As a kid—yes, the story goes back that far—Roseman would toss a football around in his backyard and wait for his friends to return from practice to play pickup games. He hoped to become an NFL quarterback, maybe even the next Richard Todd or Ken O'Brien.
But he couldn't even play pee wee football. His mom wouldn't sign the permission slip.
That didn't dampen Roseman's feelings. His love for football went beyond passion. By the time he was 7, he was obsessed.
"From the first game I watched, Jets vs. Bills in 1981, I was incredibly hooked," Roseman said in an interview during which he recalled his career from his expansive office overlooking the field at the Philadelphia Eagles' practice facility.
If nothing else, Roseman's life in the NFL offers a lesson in persistence.
He began reading football magazines, watching games, following all the players and taking notes as a kid. Born in Brooklyn and raised in North Jersey, his favorite team was the New York Jets.
"I would read everything and watch all the games I could," he said. "I remember it would be Labor Day, the last weekend for summer, and my mom would want to go to the beach. I'd tell her I wanted to stay home to watch football."
On a plane ride with his mother and sister to visit his grandparents in Florida, a chance encounter left a lasting impression on Roseman. Little Howie, a Mets fans, wore a New York Yankees cap on the flight.
Roseman talked to Jack Elway the rest of the flight, impressing him with his vast knowledge of football. When the plane landed, Elway gave Roseman's mother a business card.
"I was 7 or 8 years old and he said to my mom: 'I never met a kid this age who is so passionate and knows so much about football,'" Roseman said. "I didn't know anyone in football. That to me was someone who believed in me. My whole life, I held onto that one meeting. When I met John Elway for the first time, I told him this story."
Roseman wasn't blessed with the size or skill to play football—he's 5-foot-10 and 175 pounds, though he wrestled at 125 in high school. But his conversation with Jack Elway made him realize he could still pursue a career in the NFL. From that moment on, it was his goal.
"I was 8 or 9 years old and I would tell people that I wanted to be a general manager in the National Football League, and they would laugh at me," he said.
Roseman not only grew up to fulfill his dream, he did it at a young age. Roseman was only 34 when Eagles owner Jeffrey Lurie named him general manager on Jan. 29, 2010. Three years later, he's still the youngest person in the league to hold that title.
With free agency set to begin in the NFL next week, Roseman is in the middle of a critical offseason for the Eagles. The team finished 4-12 and fired coach Andy Reid after 14 mostly successful years in Philadelphia. Roseman played a key role in luring Chip Kelly away from Oregon to replace Reid. He also made other moves to bolster the front office, including hiring Tom Gamble as vice president of player personnel.
Despite tremendous success for much of the past decade, the Eagles are desperately seeking their first NFL title since 1960. Roseman gladly accepts that challenge.
"Everyone here is committed to winning the Super Bowl," Roseman said. "That's powerful when everyone is united for the same goal and it's all about teamwork."
Considering his own rise to power, you have to think Roseman's team has an honest chance. Whenever it has come to football, the guy simply hasn't taken "No" for an answer—regardless how many times he was rejected along the way.
Roseman was in elementary school when he started evaluating players and making draft predictions. Other kids watched cartoons; he was a draft geek.
"I'd have my draft board and I would sit there with a note pad and pretend I was picking," he said. "This is before the Internet. At that time, I would do this as if I was picking for the Jets. That was throughout my childhood and my teenage years."
During his senior year at Marlboro High School in New Jersey, Roseman began sending letters to NFL teams asking for an internship. He was looking for any way to get his foot in the door.
"I got rejected, rejected, rejected," he said.
Roseman moved onto college, choosing the University of Florida because he loved the Gators. He figured he should try coaching and work up to the front office, so he applied for a job with the football program.
"Again, I was rejected, rejected, rejected," he said.
Roseman moved off campus his sophomore year and found a new roommate who shared his passion for football. His dream was to become an NFL head coach. Like Roseman, he didn't play, didn't coach and had no connections.
The roommate was Jedd Fisch. He's now the offensive coordinator for the Jacksonville Jaguars.
"He'd watch me make picks on draft weekend and make fun of me. I would yell at a pick and he would say: 'What do you know?'" Roseman said. "Then we'd watch games together and he would question a call on a play and I'd say: 'What do you know?'"
Roseman continued sending a round of letters to NFL teams twice a year. When he got rejection letters back, he sent "Thank you" notes. Finally, during his senior year at Florida, former Jets GM Mike Tannenbaum called him. At that time, Tannenbaum worked in New York's personnel department.
"He had an untraditional background, too," Roseman said. "When he called, he said: 'I'll give you 10 minutes and the reason is I was in a situation like that and I can help you for advice.'"
Tannenbaum told Roseman no team would hire him as a scout. He advised him to get a law degree and sell himself as a salary cap expert.
So, Roseman went to Fordham Law School and continued his pursuit.
"Same thing. More letters. More rejections," he said. "I would've worked anywhere. I just wanted an opportunity, a summer internship. I would've worked for free."
By now, though, Roseman wasn't just sending letters to teams. He sent his own scouting reports and individual breakdowns of players by position.
"I think about it now and if someone did that to me, I'd wonder 'Who does this guy think he is?'" Roseman joked.
Roseman even thought about trying to break into the XFL during its brief existence but, before he could apply, he got his first break. Tannenbaum had become the director of pro personnel for the Jets and called to interview him for an internship.
"He said: 'Every three resumes, I see a copy of yours. And then after it, I see letters from you thanking me for rejecting you,'" Roseman said.
After a phone interview, Roseman became a finalist for the job. When he interviewed with Tannenbaum in person, he met former Jets coach Bill Parcells for the first time.
"I go to shake his hand and he says: 'Howie, huh? You sure you want to go with that?'" Roseman said. "I said: 'What do you mean, Coach?' He says: 'I know one guy who goes by Howie and not Howard and he's Howie Long and he's 275 pounds. He's a little more intimidating than you right now.' So that's my meeting with Bill Parcells."
Roseman didn't get the job. Instead, it went to a former graduate assistant for one of the coaches. But Tannenbaum told Roseman he'd recommend him if another team had an opening.
Hoping to stay close to New York, Roseman began calling the Eagles. After former team president Joe Banner sent him a letter saying he'd consider him if a position opened, Roseman stepped it up. He kept calling Banner, but got his assistant instead. He begged her to help him get an interview with Banner and told her to have her boss call Tannenbaum.
Roseman didn't know this at the time, but Banner later told him he did call Tannenbaum—partly to find out if he was dealing with a stalker.
In the end, Roseman didn't get a job after his first meeting with Banner. But he was eventually offered a non-paid summer internship in 2000. The Eagles were still in dingy, old Veterans Stadium then. Roseman didn't even have a desk. Banner made room for him at the end of a table next to his assistant, the same woman Roseman pestered with all those phone calls.
"I remember asking her why she fought for me and she said: 'Howie, I'm from Philly. I love passion,'" Roseman said. "And then she said it was women's intuition. She's an unbelievable person."
Roseman spent the next six months waking up at 4:15 a.m. to catch a train from New York to Philadelphia. He got home late at night. Instead of paying off his student loans, he was accumulating more debt paying for those expensive train rides.
"I was pursuing my dream," he said. "I was in the NFL. No matter how tired I was, when I walked up to the Vet and saw where I was going to work every day, I was fired up, I was energetic and I do the same now."
Roseman would spend long hours in the office during the day and join the guys in the personnel department afterward. He was fortunate that Lurie, Banner and Reid allowed him to learn whatever he could about scouting and evaluating players.
"They would open the door to me and let me watch tape and write reports, so I was doing the cap stuff and contract stuff during the day and then at night they would expose me to personnel, which was my passion and what I wanted to do," Roseman said. "So I was getting trained on that. And then when Modrak left and Tom Heckert came in as GM, I was one of the few holdovers from the front office. I wasn't the new guy on the staff anymore."
Roseman's hard work and diligence paid off. In 2003, he was named the Eagles director of football administration.
"I started doing draft reports and going on the road," he said. "It was an unbelievable experience and I'm very fortunate the people here exposed me to it."
More success followed. In 2006, Roseman was named vice president of football administration. Two years later, he was elevated to vice president of player personnel. Then, after Heckert left for Cleveland in 2010, Roseman replaced him as the Eagles' GM. With Banner and Reid around, it was more of an advisory role.
Now, it's Roseman's show.
"One of the most important lessons that I want to teach my kids when I look back at it is when you have a goal and you decide early enough that you want to achieve it, you are so far ahead of the pack because so many people when they are going through college, they're trying to figure out what they're doing," Roseman said. "So when you are in one direction, you have an edge. Not that it's going to happen, but you have an edge and I was very lucky someone gave me a break."
All he has to do now is win a Super Bowl.
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