Robert Bailey talks guarding Jerry Rice vs Randy Moss, His Rise as a Sports Agent, Why the NFL was NOT His Career Plan

Robert Bailey talks guarding Jerry Rice vs Randy Moss, His Rise as a Sports Agent, Why the NFL was NOT His Career Plan

Author: iHeartPodcasts January 28, 2026 Duration: 1:12:02

From Barbados to the NFL, former DB Robert Bailey shares the story of his football journey. He talks about growing up in Miami, earning playing time as a freshman at the University of Miami, and being part of championship teams during the school’s most legendary eras. Robert breaks down unforgettable NFL moments including a pick-six against Jerry Rice, facing Randy Moss and Michael Irvin, and setting the NFL record for the longest punt return on the same day his son was born. He also opens up about his career-ending neck injury, life after football as a sports agent, and the personal loss that led him to create the Kennedy Kids Foundation.

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Two established voices in football media, Daniel Jeremiah from Move the Sticks and Gregg Rosenthal from NFL Daily, have found a new home for their unfiltered conversations. Their 40s and Free Agents podcast, presented by iHeartPodcasts, is less a formal show and more like eavesdropping on a front office war room where the coffee is strong and the opinions are stronger. You’ll hear them dissect team-building strategies with the precision of scouts, but the dialogue is fueled by the kind of bold, often humorous debates that happen after the cameras turn off. Each episode digs into the critical decisions shaping all 32 franchises, from blockbuster trades and free agent gambles to the subtle draft picks that define a team's identity for years to come. It’s a deep, analytical listen that never loses the passion and occasional chaos of the sport itself, offering a unique blend of insider knowledge and genuine fan-level excitement. Tune in for the sharp analysis, stay for the authentic back-and-forth that only two experts with nothing to prove can deliver.
Author: Language: en-us Episodes: 100

40s and Free Agents
Podcast Episodes
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On this episode of 40s and Free Agents, Daniel Jeremiah and Gregg Rosenthal dive into the biggest remaining questions heading into draft week. The guys break down what stands out most in this year’s class, analyze the ov…
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Duration: 27:02
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