A hypothetical question.

You go to jail for an entire year, at the height of your career for buying a small arsenal of weapons, in the parking lot of a shopping mall, on the night of the BET Awards, at which you happen to be a featured performer. You’re facing fed charges that could land you in prison for over ten years, yet you only have to serve a year, probably because you are famous and, in all likelihood, snitched. You tailor everything you’re involved in career-wise to play nicely with this most inconvenient turn of events; a reality show about turning troubled youth away from crime, an album chockfull of earnest sentiments about regret and “turning over a new leaf,” another reality show featuring your longtime girlfriend and babymomma coming to grips with your incarceration, etc. The album is straight crack, your community service requirements have been met, and therefore all seems to have been salvaged.

When you begin serving your time, numerous shout-outs, aforementioned reality shows, and pre-recorded tracks flood the marketplace, successfully keeping your name and work relevant. You receive a hero’s welcome upon your release, and you immediately begin your reinsertion into the pop cultural landscape. You star in and produce a film that tops the box office the week of its release, put out a few solid tracks in advance of a highly anticipated new album, and land a few impressive guest appearances on high profile records.

But when disaster strikes twice and you’re arrested yet again, this time bringing your aforementioned babymomma and now-wife along with you, you’re left with a most confounding predicament; how do you not make the public think you’re irresponsible, idiotic, ungrateful, and potentially addicted to meth, while also staying out of prison?

Sucks right? Well this is exactly the uphill battle currently burdening rapper, actor, and former/future jailbird, T.I.

T.I. and Tiny were arrested Wednesday night in Los Angeles after cops smelled marijuana coming from their vehicle during a traffic stop off Sunset Blvd. Upon searching the vehicle, officers found what has only been described as a “controlled substance,” and both were ultimately booked on drug possession charges. T.I. is currently under three years of fairly strict probation, so this is not a good look for him. Making matters much worse, initial reports indicated that the “controlled substance” found by police was ecstasy tablets, but now rumors are swirling that the substance was in fact methamphetamines. Once again, not a good look.

This is a huge problem for T.I., on multiple levels. Clearly, his freedom is now in serious jeopardy, and unless his lawyers have some ace up their sleeves, I’m thinking T.I. might be screwed. But as far as his career goes, Tip has a ton of explaining to do. After being so lucky with his previous arrest, and getting off so easy (at least compared to other similarly charged individuals), to get arrested again only seven months after being released is not only idiotic, but it comes off as incredibly arrogant. If you were at one time facing steep federal gun charges that should have landed you in prison for ten years, but you lucked out with a relatively mild plea deal (thus saving your career from certain doom), would you drive around L.A. in a Maybach, smoking blunts? Even if the “controlled substance,” meth or otherwise, didn’t belong to you, and even if you don’t do drugs, would you drive around in that Maybach with people who do? Would you take that risk?

I sincerely hope not.

And this brings me to one of many reasons why Jay-Z is clearly the greatest rapper of his generation. Both T.I. and Jay-Z are former drug dealers who grew up in the hood, and have had tenuous relationships with the law. But the key to Jay-Z’s continued success is his commitment to making the transition from that life to the one he currently enjoys. The last time Jay-Z was arrested was in 1999 (for no less than stabbing a bootlegger), and since then dude probably hasn’t even gotten a parking ticket. He realized that drugs, guns, gangsters and jail don’t mix with boardrooms, sold-out arena tours and Beyonce. So he hired a driver and some security, cut negative people out of his life, and married Beyonce. The haters continue to hate, and Jay-Z continues to make bank and live the good life. Problem solved.

So take some notes and get your shit together, T.I. Every emcee in the game aspires to Jay-Z’s success. They study the way he rhymes and they study the way he does business, but no one studies the way he lives. Success and chronic criminality do not mix. Don’t believe me? Just ask DMX. Listen to It’s Dark and Hell Is Hot the next time you want to throw a middle finger to the law, and think of what might have been.

Smarten up, Tip.