Beyond being a "rematch" of Super Bowl XXXIX, a Philadelphia Eagles-New England Patriots Super Bowl brings another juicy storyline: the chance for a Howie Roseman-led organization to defeat Bill Belichick and Josh McDaniels, who once reportedly held Roseman in "low regard."
In 2013, when the Eagles were in the midst of searching for Andy Reid's replacement, one name they considered was then-Penn State head coach Bill O'Brien. O'Brien, who had previously been the offensive coordinator for the Patriots, was probably never a perfect candidate for the Eagles because of a large buyout that the team would have had to pay, though there's no doubt there was mutual interest between the two sides.
With that said, a 2013 report from Penn Live (which is no longer up), suggested that Belichick and McDaniels didn't view Roseman highly:
A potential sticking point for O’Brien regarding the Eagles job could be their new general manager Howie Roseman. The club’s 37-year-old salary cap guru is known to be held in low regard by O’Brien’s mentor, Patriots coach Bill Belichick, and by another strong O’Brien contact, former Broncos head coach and Patriots assistant Josh McDaniels.
Of course, the Patriots weren't alone in this view at the time.
Jason LaCanfora of CBS added this on Roseman during the team's 2013 coaching search:
Rather, very different chatter has been growing in NFL circles for weeks. What’s up with the Eagles job? Why don’t guys want it? What are their concerns?
I wish I had a dollar for every time someone told me one esteemed coach or another advised one of the Eagles’ top candidates not to take the job precisely because of Roseman’s presence there. Roseman isn’t the general manager they should tie their wagon to. It’s clear Chip Kelly wasn’t leaving Oregon for anywhere unless he had a large measure of control over the organization, and owner Jeffrey Lurie has already entrusted that to Roseman. There has been trepidation by some candidates to go all-in given the questions about this existing power structure.
The rumblings about Roseman lacking nuance and foresight, about him turning people off with how drunk with power he’s become, only grow louder as his coaching search grows stranger.
In a January 2015 interview on 97.5 The Fanatic, ESPN's Louis Riddick, who worked in the Eagles front-office with Roseman and has since interviewed for many top front-office positions, was extremely critical of Roseman:
“He has been a constant there through a lot of the change,” Riddick said of Roseman. “It’s no secret. I don’t think him and I will be sharing any Christmas cards anytime soon.”
“I think what’s happened now is it’s the way it should have been for a long time. Let’s put it that way. Now, they’ve finally.. They’ve cleaned it up. Now the people who are doing what they should be doing are doing what they should and the people who shouldn’t have been doing what they were doing .. aren’t.”
“Tom Gamble, you can throw myself in there, they’ve had quality football people there. People who know the game. People with big personalities. Let’s just say they went into Philadelphia one way and left another way.”
What's changed since then?
Carson Wentz would be a nice place to start. After the disastrous year with Chip Kelly at the helm of player personnel, Roseman regained control of player personnel decisions following Kelly's release. He used this power to make a series of moves that will define his career. Roseman traded Byron Maxwell and Kiko Alonso, two pieces acquired by Kelly, along with the 13th pick in the 2016 NFL Draft to the Miami Dolphins for the eighth pick in the NFL Draft. This move not only gave the Eagles a better pick, but it got rid of Maxwell's contract.
As first reported here in April of 2016, the Eagles initially thought they had a draft-day arrangement in place with the Chargers, which would have allowed them to acquire the No. 3 overall pick in that draft. The newly-acquired No. 8 pick would have been part of that package. At the time, this would have allowed them to draft their franchise quarterback, they thought. Instead, the Rams acquired the No. 1 overall pick, nixing this trade. Roseman did attempt to acquire the No. 1 overall pick, but the Eagles simply didn't have the draft ammo, largely due to the Sam Bradford trade, to acquire this pick. Eventually, the Eagles used a five-pick package, which included the No. 8 pick, to acquire the No. 2 pick (and a fourth round pick) from the Cleveland Browns, which they ultimately used to select Wentz, who has blossomed into a star.
On top of Wentz, Roseman built a great support system. He was among Eagles brass that hired Doug Pederson as head coach. Pederson, after a shaky first season at the helm, has been one of the league's five best coaches in 2017. He gave both Pederson and Wentz two other former quarterbacks to work with, offensive coordinator Frank Reich and quarterbacks coach John DeFilippo (who was a college quarterback). He hired Jim Schwartz, former Detroit Lions head coach, as the defensive coordinator. Joe Douglas, the team's vice president of player personnel, has done such a good job working with Roseman that he seems likely to eventually get a general manager gig.
Beyond building a great support system, Roseman seems to have learned from past Eagles transgressions. He made a splashy, although unique, signing of Alshon Jeffery this past offseason, which has paid dividends. He also picked off veterans who have played in winning organizations – Chris Long, LeGarrette Blount and Torrey Smith, none of whom were especially sexy signings, but all of whom have played big roles in the team's playoff run.
The truth is, while Roseman has improved as a talent evaluator in his second stint in charge of player personnel, he was never necessarily a bad executive in terms of making transactions. He's great with the cap, no one ever disputed that. He led the 2013 NFL Draft, which produced Fletcher Cox, Mychal Kendricks and Nick Foles with the first three picks. He fleeced the Buffalo Bills in a 2014 draft-day trade, landing fourth-round pick for Bryce Brown, who was out of the league two years later. He acquired Darren Sproles for a fifth-round pick.
What has really changed in Roseman's second stint in charge of player personnel is that he appears to have built better interpersonal skills. Those skills have allowed him to build a staff and team that are far from being held in low regard.