PHILADELPHIA — The most remarkable aspect of Howie Roseman’s reign as the Eagles’ decision-maker perhaps lies less in his salary cap manipulation, which is the best in the business, and less in his talent evaluation, which blossomed in the last five years.

Rather, the most remarkable aspect of how he does business is his boldness. His utter audacity. He did it again this week, trading free-agent bust Bryce Huff to the San Francisco 49ers and paying some of the pass rusher’s salary so the team could move on. A lesser club might have held on to Huff for another season. Not Howie. He saw the mistake, the bad fit, and he made the painful, humbling move.

Signing Huff last year was risky, but owner Jeffrey Lurie likes Roseman’s gambles. “He’s not risk-averse. He’s aggressive. That’s what I want,” Lurie said six days before Roseman won his second Super Bowl.

If fortune favors the bold, then Roseman has earned his fortune. No guts, no glory? Plenty of both for him. No risk it, no biscuit? Howie’s well-fed.

The shocking moves don’t include mistakes like drafting JJ Arcega-Whiteside over DK Metcalf or drafting Jalen Reagor over Justin Jefferson, or signing his own players to early-decision, cash-heavy contract extensions. Every GM makes draft mistakes, and every GM tries to follow the Eagles’ template of early extensions.

We saw glimpses of Roseman’s aggressiveness as soon as he returned to power after a one-year exile engineered by Chip Kelly in 2015. You wonder if that period of quarantine, in which Roseman was restricted from any duties beyond money management, created a mindset in which he figured he had nothing to lose.

Because he’s been coming in from the top rope ever since.

Carson Wentz, Part I

In April 2016, Roseman traded two first-round picks, and picks in the second, third and fourth rounds to Cleveland to draft Wentz, a little-known, FCS (Division I-AA) quarterback from North Dakota State, with the No. 2 pick. Roseman made this deal seven weeks after signing incumbent starter Sam Bradford to a two-year, $36 million extension and six weeks after signing Chase Daniel to a three-year, $21 million contract as Bradford’s backup.

Sam Bradford

In September 2016, Roseman not only traded Bradford to the Minnesota Vikings for a first-round pick and a conditional fourth-rounder, he paid $11 million of Bradford’s 2016 salary as well, all because Eagles coaches convinced him that Wentz could be the starter as a rookie. One footnote: Wentz had missed most of the preseason with a broken rib.

Nick Foles

Roseman bled money to re-sign Big Play Nick in 2017, a move steeped in backstory. He convinced Foles not to retire (Andy Reid had done the same the year before in Kansas City). He signed Foles to a two-year, $12 million deal. He then cut Daniel, which incurred an $8 million salary-cap hit, which meant that the Eagles’ cap hit for backup QBs that season was almost $10 million, since Foles’ contract was weighted with guarantees in 2018. However, the Eagles also carried a $5.5 million cap hit into 2018 from Bradford’s signing bonus in 2016 — so they spent almost $16 million against the cap for a position they hoped they’d never use.

This was a move that originated in the brain of Lurie, and it meant spending an unprecedented amount on the position of backup quarterback. However, if not for Foles, the Eagles probably don’t win their first Super Bowl that year.

Jalen Hurts

In 2020, after the fiasco of using Josh McCown as the backup for Wentz in 2019 and losing a playoff game because of it, Roseman used a second-round pick on Hurts, who was considered a gadget, project quarterback by everyone except Lurie, who advocated for drafting him. The pick set the Eagles’ world on fire and, thanks to Wentz’s insecurity, precipitated the next bold move.

Carson Wentz, Part II

By the end of the 2020 season, Wentz had soured on Philly, gotten Doug Pederson fired, taken one look at Nick Sirianni, and forced a trade to Indianapolis. He did so for about 30% of what was then his market value — a conditional first-round pick and a third-round pick — and unprecedented absorption of dead money — almost $34 million. The picks wound up working out, but the cap hit was devastating. It’s OK. Roseman ate it. Two years later, he was back in the Super Bowl.

A.J. Brown

In 2022, Roseman made the draft-night trade with the Tennessee Titans for perceived malcontent wide receiver A.J. Brown, then immediately gave Brown a five-year, $100 million extension. At that point, nobody even knew whether or not the Eagles had a franchise quarterback.

Haason Reddick

In 2022, Roseman signed Reddick to a three-year, $45 million deal, which seemed like an overpayment at the time. But Roseman saw a high-character, local guy (Camden and Temple) and got a massive discount. At the time, Reddick was a late-blooming first-round pick who’d had a couple of pretty good seasons, but he exploded for 30 1/2 sacks in two seasons with the Eagles, including playoffs.

Jalen Carter

In 2023, the Eagles used a fourth-round pick to trade up and draft red-flagged Georgia defensive tackle Jalen Carter, who had legal troubles shadowing him, not to mention questions about his projected professionalism. Within two years, Carter has fully filled the void left by Fletcher Cox as a player and a leader, and is on a career arc that is much cheaper, much sooner than Cox, who is a possible Hall of Fame player.

Haason Reddick, Part II

Entering the 2024 season, Reddick wanted Roseman to give him a contract extension for Year 3, but Reddick wanted too much for Roseman’s taste. Sniffing a holdout, Roseman traded Reddick to the New York Jets for a conditional third-round pick. I consider this a mistake. Yes, Reddick had just one sack after holding out for seven games with the Jets, but there’s no logic in assuming that he would not have continued to be massively productive with the Eagles. His replacement certainly was not.

Saquon Barkley

Pivoting from two decades of minimizing the running back position’s importance, especially running backs with injury histories, last spring Roseman signed Barkley to a three-year, $37.75 million contract. Barkley proceeded to have the best season of any player in Eagles history and led them to their second Super Bowl title.

Bryce Huff

Roseman hoped Huff, whose backstory mirrored Reddick’s, would be as good as Reddick, so last spring he signed Huff to a three-year, $51.1 million deal. He was not. He managed 2 1/2 sacks in 12 games and basically didn’t play in the playoffs. It was a colossal bust.

Saquon Barkley, Part II

Roseman recognized Barkley’s value and, in March, extended Barkley for two years and $41.2 million. This accomplished two things: It delighted the fan base and it sent a message to the locker room that excellence and character will be rewarded.

Bryce Huff, Part II

Huff, a pass rusher by pedigree, never developed into a three-down end. The rapid development of second-year edge rusher Nolan Smith and rookie Jalyx Hunt helped Roseman decide last week to trade Huff to the 49ers for a mid-round pick and pay $9 million of his 2025 salary. Painful, but necessary.

No risk it, no biscuit.

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