How Deep Is DeSean Jackson Into the Rap Game?

Giant-medallion deep.

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You look at the smoking-hot yellow Ferrari Lamborghini, and the medallions—as large as Olympic medals—around the necks of those who have taken it over, and you wonder. Where is it all going? Who is shelling out the coin? And is it leading the Eagles’ star wide receiver down the wrong path?

For today, the explanation is simple. Jaccpot Records—of which DeSean Jackson is the CEO—is doing a video shoot in Los Angeles. The men standing in and around the world-class machinery represent the growing stable of talent that Jackson is collecting, hoping that they become world-class themselves. The props are part of the shoot, present to send a signal that their music label is on the rise.

“It was pretty good, man. It was actually one of our first serious shoots right now, me and my artists working on a Jaccpot compilation album,” says Jackson. “We just put that first whole weekend of shooting down.”

Jackson says that it’s set to drop, finely enough, right around the start of training camp this July. And this is no project that he is simply watching from the sidelines: Jackson confirmed that he performs on the album. This doesn’t come as any great surprise, as the Los Angeles native, who has long enjoyed a tight relationship with Snoop Dogg and a deep interest in the music industry, can be found all over Youtube rapping with his Jaccpot brethren.

He holds his own.

(Go to the three-minute mark.)

From what I hear, Jackson is being touted as a legit artist within the music circle that he runs in. It is not all about discovering talent and adding to a pool that currently includes the likes of Kid Cali and Gillie Da Kid, but Jaccpot is also a vehicle to explore his own abilities.

And on one hand, so what? One person I spoke with offered this analogy: If Tony Romo can dedicate so much of his off time to playing golf and make bids to qualify for the U.S. Open, why can’t Jackson cultivate his own passions in his spare time? Is it because golf doesn’t scare white America, but rapping does?

There’s at least a strain of truth in there. The pursuit alone is harmless enough.

But there’s another side to it. And like most things, it comes down to money. How is this venture being funded?

Jackson made a few waves this time last year when he bragged about spending $25,000 at an L.A. club during the launch party for Jaccpot Records, a boast Kid Cali helped along by tweeting out a receipt. Just this past weekend, Jaccpot held a party at the Beverly Night Club to celebrate the video shoot.

Even under the assumption that there are sponsorships taking some of the pain out of these bills, there are still plenty of expenses to go around. There’s studio time. Travel. And, yes, Lamborghini rentals. As the CEO, that is Jackson’s load to bear.

It’s a champagne and diamond world he’s funding, and it ain’t cheap.

Some close to Jackson are worried. The level of concern ranges from “This is an unnecessary distraction in the prime of a promising football career,” to “If he stays on this course he could end up in significant financial distress.”

To those who look at the situation pragmatically, it is an unnecessary risk. Why gamble on an industry stymied by 99-cent downloads and filled with temptations of the highest order?

Of course, Jackson was no doubt warned about the unlikelihood of making it as a professional football player as well. He made it out of a tough neighborhood and went from zero to $51 million based largely on ability and willpower.

He’s going back for a second act, with the hopes of bringing some of the old boys along for the ride.

“It’s just a different lifestyle and things like that I’m getting into,” says Jackson, “and just kind of helping out my boys that I grew up with, and just hopefully make it a career as far as rapping and things like that.”