In late March 2014, Howie Roseman met with a crowd of reporters at the Ritz Carlton in Orlando. He said no topic was off limits except for one: DeSean Jackson.

On Monday, Roseman’s trade for Jackson said plenty about how he felt when he was forced to release the former Eagles wide receiver five years ago. The senior executive has spent much of the last three years undoing Chip Kelly’s moves, and while Jackson’s departure predated the former Eagles coach’s one year in charge of personnel, it was the beginning of a front office struggle that ended with Roseman in exile.

While it’s unlikely that Roseman brought the 32-year-old Jackson back entirely to throw one last shovel of dirt on Kelly, it will at least be a feather in his cap. The particulars of the deal, however, make more sense.

The Eagles sent a 2019 sixth-round draft pick to the Buccaneers in exchange for the receiver and a 2020 seventh rounder, NFL sources said. Tampa was likely to cut Jackson if they couldn’t find a trade, but the Eagles had intradivision competition (Redskins) and they wanted to keep him off the open market.

Jacksons’ desire to return to Philadelphia – he’d been lobbying for a return since 2016 – helped expedite the acquisition and a three-year, $27 million contract extension that replaces the remaining one-year at $10 million he had on his existing deal.

But will Jackson, now at his fourth stop in the NFL, justify the expense? And what becomes of the rest of the Eagles’ receiving corps?

The second question is easier to answer. Jackson will line up primarily on the outside opposite Alshon Jeffery. While his addition may seem to signal the end of Nelson Agholor’s tenure in Philadelphia, at least at his current salary cap number of $9.38 million, the slot receiver is expected to remain and likely not with a restructured contract, a source close to the situation said.

It would take an attractive offer to pry Agholor from the Eagles, but he may be willing to advance a trade by agreeing to a restructuring if it meant he’d go to a team where he would have a bigger role.

The Eagles, on paper, are stacked on offense, and they’re not even done. Aside from their top three receivers, they have tight ends Zach Ertz – the NFL’s reigning leader in catches at his position – and Dallas Goedert, a budding talent with more snaps and targets in his future.

A running back with pass-catching ability will also be added to the mix this offseason.

But the Eagles have lacked a true home run threat, someone who can consistently create space underneath, since Jackson left. Agholor was drafted a year later, but despite his above-average speed, he was initially unable to thrive on the outside. Torrey Smith wasn’t a bust in 2017, and it’s hard to argue with a Super Bowl conclusion, but he didn’t match expectations.

Mike Wallace was signed last year to essentially replace Smith, but he broke his fibula in Game 2 and never saw the field again. The trade deadline move for receiver Golden Tate did nothing to address the deep-ball need, especially when Agholor was unable to adjust to more snaps on the outside.

Overall, the Eagles finished the season with 52 receptions of 20 yards or longer, which was tied for 16th in the league, but their receivers caught only 24 of those passes. Jackson alone had 13 plus-20 catches, even though he played in only 12 games. He also led the NFL in yards per reception (18.9) for the fourth time in his 11-year career.

He’s still a burner and has always excelled at tracking long passes. But if he drops a step, he loses the one attribute that makes him special.

The Eagles had inquired about other comparable receivers over the last few weeks, specifically the Dolphins’ Kenny Stills, league sources said. Stills doesn’t have Jackson’s resume. But he can similarly stretch the field and is younger (by five years) and bigger (by three inches and 25 pounds). Miami declined the offer.

Jackson’s size (he’s listed at 5-foot-10, 175 pounds) was one of several reasons Kelly gave, depending upon the audience, for his release. But he mostly didn’t like him, and believed that his offense had more to do with Jackson’s career-best season in 2013 (82 catches for 1,332 yards and nine touchdowns) than the receiver.

In five seasons since, Jackson never came close to matching those numbers. He averaged 47 catches for 829 yards and four touchdowns over that span, and played in an average of 13 games a season.

He was pretty much drama-free in three seasons with the Redskins, but he openly griped about his usage and the Bucs’ offense last season, and reportedly asked to be dealt before the trade deadline.

Jackson’s six seasons with the Eagles provided many great memories. He was an explosive touchdown waiting to happen at seemingly every touch. His game-winning punt return touchdown against the New York Giants in 2010 stands as one of the greatest plays in franchise history.

But he could be a malcontent. He wasn’t fond of practice and was distracted by his contract situation for two seasons. He suggested that he’d earned a raise after the 2013 season, even though he was only two years into his second deal, and Kelly had decided soon after that he wanted him gone.

Roseman has never publicly said that he didn’t want to part with Jackson. But even if he was on board, he would have never handled his exit the way the Eagles eventually did. When it was leaked that the Eagles were prepared to release Jackson, the market dried up.

Reporters peppered Roseman with questions about Jackson’s status at the owners’ meetings, but he pleaded for a repose. He had already won his share of trades, but here he was now unfamiliar with having no leverage. Kelly backed him into a corner and eventually Roseman had to cut bait.

Five years later, Jackson may not be that big a fish, but considering the Eagles’ needs, he could suffice. Roseman reeled him back in, but how much did settling old scores factor into the decision?