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

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Recorded28 Jan 2026

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Show notes

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. The NFL Players: Second Acts podcast is a production of the NFL in partnership with iHeart Media.See omnystudio.com/listener for privacy information.

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