host of Kap & Hood on ESPN Radio 1000 Chicago. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theconfines.com to join our newsletter. --- Send in a voice message: https://anchor.fm/theconfines/mess…

1
The Cubs Surge-Jessica Kleinschmidt of NBC Sports California joins the boys. 48:41

4+ y ago48:41

48:41

1st inning-Doubleheader Sweep of LA 2nd inning-Are you in favor of 7 inning DH? 3rd inning-Bench providing a spark 4th inning-Best person to lead-off? 5th inning-Injury Bug Bites 6th inning-Should Cubs trade Bryant to White Sox in May? 7th inning-Jessica Kleinschmidt Int 8th inning-Strop leaves Cubs as FA 9th inning-In need of a ticket? Find and fo…

1
Full length interview with Pulitzer Prize winner Ira Berkow of The NY Times. 34:28

4+ y ago34:28

34:28

Our full length special edition interview with best selling author and Pulitzer Prize winner Ira Berkow of the New York Times. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theconfines.com to join our newslett…

1
Cubs Continue to Tease-David Kaplan from ESPN 1000 Chicago joins the boys. 50:31

4+ y ago50:31

50:31

1st inning-From the high to the low 2nd inning-Bryant in MVP form 3rd inning-Baez benched 4th inning-Return of Nico 5th inning-Time to replace Davies with Mills? 6th inning-Who would you keep between Javy, Bryant and Rizzo? 7th inning-David Kaplan Int 8th inning-Rizzo moves up Cubs HR list 9th inning-Mongo McMichael ALS-Angel Hernandez Find and fol…

1
Full length interview with Cubs broadcaster Boog Sciambi of the Marquee Sports Network. 20:35

4+ y ago20:35

20:35

Our special edition of the Friendly Confines with Cubs announcer Boog Sciambi of the Marquee Sports Network. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines @boogsciambi Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theconfines.com to join our newsletter. -…

1
Rough Start Turnaround. The boys welcome Pulitzer Prize winning sports reporter Ira Berkow. 46:09

4+ y ago46:09

46:09

1st inning-Is this who the Cubs are? 2nd inning-Hendricks hurting 3rd inning-Contreras keeping afloat 4th inning-Javy turned down $180M 5th inning-How much should Ross be blamed? 6th inning-What would you do? Golden Cubs Fun Fact 7th inning-Ira Berkow Int 8th Which Ex-Cub would you bring back if you could? 9th inning-Are you happy with the way the …

1
Is it Time for Cubs Fans to Panic?-Part 2 W/ Boog Sciambi 43:54

4+ y ago43:54

43:54

1st inning-Should we be concerned? 2nd inning-No O in offense 3rd inning-Kimbrel the Closer 4th inning-Arrieta shows his stuff 5th inning-Who has been the biggest disappointment so far? 6th inning-Team gets first positive test, still not 85% 7th inning-Boog Sciambi Int Part 2 8th inning-Chafin uses Twitter to get a car 9th inning-Fergie gets a stat…

1
Full interview with comedy legend Tom Dreesen a Chicago Original 36:03

4+ y ago36:03

36:03

Celebrity Cubs fan and comedy legend Tom Dreesen joins the Friendly Confines to talk about his career, his new book and his love for the Cubs. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines @tomdreesencomic Join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.the…

1
2021 Season is here-Cubs Announcer Boog Sciambi joins the boys! 41:31

4+ y ago41:31

41:31

1st inning-Baseball is back! 2nd inning-First hand account of Opening Day 3rd inning-Rizzo doesn’t sign deal 4th inning-Mills in the pen, Adzolay the 5th starter 5th-Covid cancels first series 6th inning-All-Star game leaves Georgia 7th inning-Boog Interview part 1 8th inning-Should players jump the vaccine line? 9th inning- Favorite Opening day me…

1
Gearing up for the 2021 season-Part 2 of our interview with legendary comedian Tom Dreesen. 47:45

4+ y ago47:45

47:45

1st inning-Hoerner optioned to AAA 2nd inning-Hendricks, Arrieta and Davies to start year 3rd inning-Permission of capacity increases to 25% 4th inning-Should Players go all out in Spring Training? 5th inning-Cubs meth bust 6th inning-Sandberg joins Marquee Network 7th inning-Tom Dreesen Int Part 2 8th inning-Cubs public Address Announcer position …

1
Jay Mariotti-Full interview 34:32

4+ y ago34:32

34:32

Jay Mariotti talks to the boys about his career in Chicago, If he’s been blackballed from the business, and his thoughts on the Chicago Cubs. Find and follow us online on Twitter: @ryandlieber @thechadgordon, @bearsbarroom @cubsconfines @mariottisports join us on Facebook: Chicago Cubs Friendly Confines Facebook page Check out our website www.theco…

1
Spring Into the Final Roster Spots-Comedy legend Tom Dreesen joins the show! 47:04

4+ y ago47:04

47:04

1st inning: Roster taking shape 2nd inning: Happy with the bench? 3rd inning: All righties in rotation problematic? 4th inning: Contreras legit MVP candidate? 5th inning: If Kimbrel falters who’s the closer? 6th inning: Beth Mowins to call PxP for Cubs 7th inning: Tom Dreesen Int. part 1 8th inning: What athlete/celebrity would you like to see own …