In the last week or so, multiple media reports have said trade talks for Jackson have escalated to a fever pitch and on Monday Philly.com broke the news that the Eagles decided to move on from the three-time Pro Bowl selection well over a month ago.
On the surface, that all seems strange. After all, Jackson is coming off his best season, compiling 82 receptions for 1,332 yards and nine touchdowns in his first campaign under the offensive genius of Chip Kelly.
On paper, Jackson seems like a perfect fit for Kelly's innovative offensive mind, a versatile player who can line up all over the field and serve as the ultimate home run hitter for ascending young quarterback Nick Foles.
So what went wrong?
The Eagles are still playing up Jackson's potential 2014 salary cap hit, which is well into eight figures, as the biggest issue. The spin there is that the team has cheaper options at receiver like Riley Cooper and Jeremy Maclin, who is returning from a torn ACL, and could draft a suitable replacement like Oregon State speedster Brandin Cooks.
And that's certainly a possibility because Kelly clashed with Jackson early in his tenure in Philly and most are not going to find it all that far-fetched to believe the second-year coach has the hubris to believe a player like Cooks could hit the ground running under his tutelage.
The real elephant is the room here, however, is Jackson's behavior and it's not about his dive-like attitude, his complaints about assistant coaches or his previous belly-aching over money.
Recently, TMZ Sports unearthed a picture of Jackson flashing gang signs with rapper Nipsey Hussle. In the photograph, Jackson was clearly shown throwing a hand signal for the Rollin' 40s Crips, a street gang from the west side of South Los Angeles, Jackson's hometown.
It was the second time in recent months the 2009 All-Pro made that mistake. He also was seen throwing up a Crips gang sign at Washington Redskins defensive back DeAngelo Hall on the field back in September of last season.
Jackson also paid homage to his gang by naming his record label "Jaccpot Records" with the Cs standing for Crips. Meanwhile, in the video of a song titled "Diamonds on My Neck," featuring another famous former crip, Snoop Dogg, DeSean repeatedly threw similar gang signs.
Jackson's apologists correctly say the mere appearance of impropriety means nothing and point to the fact that while his behavior can be described as boorish at times, the star receiver has never gotten into any major off-the- field incidents.
Two league sources, however, confirmed to The Sports Network that an early January burglary in which Jackson was robbed of about $200,000 in cash, $125,000 in jewelry and a handgun raised some serious red flags within the Eagles organization.
It's completely unfair to bring up the name of Aaron Hernandez when discussing the Jackson situation save for one fact -- the Patriots ignored Hernandez's reported gang affiliation for far too long and unknowingly enabled the behavior which eventually put Hernandez in prison, awaiting trial on murder charges.
It's possible and perhaps fair to say Jackson has moved past any real gang ties and only throws signs in an effort to retain some sort "street credibility" for a potential rap career.
His employer, however, is in the process of making a business decision and weighing the pros and cons of keeping Jackson around, a process that reached a tipping points weeks ago.
The Eagles see Jackson as an immature guy more concerned about earning the respect of his "friends" from L.A., a man who sees football as just a job in which his athleticism enabled the money to come far too easily.
In their minds, Jackson's unwillingness or inability to leave a maladjusted group behind despite having the means, opportunity and obligation to do so, was the last straw.