What makes Howie Roseman better than ever as Eagles GM? His former right-hand man explains the ‘insatiable desire.’

Howie Roseman’s passionate, obsessive, and meticulous qualities factor into his day job and have positioned him to leave a legacy as one of the most formidable football executives in modern history.

Over the years, there have been various stories about a young Roseman running his own NFL drafts for his favorite team, the New York Jets.

“I don’t remember what our first season was, but early fourth or fifth grade or something, maybe sixth grade, I don’t know,” former Eagles executive Jake Rosenberg told unCovering the Birds. “That lasted quite a while, and I do remember how serious he was about the draft and how serious he was about the Jets at the time.”

Rosenberg doesn’t remember exactly how and when he met Roseman, but they lived very close to each other and were immediate friends in elementary school in Monmouth County, N.J. Long before fantasy leagues were a thing, the two did rotisserie baseball together.

Rosenberg and Roseman stayed close through middle school and high school and then went their separate ways in college and beyond. Rosenberg went to Penn, studied business, and went into consulting in Chicago, while Roseman headed to Florida and then eventually Fordham Law School.

Roseman didn’t want to become a lawyer. He wanted to work in the NFL and took an entry-level position with the Eagles studying the salary cap. Rosenberg said he never really saw what was coming for his friend: a future NFL general manager.

“I remember the day when he got announced as the GM in 2010 thinking just how unbelievably surreal it was,” Rosenberg said.

Another thing Rosenberg didn’t see coming: that within a few years, he would be right there with Roseman, joining the Eagles as his right-hand man in salary-cap management and handling many contract negotiations with agents.

That began a professional partnership that lasted over a decade. It also gave Rosenberg a front-row seat to Roseman’s rise, fall, and redemption.

“All the things that have gone into getting to this point from 2010 until now all help inform him in everything he does in the process and in the way he goes about his job,” Rosenberg said. “And then you take a look around the league and how much turnover there is, and I think that that advantage isn’t shrinking. It’s probably growing over most teams, most organizations.

“I don’t know what the future lies in terms of whether this is the start of some unbelievable, unbelievable run of Super Bowls, but it doesn’t take away from the fact that I am highly confident that he’s better at his job than he’s ever been.”

There may not be anyone who knows Roseman as well as Rosenberg, professionally and personally. Rosenberg, until recently, was not available to be interviewed because of his position with the Eagles.

What makes Roseman so good at his job?

“There’s a few things I think that make him great,” Rosenberg said. “I think he’s insatiable in terms of his desire to constantly improve the roster. You might be sitting there thinking, ‘This is the 10th offensive lineman. This is whatever number in a position group. Why is this so important at this particular juncture?’ And you’re never going to get a good answer for that, but everything is so important at that moment, he really doesn’t sleep on anything.”

Rosenberg said a second key trait of Roseman’s is his ability to keep tabs on an incredible amount of information and data.

The third big quality Roseman uses to his advantage? His decision-making process.

“At a certain point, he will make a decision,” Rosenberg said. “He doesn’t necessarily need to have everyone’s buy-in. He doesn’t need consensus, necessarily. He trusts himself and his gut and his experience, and that the process is thorough. And whereas a lot of people struggle making decisions and knowing that some people are going to be left out or unhappy, he will do what he thinks is right and then just deal with that. And he just trusts himself implicitly. That’s something that really benefits him.”

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There have been complaints from some Eagles staffers past and present that Roseman hasn’t been transparent enough in his actions. Those criticisms may have had more weight in lean years, but it’s hard to argue with his process since 2020, which has led to two Super Bowl appearances and one title.

As popular as Roseman has become in Philly among fans, and for as much as the Eagles seemingly have been in lockstep internally, there isn’t always going to be approval or a consensus when he does make a decision.

Roseman’s most controversial move of this offseason, trading away safety C.J. Gardner-Johnson, has been met with some criticism from outside the NovaCare Complex and even from inside. Team sources recently told The Inquirer that a few staffers weren’t completely on board. That’s only natural, but only Roseman has all the intel.

“There’s no singular decision that’s made in a vacuum,” Rosenberg said. “Everything has downstream impact in some way, short term, long term. And so just to look at each decision onto itself and evaluate it that way, either media, fan, or even people in the building, it’s got limited meaning.

“And they’re not all going to work. You’re not going to bat 1.000. But I think this is a process-oriented game, and if you have the best process and you stick to it, you’re going to succeed far more than other teams. That’s the game.”

In 2018, after the Eagles won Super Bowl LII, they had the 32nd overall and last pick of the first round of the NFL draft, just as they did seven years later on Thursday.

The Eagles also entered the 2018 draft with no picks in the second or third round and only four overall.

What Roseman got in return for the 32nd pick that the Baltimore Ravens used to draft Lamar Jackson wasn’t bad: two longtime contributors in tight end Dallas Goedert and cornerback Avonte Maddox, and a 2019 second-rounder.

The 2018 draft turned out to be one of Roseman’s better ones. The Eagles also got Jordan Mailata and Josh Sweat.

Mailata was a former Australian rugby player who had no football experience but was notable in terms of size and athleticism. Roseman picked him in the seventh round.

The Mailata pick encapsulated many of the reasons Rosenberg gave for why Roseman has been so successful at his job:

“He could sit there and say, ‘Well, this might not work, but the upside is so disproportionate to the value of a seventh-round pick, this is something we can get behind,’” Rosenberg said. “And I think that that’s where he crushes most people doing his job.”

» READ MORE: Howie Roseman still thinks of himself as an outsider. It gives the Eagles a big edge in the NFL draft.

Rosenberg left the Eagles a year ago. He is now consulting college sports programs as they navigate a changing landscape. He told unCovering the Birds that working with Roseman put everyone a little on edge, but not necessarily in a bad way.

“I think it’s an intense place to work, there’s no doubt,” Rosenberg said. “Good intense. And I think it’s an amazing thing to see come together from that perspective because the roster is like this dynamic thing that evolves over time.

“You may look at it, you may see holes. You may see issues or weak points or whatever. But his ability to just exhaust every single resource — and resources are relationships with agents or teams or potentially media or anywhere he can get information or get an advantage or he may find out that a certain player is available — those are all potential advantages and potential ways to fill holes.

“So yeah, it’s intense in that sense because he’s never just going to accept, ‘OK, well, we’re weak here. We’re just going to let a few guys battle out who have never done it before.’ Because he knows that you’re on the wrong side of the risk, right? Because the goal is never just, ‘Let’s not be too bad.’ The goal is always the highest level. Like, we’re trying to win a Super Bowl.”

When it came to the Chip Kelly dynamic, Roseman wasn’t blameless. The two butted heads.

After Kelly gained control of Eagles personnel in 2015, he not only had Roseman’s office moved out of the football side of operations at the NovaCare Complex, he made sure that Rosenberg and a few other loyalists went with him.

It’s important to note that owner Jeffrey Lurie had given Roseman an elevated title and a new contract with more money, which not only kept him in the building but suggested he wasn’t going all-in on Kelly. But if Kelly had kept winning, it would have been harder for Roseman to return to power in Philly or anywhere else.

Still, Rosenberg never got the impression Roseman contemplated doing something else.

“Give it up like not be an NFL GM anymore? No,” Rosenberg said. “I think that there were maybe some times where it was pretty uncertain what the path was here naturally. We wouldn’t have been able to see into the future and known.

“I don’t think any part of 2015 was, ‘What else am I going to do with my life?’ I think it was, ‘Let’s figure out everything. Let’s take advantage of this time and come back from the dead. Whether it’s here or somewhere else, be as prepared as humanly possible. And never look back.’ And so I think that was the mission. I don’t remember ever having a conversation of him wanting to leave the business or something like that.”

Personality-wise, Roseman’s a fighter. And those instincts kicked in during his exile, which effectively ended after Lurie fired Kelly before the 2015 season finale.

Roseman has always dealt with the stigma of being a “non-football guy” because he came up through the business side of football operations.

“I think that he’s wired a certain way, and he’s incredibly competitive, and he takes this job personally, and always wanted to bring Jeffrey a Super Bowl. And all those things, I think that’s intrinsic,” Rosenberg said. “Do I think there’s also an element of it that he’s taken notes and receipts of all the people who were happy to jump in, take shots when things weren’t great and all that? Absolutely. You can look around at some of the most successful, most driven people and find the exact same criticisms about them or statements about them, because they’re not like everybody else.”

Ten years ago, the traditional notion of an NFL GM being primarily a scout was beginning to wane. Smart teams looking for any kind of edge embraced this new way of thinking. Football operations expanded, and Lurie wanted the Eagles at the forefront of this change.

He felt Roseman was the guy who could put it all together, not only because of his nontraditional background, but because of his ability to juggle multiple tasks so that he could make the most informed decision.

“Anything that could come up, I think that’s something that I learned early on as we were preparing for a negotiation is it’s not good enough to ever get on the phone and be asked a question or have a point come up that we hadn’t considered in advance,” Rosenberg said. “And I think he takes that approach with everything, is you’ve got to cover everything even if it’s way above and beyond before you ever take a step down the road.”

In two years, the Eagles would win their first Super Bowl, and Roseman would be named executive of the year.

Roseman arguably has more sway than any other GM in the NFL. It has, on the surface, affected how Lurie has gone about hiring coaches and kept him from casting a net that includes big names who would want great power. To Lurie’s credit, he has found some good ones, with the last two winning him Super Bowls.

The general manager’s influence goes outside the normal bounds for the job. For instance, when current Eagles coach Nick Sirianni stumbled in 2023, largely because his replacements for defensive and offensive coordinator didn’t pan out, Roseman initiated the Vic Fangio and Kellen Moore hires in 2024.

Roseman has even shown signs of a professional evolution. No move represented a greater philosophical pivot than spending for a free-agent running back: Saquon Barkley.

Acquiring Barkley wasn’t as radical as some have suggested. His contract wasn’t exorbitant, compared to players at other positions. But the Eagles viewed Barkley as a once-in-a-generation running back and projected an increase in production behind their offensive line and with Jalen Hurts also a threat on the ground.

Did they envision an MVP-caliber season? Probably not. But the New York Giants, who let him walk, and other running back-needy teams may have only seen the risk, while Roseman calculated the risk based on all the information he gathered and decided it was worth the swing.

“All risk isn’t the same, right? But in order to really be able to take risk, you have to have enough information where you can kind of categorize the risk to some degree,” Rosenberg said. “I think what he does is [he] gets enough information where he can say, ‘This may not work, but if this works, the upside is going to be significantly more than we’re giving up here.’”

Roseman has now built Super Bowl-winning rosters with two coaches and quarterbacks and nearly different rosters.

“Not to take anything away from the Chiefs, but the formula of a top-five head coach and top-five quarterback we’ve seen is incredibly powerful and does erase a lot of things,” Rosenberg said. “Not to say that our head coach and quarterback are [or] aren’t in those categories, but the fact is that it’s completely turned over. There’s been a ton of turnover, and so I think that makes it super impressive from a team-building and organizational standpoint. I think that that certainly increases the difficulty level.”

What we can definitively say about Roseman the last 20-plus years through his rise, relegation, and redemption: He wants to win.

Rosenberg has no doubt.

“Every fan should just rest easy, knowing that however much they care, he cares every bit as much, if not more,” he said of Roseman. “This is everything that matters to him, in terms of winning, in terms of getting to Super Bowls, and nothing he’s doing is intentionally moving away from that goal.”