Dwyane Wade sits down with pioneers in sports, fashion, music, and business for an intimate conversation about their origins, and the reasons they keep pushing to innovate. These are all-time greats talking through memorable moments from their careers, telling intimate, behind-the-scenes anecdotes that we never saw in the press, journeys, struggles, triumphs, and that shared excitement as they push forward to their next challenge.

Episode List

Dwyane Wade on the ’06 Heat Reunion and Why Championships Aren’t Just About Winning

Feb 2nd, 2026 2:21 PM

In this episode of The Check In, Dwyane Wade and Bob bounce between nostalgia, parenting chaos, and life after basketball. Wade reflects on the Heat’s 2006 championship run ahead of its 20-year anniversary, remembering the comeback from 0–2, Pat Riley’s culture, and what it meant to learn how to win at the highest level. Off the court, Wade talks about being in full-time dad “Uber mode,” balancing travel with family, and the funny frustration of raising competitive kids. He shares how golf, photography, and even a quick movie cameo have filled his post-retirement life, plus a powerful reflection on a recent trip to Africa that reconnected him to his roots. The episode also mixes in NBA trade talk, Hall of Fame debates, and a hilarious dive into famous Mandela Effect misquotes, a classic blend of hoops, humor, and real life. Music Credit: Khari Mateen What We Discussed: 00:00 Introduction 01:10 Check-In With Dwade & Bob 12:33 WNBA All-Star Weekend, Extreme Weathers ,& Birthday Celebrations 16:59 Reflections On The 2006 NBA Championship 24:10 Dwyane Wade's Journey In The NBA 29:06 NBA Trade Deadline 33:09 Golf Analog For NBA Players 39:10 Dwade's Early Career & Stan Van Gundy 42:13 Sports: Athletes Expressing Frustration 45:17 The Porsche 49:13 Dwade's Cameo In "GOAT" Movie 54:02 Photography & A Trip To Africa 58:36 Mandela Effect Misquotes 01:03:24 Bill Belichick Is Not A Hall Of Famer?! See omnystudio.com/listener for privacy information.

DWade on Trae Young’s Fresh Start, Ja to Miami Rumors, & Giving Away His Olympic Bronze Medal

Jan 20th, 2026 2:08 PM

In this episode of The Timeout, Dwyane Wade and Bob reflect on growth, perspective, and where they are heading into 2026. Dwyane shares how a recent trip to Japan served as a reset ahead of his birthday, helping him focus less on resolutions and more on finding peace and protecting his mental health. He opens up about a regret from early in his career, admitting he gave away his bronze medal from the 2006 World Games and now sees it as an important part of his story that he wants back. The conversation moves through sports and culture, touching on the shifting landscape of the NFL and NBA, the future of college athletics, and how patience and time are essential for young players to grow. They also lighten things up with talks on fashion, lifestyle choices, and a classic R&B debate that closes the episode on a fun note. Music Credit: Khari Mateen. What We Discussed: 00:00 Introduction 00:54 A Day Ahead In Japan 03:30 Dwyane Gave His Bronze Medal Away! 06:11 A Serene Place Of Many Cultures 09:17 New Year's Approach 16:04 Chase Sapphire Reserve 19:27 Dwyane Wade's Travel Essentials 28:04 The Chicago Bears 31:45 An Unexpected Driving Test 36:14 Mike Tomlin: Fired Or Quit? 43:27 Dry January: No Alcohol 45:30 Trae Young Trade 50:12 NBA Teams Dwyane Wants To Win 54:51 The Amateur Concept & Eligibility 01:01:52 Dunking Every Year Till 50 01:04:17 How Dwyane Spends His Birthday 01:06:25 Dwyane's Quarterly Approach For 2026 01:08:37 Jordeci Vs Boys II Men See omnystudio.com/listener for privacy information.

Why 2026 Means More to Dwyane Wade Than People Realize

Jan 9th, 2026 6:31 PM

In this episode of The Timeout, Dwyane Wade and Bob talk about life, hoops, and perspective, starting with Bob reflecting on a recent trip to Japan with his wife, Lisa, and what it was like experiencing a different pace and culture. The conversation shifts to the NBA, with Dwyane sharing how he prepares for broadcasting, why he believes the NBA Cup matters, and his amazement at Victor Wembanyama’s game. He also gives high praise to the current New York Knicks, calling this his favorite version of the team in decades under Jalen Brunson’s leadership. They close the episode on a personal note, with Dwyane sharing a tense moment from his documentary involving Pat Riley and opening up about finally settling into life in Los Angeles after years of resisting the move. Music Credit: Khari Mateen. What We Discussed: 00:00 Introduction 00:48 Last Checkin For The Year 2025 08:04 5 Days In Vegas 13:59 The Alien: Victor Wembanyama 17:17 Most Improved Player Snub 19:56 Zaire Wade's College Inquiry 24:56 Love & Basketball 29:41 Cleveland: Struggling With Expectations 32:25 The New York Knicks 38:54 The 2006 Championship 50:51 The Jordan Comparison 55:15 The Pat Riley Documentary Moment 58:39 Settling In LA See omnystudio.com/listener for privacy information.

CP3’s Future, Shedeur Rising, and Miami Heat Dreams

Dec 16th, 2025 1:54 PM

In this episode of The Checkin, Dwyane Wade and Bob dive into accountability, leadership, and the standards it takes to win — both in the NBA and in everyday life. Wade breaks down his frustration with the Miami Heat after a tough loss, emphasizing defensive effort, culture, and why holding teammates accountable isn’t always comfortable. That leads into a conversation about Chris Paul as a true “accountability locker room guy,” and how organizations sometimes fail legends by not handling transitions the right way. Beyond basketball, Wade talks about launching On the Fly with Dwyane Wade: Life in Motion, sharing why owning his narrative matters and how the series shows his life behind the scenes. He opens up about fatherhood, being more present with Kaavia, and his desire to build a real community for dads. The episode also touches on relationship effort, the importance of the small things, the Chicago Bears finally building a foundation, praise for Shedeur Sanders’ leadership, and a few light moments about Wade’s dog, Trey, plus his work in art and his golf lifestyle brand, Ace. Music Credit: Khari Mateen What We Discussed: 00:00 Introduction 01:29 Voice Training 04:09 The Dwayne Show 08:16 On The Fly: Life In Motion 12:03 A Glimpse Of Dwayne Wade 15:12 All Access Vlog Vs Life In Motion 16:47 Expressing Vulnerability After Major Surgery 20:34 Fatherhood As A Girl Dad 29:07 The Disrespectful & Loving Life Of Trey 37:11 NBA Accountability & Standards: Chris Paul 56:09 Leadership & Team Culture In The NBA 01:02:30 Business > Winning 01:10:50 Ace: Providing Opportunities In Golf 01:14:32 Chicago Bears: Coach Ben Johnson & Shedeur Sanders 01:19:20 NBA Cup, The Holidays & New Year's Eve 1:20:33 50 Gold Balloons & A Leap Of Faith See omnystudio.com/listener for privacy information.

The Check In: Recreating the Bron-Wade Moment, GOAT Debate Heats Up, Steph in Way of Wade’s & CP3 Retirement

Dec 2nd, 2025 3:15 PM

In this episode of The Timeout, Dwyane and Bob talk about the kind of check-ins men don’t always make space for — the simple “you good?” that actually means something. They get into how they’ve both learned to look out for their people in a more real way, not just through jokes or quick texts. They touch on the basketball stuff that’s been on their minds lately — the Jordan and LeBron conversation, Steph lacing up a pair of Way of Wades, CP3 retiring, and how it feels when younger players show love to moments from their era. Dwyane shares a bit about what life’s been like off the court: hiking with his wife even though he hates nature, filming in Rome, and trying to plan her 50th with all the emotions that come with it. He also talks about turning 44 and paying closer attention to his health. They also go back and forth on the league right now — why the All-Star Game feels off, and why the in-season tournament actually adds something. Music Credit: Khari Mateen What We Discussed: 01:07 The Checkin 03:21 Male Relationships 05:21 Dwade & Bob Go Hiking 09:58 Self Vlog In Rome 11:10 The Lebron/Jordan GOAT Debate 20:50 "Are You Finished Or Are You Done?" 22:55 Iconic Recreations: Jalen Snuggs 27:06 Celebrating Birthdays With Family 32:02 The Prince Of Bel Air 32:59 Steph's Sneaker Free Agency 38:57 CP3: The End Of An Era 43:08 Thanksgiving In Rome 47:57 The NBA Emirates Cup 53:46 Physicals In 2026See omnystudio.com/listener for privacy information.

Get this podcast on your phone, Free

Create Your Podcast In Minutes

  • Full-featured podcast site
  • Unlimited storage and bandwidth
  • Comprehensive podcast stats
  • Distribute to Apple Podcasts, Spotify, and more
  • Make money with your podcast
Get Started
It is Free