PHILADELPHIA — Anyone who has spent any time around Howie Roseman knows that he has a chip the size of a soccer ball on his shoulder. Through two Super Bowl victories and three Super Bowl berths and his rise into the consensus best general manager in the NFL, he has never bothered to set that boulder down. It would be stunning if he ever did.

This is a man who, at U.S. Bank Stadium in Minneapolis, after the Eagles’ victory in Super Bowl LII, refused to answer a question or accept congratulations with anything other than a show of indignation. More than once, he threw his arms in the air in a V, citing the criticisms that those who covered the team had levied against him over the years, making it clear that he had harbored all that resentment and had been motivated by those doubts. (He apologized later.)

But in those moments, Roseman wasn’t just taking advantage of an easy opportunity to say, I told you so. He also was providing an insight into how and why he has become the most respected, and maybe feared, executive in the league. Within the culture of pro football, he was then, and remains, an outsider, and that status gives him and the Eagles an edge in the talent-acquisition game that defines excellence in the NFL.

It frees him to be bolder in his actions and thinking, to chase a potential star with question marks like Jalen Carter. To give up two high draft picks for A.J. Brown. To draft Jalen Hurts in the second round when the Eagles already ostensibly have a franchise quarterback in place, to have everyone assuming that, with 20 picks over the next two NFL drafts, he’ll make a move or two next week. Or three. Or more.

“Maybe that’s an example of being an outsider, of looking at the league when I was studying it before I got into the league, and then coming into the league and understanding that there were opportunities to maybe get aggressive,” Roseman said Tuesday at the NovaCare Complex.

“With that also comes risk, right? All those moves don’t always work out, and it’s probably more conservative to just stand pat and stay where you are, whether it’s with players on your team or during the draft, and kind of see what comes to you.

“When you trade up in a draft, you’ve got to deal with the consequences of who ends up being there with the slot you move out on. Sometimes you say, ‘Man, I could have sat there and got this player.’ And so you have to deal with that, too. For me, I think that being aggressive has always been part of my DNA.”

That’s no exaggeration, or at least not much of one. As an undergrad at Florida, Roseman was a shrewd and sometimes pushy GM in his fantasy football leagues.

“Would offer lopsided deals to many teams to see who would bite,” one of his competitors in one of those leagues, who spoke on the condition of anonymity, said Thursday. “But overall he made smart deals.”

His approach isn’t different now only in that he has a staff of evaluators under him after having put in years of work to learn how to evaluate players himself, to understand what he was seeing, to complement his professional upbringing on the financial side of football. Because his background is more diverse than other executives, many of whom came up through scouting players, his skills as an executive are more diverse, and honed more sharply, than those peers.

Building a roster isn’t about just finding guys who can play. It’s about finding guys who can play at the right price at the right time for the right length of time. Anyone, for instance, can take Saquon Barkley with the second pick in a draft. The New York Giants and former GM Dave Gettleman did, and it was a waste of Barkley’s greatness to have him stuck on a terrible team, to have him beaten up behind a lousy offensive line, for the first six years of his career.

When Barkley became a free agent, just a few people saw him as Roseman did: a 27-year-old running back so good that he was worth a three-year contract for as much as $38 million, the missing piece to make the Eagles a championship team again.

“He comes up from a background that’s not entirely in scouting,” former NFL executive and agent Andrew Brandt told CBS3 in April 2023. “What I think the NFL is slow to the take on is understanding that when you have 4-billion-dollar assets, or 5- or 6- or 7-billion-dollar assets, you can’t really just hire a scout to run the team. You need someone with negotiating skills, financial skills, business skills … not someone who’s spent his whole career bird-dogging players on college campuses. Howie’s done that, but Howie comes from a financial/business negotiating background.

“Fans know. He has — let’s put this honestly — taken advantage of other general managers who don’t have that background. He has taken advantage sometimes of agents who aren’t skilled in negotiating certain nuances of contracts. … He creates a competitive advantage for the Eagles.”

The draft next week gives him his latest chance to prove what a weapon he has become, to show why he’s still happy to use the word outsider to describe himself. A decade ago, before the Super Bowls and the franchise’s recent success, the quickest and most painful way to cut Roseman was to say that he wasn’t a football guy. The connotation was obvious: He hadn’t played the game, so he couldn’t possibly know the game. Take a look around the league. Who knows it better now?

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