Howie Roseman’s Unlikely Journey to Becoming the Best Exec in the NFL

Howie Roseman / Photograph by Mitchell Leff/Getty Images

Howie Roseman sat onstage at Villanova University’s Sports Law Symposium in March, just a few weeks removed from narrowly losing the Super Bowl. The Eagles have been to four championships since the Super Bowl was established in 1966; Roseman was the general manager for two of them, including the franchise’s first and only Lombardi Trophy. When the team plane arrived home from that historic win in 2018, it was Roseman, the architect, who thrust the silver souvenir above his head, to the delight of everyone around him — the owner, head coach, players, and fans who’d gathered to welcome their triumphant heroes home. It was a “We did it” moment, but the look on Howie’s face — teeth clenched, a sniper’s stare — also suggested a hint of “I did it.”

Over the course of about 40 minutes at the symposium, Roseman and the moderator, ’Nova’s sports law center director and ex-Green Bay Packers general manager Andrew Brandt, traced the former’s remarkable career path: from eager intern to salary-cap expert to GM, a public demotion, and then a triumphant return to power. Good luck thinking of a more fitting keynote speaker, from Philadelphia or anywhere else, for this event, titled “Sports Leagues: Challenges to Enter, Maintain and Remain.”

At one point, Brandt made a few references to Roseman’s “success,” which prompted a chuckle from his guest. “I’d take exception with that,” Roseman said. “I think we’ve had tremendous success.” The evidence is overwhelming: playoff appearances in five of the past six years and eight of his 12 years as GM, five division championships, and the cherry on top, two NFL Executive of the Year awards. “This team has been one of the top four or five in the league for a long time now,” says Pro Football Hall of Fame sportswriter and preeminent Birds historian Ray Didinger. The 2022 Eagles roster was arguably the best in franchise history, and as Didinger points out, every free agent Roseman signed in the 2017 season played a key role in their path to a title: “He’s the guy responsible for building the roster, and not only did he build it — he’s rebuilt it and sustained it. With the NFL’s setup, that’s not easy to do.”

So how did Howie (as he’s known by everyone except perhaps his children) achieve and maintain this tremendous success? I picked the football brains of experts and former GMs to understand what it takes to walk in Howie’s shoes and perhaps peek at the recipe for that magic fairy dust he sprinkles across our beloved, once-­befuddling, now best-of-class Birds. (As a testament to Howie’s current power, one media member declined to talk on the record out of concern for Howie’s reaction; another, former Inquirer columnist and ESPN commentator Stephen A. Smith, hung up on me before I finished my request for an interview, which probably says nothing about Howie but is delightfully on-brand for Stephen A.) From those who accepted my calls, I learned Howie’s story is a “both/and” tale, informed by a lot of nurture but also, like so many of the great sports biographies, with a man at its center who is naturally wired differently from most human beings — a rare visionary who knew, early on and accurately, what he was meant to do and let nothing stop him from achieving it.

A little over a decade ago, I sat down with Howie in his spacious office overlooking the team’s practice field for a profile in this magazine, and the question I aimed to answer was: How did a guy with no football experience on any level end up, at 37, becoming the youngest GM in the NFL? Howie told me a story about when he was eight years old and met John Elway’s dad on an airplane flight. He talked the poor guy’s ear off for two hours. The elder Elway was so impressed by the boy’s acumen that he said he should be on TV. Howie’s takeaway, as a child, was that someone finally believed in him. He’d long been telling people he wanted to one day run a football team.

You may already know the broad strokes of Howie’s biography: He watched the NFL draft on TV back when only the hardest diehards tuned in, and kept binders stuffed with player stats and a draft board in his college apartment. After graduating from Fordham law school, he sent letters — many, many letters — to every NFL team until then-Eagles president Joe Banner finally agreed to meet with this young superfan/stalker, then hired him as an intern. Howie replaced Banner in 2012 and grew from salary-cap guru to talent evaluator, until new head coach Chip Kelly arrived and stripped Howie of control of the team in 2015. When Kelly left two seasons later, Howie returned to his old role, then rose to even greater heights. (A more succinct summary of Howie’s journey was provided by Jason Kelce at the Super Bowl parade: “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!”) His is a roller-coaster redemption story unlike anything in football or any other sport.

He had the mind-set, he had the confidence, he had the fearlessness. There’s very few people in the NFL that frankly have the guts to be aggressive, to look for every opportunity no matter how small it is.” — Joe Banner, on Howie Roseman

Banner saw firsthand the dues that Howie was willing to pay for a chance to realize his childhood dream; instead of having a corner office, Howie sat at the corner of Banner’s secretary’s desk. Even then, there was a self-assuredness to him that both impressed and fit into the organization’s philosophy. “First,” says Banner, who’s now the co-founder of football website 33rd Team, where he blogs frequently, “if we got it wrong, it’s okay. Everybody makes mistakes, but you’ve got to admit it quickly and then fix it. And second, we don’t fear failure.” Banner recalls a pre-draft meeting one year when Howie, still learning the ropes of talent evaluation, pushed back on a highly touted prospect who had impressed most of the “football guys” in the room. “He had the mind-set, he had the confidence, he had the fearlessness,” Banner says. “There’s very few people in the NFL that frankly have the guts to be aggressive, to look for every opportunity no matter how small it is.”

Former New York Giants general manager Ernie Accorsi is familiar with both a fearless leadership style and the feeling of being an outsider in the NFL. In a past life, Accorsi covered the Sixers for the Inquirer and worked in public relations for Penn State and the Baltimore Colts before crossing over into a variety of front-office roles. He’s best known for drafting Bernie Kosar with the Cleveland Browns and then, with the Giants, trading Philip Rivers for future Super Bowl champ Eli Manning in the 2004 draft. But even after he’d spent years on the personnel side of the game, he says, “There were football people who still called me a ‘PR guy.’” The only way to change that label? As Al Davis once said, just win, baby.

Accorsi developed a professional relationship with Howie before retiring in 2007, and it grew into a friendship, with phone calls and lunches over the years — Accorsi was a football “rabbi” of sorts, one mutual acquaintance says. Howie has only recently shed the label of “salary-cap guy,” and Accorsi thinks there’s a motivation factor they both share, having never played or coached the game (much like Banner, who ran a chain of clothing stores and a youth nonprofit before joining the Eagles’ front office). “You’re on trial every day in our business,” he says. “It’s always a challenge. But I think there was a little more with us.”

Howie’s outsider perspective might also serve him in a more tangible way, says Ross Tucker, ex-NFL lineman and now an analyst for Eagles preseason shows as well as NFL and college games and host of the Ross Tucker Football Network. Tucker points to Howie’s use of David Blaine-like magic to pull off trades that often end up heavily in the Eagles’ favor. He mentions the 2022 deal with the Saints that turned into this year’s number 10 draft pick for an Eagles team fresh off a Super Bowl appearance; in another example, Howie traded down with the Dolphins in 2021 and still drafted DeVonta Smith. (It takes an MBA in draft-pick management to keep all of Howie’s moves straight.) “It’s to the point now where I do wonder,” Tucker says, “if the other GMs are conscious of it when he calls them — like, ‘Should I do this? He’s won a lot of these trades recently. Am I sure I wanna be the next one?’” Perhaps the law-school grad and draft-binder assembler has an edge over his peers, who are nearly all from more traditional football backgrounds. “Most GMs are guys who played Division III and got into scouting,” Tucker says. “Howie has the legal background, plus all the negotiating he had to do on the ­salary-cap side. I wonder if that helps when he’s going through trades. I would say that’s his greatest strength. He’s the best trader I’ve ever seen.”

When it comes to the draft, ­Howie’s track record — like those of all GMs, ­really — is a mixed bag. Banner says Howie would probably grade at or below the league average for success based on hits (Fletcher Cox, Lane Johnson) and misses (Danny Watkins, Marcus Smith, Nelson Agholor, Jalen Reagor) in the first round, especially. But until Jalen Hurts transformed from backup to Super Bowl starter, Howie’s most significant draft pick was quarterback Carson Wentz, in 2016. It’s tempting to view Wentz as a failure, given that Howie traded five picks to move up and get him. The newly crowned Eagles franchise quarterback was injured en route to the Super Bowl in 2017 and was upstaged by a journeyman backup who’s now immortalized by a statue outside the Linc. Today, Wentz is unemployed.

The quarterback’s saga, however, illustrates more than one key aspect of Howie’s philosophy — an iron-sharpens-iron strategy honed via learning as much from failure as from success. Dating back to the Andy Reid/Banner era, Howie believes you build a football team around quarterbacks (starter and, as Howie calls his backup, “second quarterback”) and both offensive and defensive lines. (Banner and Didinger note how rare it is that the Eagles have been elite in the trenches for years and project to maintain that dominance for at least a couple more.) Like Accorsi going all-in on Eli Manning, Howie believed in Wentz and pushed his chips forward. “You’re giving up resources, but he took the chance,” Accorsi says. “I called him afterward and said, ‘I really respect that move. You believed in him. That’s how you win championships.’”

When the Wentz wagon fell apart due to injuries and what seemed like flaws in both his mechanics and his leadership, Howie did what few GMs would do, especially with a player he’d signed to a four-year, $128 million extension in 2019: Not only was Wentz on the trading block two years after that contract, but the asking price was high. “Most GMs would have been afraid, like, ‘If I don’t take one of these offers, I could get stuck with this guy,’” says Banner. “But Howie had the guts to step back and go, ‘I believe somebody is going to need a quarterback. I can do better.’ That’s being aggressive, but also being willing to wait and having good instincts.”

Missing on such a high-profile and expensive player might lead some GMs to play it a bit safer in the future, especially in a pressure-cooker market like Philadelphia. “What I thought was noteworthy was that Howie remained aggressive,” says Didinger. “Sometimes, guys get burned and they back off. Now, you just sit there and wait for your pick to come up every year, not trading up or down. Howie maintained the same approach — ‘Okay, that one didn’t work out. Maybe the next one will.’” In a telling moment at the Villanova event, Howie said of the whole saga, “I’m probably living in my own world … but I don’t view Carson as not having worked out.” Wentz didn’t play in Super Bowl LII, but without his MVP-­caliber performance in the regular season, the Birds might not have made it to the dance, and they almost certainly wouldn’t have had home-field advantage in the playoffs. Wentz helped them win a championship, and when it was all over, Howie’s haul for ­Wentz led, either directly or indirectly, to the team’s top wideouts (DeVonta Smith, A.J. Brown) and boom-or-bust defensive tackle Jalen Carter in this year’s draft, plus a 2022 sixth-round pick and a second-round selection next year. One recent headline called the deal “incredibly lopsided.”

Howie Roseman and proud Eagles with the Conference Championship trophy in January / Photograph by Andy Lewis/Icon Sportswire/Getty Images

Howie’s unwavering aggression is all the more surprising when you consider Chip Kelly’s public “benching” of him, as Banner puts it, or “kick in the teeth,” as Didinger describes it. That hit might have crippled a less sturdy soul. Howie moved from the football side of the building to the business offices, in literal exile. He’d attend practices during training camp to maintain a presence but kept a respectful distance. Owner Jeffrey Lurie had the foresight to keep Howie in the family and the good fortune that he didn’t quit. “He was out there all the time, watching, and I think fully believing that he would get another chance,” says Didinger. Then, in 2016, with Kelly gone after two seasons of missing the playoffs and questionable personnel decisions, the former Eagles GM rose like a different bird. “He never flinched,” says Accorsi, who at the time called to offer support. “I was concerned for him. But there was never any phony confidence. It was always conviction.” Rather than cause him to lick his wounds or question himself, the experience only seemed to deepen Howie’s belief in himself.

It takes a unique mental fortitude to withstand such a high-profile vote of no-confidence, and it’s easy from the fan perspective to critique the public side of Howie’s job: roster-building, ensuring depth at key positions, and salary-cap management (most recently, the masterful Hurts contract that’s a true win-win, rewarding the young superstar with a $255 million deal without crushing the team’s ability to sign other players in the future). Behind the scenes and away from the spotlight that falls on all things Eagles, however, no piece of the puzzle is overlooked. It’s a lesson Howie seems to have learned early on from coach Andy Reid, when he first transitioned to the GM role. Reid told his young charge that he’d need to hit the road if he wanted to be ­successful — stay at the Motel 6, build relationships with college programs. At first, Howie didn’t get it; he could watch film on these kids and spare himself the travel and lousy meals. But he soon realized how important it was for his scouts to see him sacrificing like they do, missing time with their families in order to find advantages at the margins, or at Mary Hardin-Baylor U.

Those unseen strategies continue to pay dividends. Fresh off the Super Bowl win in 2018 yet concerned about the alarming injury rate up and down his roster, Howie overhauled the entire medical staff. The result: Last season, every starter was on the field in Phoenix for the championship game, a feat that rarely happens. Ross Tucker sees the same attention to detail on the road with the team, where accommodations and meals are always first-rate, and hears from former players who go elsewhere and find the organizational grass is rarely greener. He also says the Eagles excel in balancing old-school talent evaluation with analytics: “They do a better job of blending the numbers/math guys with the scouting/research people than any other team in the NFL.” Only a fearless outsider would consider a Goldman Sachs head of bank-loan trading with no football experience for a front-office role, as Howie did in hiring Adam Berry as director of football operations and strategy in January.

While it’s easy to focus on Howie’s whiffs, it’s much harder to argue with his track record on the whole, by almost any metric. Accorsi notes that Ron Wolf, the Hall of Fame GM of the Packers, would say there are no .406 hitters in football — a reference to Red Sox slugger Ted Williams’s legendary batting average. “You’re not going to be successful 40 percent of the time,” Accorsi says. “You’re going to make an out, and you’ve gotta get up off the ground, and you can’t let it make you shy. He’s got the courage. If something doesn’t work out, he goes right up to the plate. The next time, he’s ready to swing.”

The Sign, or, more accurately, Howie’s reaction to the Sign, was a sign itself that something had changed. Before a game against the Texans in Houston in 2022, Howie was on the field and noticed a group of Eagles fans chanting his name in the first row. The phenomenon of Birds fans turning road games into hostile territory for the home team is another by-product of the Howie era — one that he delights in and perhaps takes private credit for, as he probably should. (As Howie has said on the topic: “The sweetest sound to me is when we’re on the road and there’s less than five minutes left, and you start hearing that Eagles chant, you know? That’s a special, special thing.”)

Howie headed straight to the fan with a Phillies jersey and a sign that read, “Howie You Are Forgiven!” along with a list of draft busts with their names crossed out: Agholor, Reagor, J.J. Arcega-Whiteside. In the past, Howie likely would have ignored the sign or given a sly chuckle; maybe he’d deliver a mild dad-joke retort and move on. Instead, he acknowledged the fan’s taunt and raised the stakes. “I’m fucking forgiven for your first fucking Super Bowl?” he yelled. “Fuck you!” The Birds fans exploded in cheers — and Howie smiled. This is perhaps the final element of the job, one that Howie seems to have both struggled with and, frankly, had little time to address: fan relations. When video of the Texas showdown went viral, it proved that Howie’s confidence in himself and his approach to every aspect of the job had peaked.

Of course, luck plays an essential role in all things sports, including the fate of a general manager. As Didinger points out, the draft-pick swap that resulted in DeVonta Smith only happens because the Denver Broncos didn’t draft a quarterback, as nearly everyone expected them to. But if luck is the meeting of preparation and opportunity, credit Howie for being nimble and moving quickly to make a deal with one rival (Dallas) to stick it to another (New York) and steal a stud wideout. Howie should probably send Denver a few Edible Arrangements for another reason: It was reported he’d offered to trade for Russell Wilson last off-season, a deal that was only nixed because ­Wilson shut it down. Who knows what Howie would have given up for a quarterback who ended up having his worst pro season? Perhaps Jalen Hurts would now be the centerpiece of the Broncos, and you’re not reading this story about Howie’s genius. Choose your own cliché here: Sometimes it’s better to be lucky than good, and the best deals you make are often the ones you don’t make.

Didinger shares a story about the former head football coach of C.B. West, Mike ­Carey, who invited Ray to speak at a program he put together called Dream Big, designed to motivate students to set goals and aim high. Didinger was honored and happy to participate, but he said the person who really should be the keynote was Howie Roseman. It was about a week after the draft this past April, but Didinger sent the GM a pitch via email. Howie said yes. “I really do believe that whole notion of dreaming big, setting a goal for yourself, and then you’re going to go achieve it, no matter how many people tell you you can’t — that’s Howie’s life story,” Didinger says.

He’s still only 48, so it’s a story that’s far from complete, as Howie himself noted at the Villanova sports symposium. Asked how long he wants to keep doing this grueling yet satisfying work — and, more intriguingly, whether he plans to keep doing it here in Philadelphia — Howie answered the former but was more vague about the latter. “I love what I do,” he said. “I love competing. There’s no part of me that wants to do anything else.” Perhaps the most important contract he’ll negotiate for the future of the Eagles will be his own.

Published as “Howie Did It” in the September 2023 issue of Philadelphia magazine.