Cut by the NFL, Crowned in Canada: My Road to Two Grey Cups

Nobody drafted me. That's where this story starts.

I came out of Delaware Valley University — a Division III school most football fans have never heard of — holding the program's all-time receiving records and zero guarantees. No combine invite hype. No first-round handshake. Just film, faith, and a Philadelphia chip on my shoulder.

What followed was a decade most people would have quit on: signed and cut, signed and cut, across the NFL — the Eagles, my hometown team, then Jacksonville, the Chargers, Cleveland, Carolina. Every phone call that started with "we're going in a different direction" was another fork in the road. Quit, or keep going.

I kept going. And the road ran north.

The CFL saved my career — and taught me the game all over again

When I crossed into the Canadian Football League, I had to humble myself. Different rules, different field, different country. I wasn't a hometown story up there. I was just another American receiver trying to earn a locker.

Winnipeg is where everything turned. The Blue Bombers didn't just give me a roster spot — they gave me a football home. And in return, I gave that city everything I had. Two Grey Cup championships later, the undrafted kid from Philly who couldn't stick on an NFL roster was a two-time champion in front of 30,000 people who knew his name.

I also wore Toronto and Ottawa jerseys along the way. Every stop taught me something. But those Grey Cups with Winnipeg — that's the proof I carry that the story isn't over when somebody else says it's over.

What getting cut actually teaches you

Here's what nobody tells you about getting released: the first time breaks your heart. The fifth time builds your identity.

Because eventually you have to answer a question that has nothing to do with football: is your worth attached to a roster spot, or is it attached to who you are when the roster spot disappears?

Every cut forced me back to the same three things. My faith — believing there was a plan even when I couldn't read it. My work — because feeling sorry for yourself doesn't run routes. And my people — the family and city that reminded me who I was when the league told me who I wasn't.

That's the foundation of what I now call the Process of Life. The process doesn't skip the painful parts. The painful parts ARE the process.

Why I talk about it now

Today I run ShowtimeSpeaks and host The Keep Going Podcast out of Philadelphia, and I coach player development at West Chester University. When I sit across from guests — athletes, artists, entrepreneurs — or stand in front of a locker room, I'm not speaking from theory. I'm speaking from ten years of hearing "no" and refusing to make it the final answer.

The two championship rings matter. But the message was never really about the rings. It's about the eight years of getting cut that came before them. If I had quit at cut number three — and believe me, I thought about it — there is no championship, no podcast, no stage, no story.

Whatever your version of getting cut is — the layoff, the rejection letter, the business that folded, the door that closed — the same rule applies.

Keep going. The story isn't over.

— Rasheed "Showtime" Bailey