The knee-jerk reaction to DeSean Jackson’s recent flirtation with Jay-Z is that Jackson (a) must not be properly focused on football, seeing as signing on with a sports agent of 30 seconds and rap star of, like, forever has to be all about bolstering his career as a rapper and executive, right? and (b) is making a bad business decision in general. That’s why it’s a knee-jerk reaction made by sports fans.
No, Jay-Z’s exploits with Def Jam and Rocaway and, even now, Roc Nation, don’t make him qualified to identify football talent. But for a guy who’s basically doing this for kicks, being able to find up-and-coming players everybody else has overlooked isn’t really a prereq for the gig. Nor is that really the primary concern of the player, who’s inclined to think he’s the greatest thing ever, anyway.
Look at this from Jackson's perspective. What does he want in an agent?
Basically, two things. Someone who can (a) negotiate the best contract the market will allow for, and (b) be trustworthy. Something’s telling me Jay-Z would do just fine swinging a deal (especially with all of the advisers he surely has to work out the fine print behind the scenes). And because he’s not actually a sports agent, by appearances, that by default makes Jay-Z more trustworthy than, well, the entire industry – Jackson's former agent Drew Rosenhaus included.
For Jackson, who after this season is guaranteed only $750,000 of the five-year, $47 million deal he signed last March, that all makes Jay-Z a pretty good guy to have around. Even for strictly football reasons.
As for the company Jackson might keep: Jay-Z’s legal run-ins are less than encouraging. But since being drafted in 2008, Jackson’s never been arrested. Spent a lot of dumb money. Maybe spent money that wasn't his, if you believe Rosenhaus. But never been arrested. You can name lots of players that fall in either (or both) category. The only one to which Jackson belongs is unfortunate, but can't keep him off the field.
In one year of this whole rap thing, Jackson’s kept his nose clean. In one more year, he’s financially no longer the Eagles problem. If what essentially amounts to a contract year for Jackson isn’t enough motivation to live up to it – or, if he simply can't live up to it – he’ll no longer be your problem.