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From Unpaid Intern Who Never Played Football to The NFL’s Most Powerful GM: The Unlikely Journey of Howie Roseman

He sent 1,100 letters to NFL teams and rejections stacked “as high as the ceiling”. Here’s how he beat the odds to make his dream a reality.

Detailing the incredible underdog story of award-winning NFL general manager Howie Roseman
Credit-AP/Philadelphia Inquirer/Joker Mag

“Was this guy the most persistent guy in the history of America or was he crazy?”

Most kids grow up dreaming of becoming a professional athlete.

Hitting home runs in the World Series or slinging touchdown passes in the Super Bowl.

But when people asked 9-year-old Howie Roseman what he wanted to do, he knew exactly what to say.

“I’m going to be the general manager of a National Football League team,” he declared.

“They used to laugh.”

Sure, people thought he was crazy.

Here was a kid who never played a single down of football talking about building an NFL roster, scouting talent, and negotiating contracts.  What did he know?

But young Howie was dead serious.

Growing up in Marlboro, New Jersey, Roseman negotiated his first major deal as a young boy: convincing his father (who wasn’t a football fan) to buy season tickets for the New York Jets.

Up in the stands, he didn’t dream of becoming the league’s next superstar quarterback or wide receiver.

He wanted to be the guy who drafted them.

Howie was the only person in his family who cared about sports.  Because his parents didn’t understand football, he wasn’t allowed to play – even if he wanted to.

“It didn’t take long for me to see that with the size difference between me and my friends who were playing, that wasn’t really my career route.”

When he wasn’t at a Jets game with his dad, he watched football on TV by himself and started studying how teams were built.

As he got older, his obsession grew.

By the time he was an undergrad at the University of Florida, Howie had binders packed with player stats and built his own draft boards before every NFL Draft.

He was laser-focused on his dream, but he needed a way in.

Per a 2012 Philly Mag article: “[Roseman] didn’t have any legacy connections inside the league — no uncle who played in the ’70s, no coach who knew his parents. Before Roseman was hired as an intern in 2000, he had as much of an inside track into the game as your average sports talk-radio caller.”

So, between his senior year of high school and his third year of law school, Howie Roseman sent an estimated 1,100 letters to NFL teams.  One letter to each team three or four times a year.

“Rejections stacked as high as the ceiling in any room in your house,” he told Bleacher Report in 2014.

“I never wanted to do anything else. I really didn’t have a backup plan.”

Finally, one of his letters caught someone’s attention – Philadelphia Eagles team president, Joe Banner.

Howie Roseman on sending 1,100+ letters to NFL teams: "Rejections stacked as high as the ceiling in any room in your house. [But] I never wanted to do anything else. I really didn't have a backup plan."

“Was this guy the most persistent guy in the history of America or was he crazy?” Banner asked at the time.

“Should we stay away from him, or should one of us interview him?”

Banner took the interview, and just like that Howie Roseman had his foot in the door.

Officially, he was hired as a salary cap/staff counsel for the Eagles in 2000.

In reality, he was an unpaid, entry-level intern who didn’t even have his own desk.

Yes, really.  He sat at the end of an administrative assistant’s desk, trying to soak up as much knowledge as possible.

“I was 25, fresh out of school, and I had all this energy and ideas,” Roseman said.

“So I started shooting off questions, and she finally turns to me and goes, ‘Enough with the f*cking questions.’”

But Howie didn’t care.  His dream had legs.  This was his opportunity.

“He goes all in at everything he does,” said University of Washington head coach Jedd Fisch, Howie’s college roommate.

“I knew that whatever he said he was going to be, he was going to become.”

Roseman was committed to ascending the ranks.

“When you didn’t know him, it was almost too much,” Banner said.

“Somebody who wants it that badly. I don’t care what it takes. I don’t care about the commute. I don’t care what I get paid. I don’t care what job you give me. I don’t care where I have to sit. That will take care of itself in time.”

Howie Roseman had complete conviction and trusted the process.

“I was very fortunate to get in and be exposed to every different area of the business,” he said at Villanova’s 2023 Jeffrey S. Moorad Sports Law Journal Symposium.

“In an industry where people don’t really stay in one place, I was able to kind of move up, and get different jobs, and all through the same organization.”

Three years after landing the unpaid internship, Howie was elevated to director of football administration in 2003.

Three years later, he was promoted to vice president of football administration, where he evaluated players for the NFL Draft and represented the team to the NFL on contract, salary cap, and player personnel matters.

Then on January 29th, 2010, he was named general manager of the Philadelphia Eagles – becoming one of the youngest GMs in NFL history.

The move sparked a firestorm of criticism.

How could a guy with no playing experience be the one calling the shots?

“I bet the rest of the NFC is scared now,” one Delco Times commenter sarcastically declared. “Another bean counter.”

“Don’t you get it?” another asked. “They hire YES men.”

In his first season as GM, Roseman restructured the roster into one of the league’s youngest and won the NFC East.

Still, he faced backlash from all directions.  And it wasn’t just faceless internet commenters.

Scouts gave him the side-eye and his own players questioned his competence.

In 2012, then-Eagles cornerback Asante Samuel took his shot at Howie and the team’s front office: “They’ve probably never played football…It’s a business, and they run it like a business…They’re playing with a lot of money, playing fantasy football, doing their thing.”

But Roseman stayed focused.  His eyes fixed on bringing the coveted Lombardi Trophy to Philadelphia for the first time in franchise history.

“No one wants to see you be successful,” he said. “You gotta…be able to push through the negativity that you’re gonna inevitably face if you want to be successful.”

That’s exactly what he did.

Roseman replaced Joe Banner in 2012 and went from salary-cap savant to bonafide talent evaluator.

Then, the train went off the rails.

New head coach Chip Kelly came in and stripped Howie of team control in 2015.

It was a very public exile.

Roseman was moved to the other side of the building – pushed to the side, just as he was 15 years earlier as the entry-level intern.

It would’ve been easy to give up or jump ship.  But Howie stuck it out.

“He was out there all the time, watching, and I think fully believing that he would get another chance,” said Hall of Fame sportswriter Ray Didinger.

After Kelly got fired a short while later, Howie returned to his old role with a chance for redemption.

A quote from Eagles GM Howie Roseman that says: "No one wants to see you be successful. You gotta be able to push through the negativity that you’re gonna inevitably face if you want to be successful."

We all know what happened next.

Howie Roseman was the architect who helped bring Philadelphia their first Super Bowl championship.

As Jason Kelce said in his famous Super Bowl parade speech: “He was put in the side of the building where I didn’t see him for over a year!… He came out of there with a purpose and drive to make this possible!”

Howie Roseman pulled it off. He went from an underdog with no connections or football experience to a Super Bowl Champion and award-winning NFL GM.

Today, he’s a two-time PFWA Executive of the Year (2017 and 2022) and one of the most powerful executives in professional sports.

“Adversity is okay,” he said. “It humbles you [and] it puts you back on path.”

Paired with unwavering confidence, his complete obsession with football carried Howie down an unlikely path.

To this day, that passion shines through.

Every year, the Eagles’ media kit lists ‘fun facts’ for each player and exec: Favorite movies, books, TV shows, and finally – “If you were not in football, where would you be?”

Howie Roseman’s response?

“Looking for a way to get into football.”

Editor’s Note: This story was requested by a reader of The Underdog Newsletter. Join him and 14,500+ others who get it every Sunday! 👇

Written By

Division III baseball alum (McDaniel College) and founder of Joker Mag. Sharing underdog stories to inspire the next generation.



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