Robert Bailey talks guarding Jerry Rice vs Randy Moss, His Rise as a Sports Agent, Why the NFL was NOT His Career Plan
NFL: Move the Sticks with Daniel Jeremiah & Bucky Brooks
NFL
4.7 • 3.2K Ratings
🗓️ 28 January 2026
⏱️ 72 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:02.6 | Guaranteed Human. |
| 0:04.4 | I think my welcome to the agent business moment was when one of my clients told me he was going to beat my ass. |
| 0:17.8 | Okay. |
| 0:19.4 | One of my clients told me he was going to beat my ass, I'm not going to say any names. |
| 0:24.1 | No names needed. But, you know, I was, a client had a meeting and I called him and it was the, the meeting time had already passed. |
| 0:36.6 | And he was taking his time. |
| 0:38.2 | And I said, hey, man, you got to be more professional. |
| 0:42.6 | You're still at the house. |
| 0:45.0 | And he said, do you know who you're talking to? |
| 0:47.0 | I'll beat your ass. |
| 0:48.6 | I said, wait a second, bro. |
| 0:51.1 | I'm too old to be fighting. |
| 0:52.6 | I'm a grown man, bro. |
| 0:53.9 | I'm not fighting you it's not |
| 0:55.8 | happening i'm 50-something years old you know what's up everybody on pina tillman and this is the NFL players second acts podcast. And with me as |
| 1:14.3 | always as my trusty co-hosts, Roman Harper. I got nothing. Okay good. Yeah. I'm glad I changed |
| 1:22.0 | it up. He swapped out his shirt on me because the other one got a little musty. He stink. |
| 1:27.2 | But he put a new clean shirt on. You stomp me out. I stumped you out. For the first time, I got to admit, and that hardly ever happens. But I'm really excited about our next guest. His highly successful brother right here, man. He's won a lot. I really want to look back in, ask him a lot of questions and dive into his not only his college career is professional career |
| 1:44.3 | and now his post career as well where he's really killing it we're also good to hear a little bit |
| 1:48.2 | more about his charity his foundation work that he's doing here in the city of miami so go ahead peanut |
| 1:52.5 | 11 year vet he won the super bowl two times twice he won two national championships at the university |
... |
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