Why ASAP Rocky’s Bold Gamble Paid Off Big

ASAP Rocky’s acquittal in his shooting trial on Tuesday was notable for many reasons, but perhaps most dramatic of all was that the rap star’s gamble—to go to trial at all, risking up to 24 years in prison, in the face of being offered a plea deal by the state—paid off.

At the beginning of Rocky’s trial, he confirmed that he turned down an offer of six months in prison, three years of probation, and a seven-year suspended sentence. His reasoning, according to TMZ (though neither Rocky himself nor his lawyer Joe Tacopina ever confirmed this directly), was that the deal would “effectively end his career because he would lose all of his endorsement contracts, including Gucci, Puma, the Met Gala and, most important, he would not be able to tour and his career would be over. They would have him under their thumb for over eight years.”

Now that the trial is over, it’s worth looking at why that deal was bad enough to make Rocky risk so much to avoid it.

The restrictions that come with probation

To begin with, it’s notable that Rocky’s reported reasoning had nothing to do with actual prison time. Instead, it was probation and a suspended sentence that were apparently the dealbreakers.

The deal would have meant a number of things. First, Rocky would have a felony conviction on his record. That could mean, depending on the details, a loss of voting rights and a ban on owning firearms. There are other potential downsides that are unlikely to affect someone in Rocky’s position directly, like employment restrictions.

More directly, there’s years of probation, with seven years in prison hanging over his head if he violates any conditions.

Those conditions deserve a closer look. Back in November, we spoke to Erin Haney of REFORM Alliance about probation, and how it could affect the life of a hip-hop performer—in that case, Young Thug.

She noted that “one of the general conditions [of probation] for people is that they cannot usually leave even the county, but definitely the state, without explicit permission from their supervision officer.” While that could, on a case-by-case basis, be modified or negotiated (as it was with Thug), there’s no guarantee that would have happened with Rocky. Travel restrictions would make promoting his long-delayed new album effectively impossible.

Probation also often comes with restrictions on who you can spend time with. Often included in the list of prohibited folks are convicted felons or gang members. In Thugger’s case, he can’t be around a “member or associate of a criminal street gang,” with the exception of his brother and Gunna.

What exactly qualifies as a member or associate of a gang is vague, Haney said, and may even change from judge to judge.

Rocky, if he took the deal, might face seven years in prison just for being around, say, Lil Wayne or T.I. (both of whom have felony convictions) without getting permission from a probation officer first.

Haney worried about this with regards to Young Thug.

“If he cannot so much as collaborate on a song with or be at a concert with another artist who has a felony conviction,...that would be incredibly difficult,” she said.

In addition, probation frequently comes with restrictions on drug and alcohol use, even if the crime has nothing to do with intoxicants at all. That might have put Rocky in a position of risking prison time just for promoting his own whisky.

Yet another complication around drugs and alcohol is that frequently, people on probation are ordered to undergo drug screening. In many cases, Haney told us, people get tripped up not even by testing positive, but because they can’t make it to a test in the first place.

“In order to do that, you often have to miss work,” she explained. “In 2019, more prison admissions were for supervision violations than for new crime, and a good chunk of those were drug related, and really minor. We're not talking about new drug crimes. We’re usually talking about missing a test [or a] dirty test. Very minor violations. What I think that ends up serving as, is another way to catch someone. It’s another way to trip someone up.”

That, really, is the larger point. Probation is littered with potential violations, for both high-profile and everyday people. To get an idea of just how egregious this can get, look no farther than the case that inspired the creation of REFORM Alliance in the first place, Meek Mill. Meek’s case made news back in 2017 when he was sentenced to 2-4 years in prison for violating probation. Those violations were a series of low-level offenses, actual or alleged—positive drug tests, failure to abide by travel restrictions, and even a now-infamous arrest for popping a wheelie on a dirtbike.

Why ASAP Rocky rolled the dice at trial

It is certainly plausible to imagine a high-profile figure like Rocky, who causes big crowds almost everywhere he goes, especially when he’s with his even higher-profile partner, ending up in a fight (another of Meek’s violations); or on IG Live with someone authorities believe to be a gang member; or appearing onstage with a convicted felon. Any of these small slip-ups may have, under the terms of his deal, sent him to prison for seven years.

It’s understandable, then, why he chose to roll the dice at trial. Prosecutors ultimately decided they would recommend an 8-10 sentence if he was convicted. The difference between that and having the threat of almost that long a sentence hanging over your head every day for years, if you make a minor or even unknowing slip-up, may not have been all that great—especially when you figure in the almost certain loss of endorsements from companies and institutions that wouldn’t want to associate with someone convicted of assault with a semiautomatic firearm.

At the root of Rocky’s decision to turn down the plea deal, if TMZ’s source is to be believed, is a significant problem with the probation system as a whole — it exists largely to trip people up, rather than to ensure public safety or to help the people in it.

“We've gotten so focused and addicted, to punishment and incarceration that it's easy to forget the basis of supervision and probation, why it existed in the first place, which was to serve as an alternative,” Haney told us. “[It was supposed] to serve as support and services for people so that they could remain a valued part of the community that was contributing a way to make the community safer. Instead, we've gotten so attached to finding ways to catch people and lock them up every chance we get.”