How Much Time Will Diddy Get? An Investigation

Now that the verdict in Sean "Diddy" Combs' federal criminal trial has come down, the main thing that's left for the mogul is his sentencing. He was found guilty on two counts of transportation to engage in prostitution. But how much time, if any, will he serve in prison?

The sentencing phase of many federal cases gives judges an enormous amount of discretion. In this case, Judge Arun Subramanian (the recipient of Diddy's "You're doing an excellent job" compliment) can sentence Combs to anything between time served—which would mean the Bad Boy head would walk out a free man—and 20 years behind bars, which is the maximum allowed by law.

In advance of his sentencing on October 3, here's a rundown of all of the factors that weigh into that question, as well as estimates from a few experts.

The importance of guidelines

For about two decades, from 1984 until 2005, judges barely had any discretion in sentencing at all in federal criminal cases. There was a set of mandatory guidelines: a narrow range of punishment, within a handful of months, based on a few factors: the type of crime and the criminal history of the defendant.

Then came United States v. Booker, a 2005 Supreme Court case that changed those guideline ranges from mandatory to advisory. Since then, judges have to take the guideline range into account, but they no longer have to abide by it. They can give sentences that are longer or shorter.

How the guidelines work

How the system operates is this: there is a sentencing table, which you can see here. There are two factors in figuring out an offender's possible sentence: the offense level (a number assigned to the crime, between 1 and 43—the higher the number, the more serious the offense); and your criminal history (divided into six categories, from least to most serious). You look on the chart at the intersection of those two numbers, and the guideline range (listed in months, as is customary in federal cases) is there.

But here's where things get tricky: that first number, the offense level, can have a bunch of complicating factors in addition to the actual crime. There are a number of elaborate ways for attorneys to argue that number higher or lower.

Because of this, figuring out the guideline range in Diddy's case turns out to be surprisingly complicated. The government and the defense have very different takes on it. They both agree that his criminal history, the second factor, is the lowest it can be, in category 1. But they have wildly disparate ideas about the offense level.

The difference between 24 and 16

Both sides agree on a starting place: 14. That is, they both say that what is called the "base offense level"—the number attached to the crime itself, before any complicating factors—is 14. That, combined with Diddy's lowest-possible criminal history score, would mean a suggested sentence of 15-21 months.

However, that's not where either side winds up. Diddy's lawyers end up going just slightly higher, for technical reasons. But the government is another story.

"It seems like the prosecution's throwing in the kitchen sink," explains legal analyst and former trial attorney Terri Austin, who covered Combs' trial. "[They're] adding as much as they possibly can."

So what's in this kitchen sink, exactly? The feds say that three levels should be added because Combs was a "manager or supervisor," and the criminal activity was "extensive." [For those of you playing along at home, that's from section 3B1.1 of the sentencing guidelines.] Then they say another two levels should be added because Combs "willfully obstructed or impeded, or attempted to obstruct or impede" the investigation and prosecution of his crimes.

Most controversially, at least to Austin, is that the government argues there should be an additional five-level leap because there were more than six victims. How do they get that, when only Cassie Ventura and Jane Doe were mentioned specifically in the charges? Because, they say, seven of the escorts involved in Combs' freak-offs also count as victims.

Austin is unconvinced by this argument.

"No one ever argued during the case that these escorts were victims," she says.

When you put all those add-ons together, Combs' offense level moves from 14 to 24, which means that, according to the government, his guideline range is between 51 and 63 months' imprisonment.

The defense ignores all of this. They say, essentially, that because there were two victims (Cassie and Jane), an additional two levels need to be added to the 14 starting place. And...that's it. No obstruction, no escorts, no managerial claims. So they end up at 16—a number which, with Combs' non-existent criminal history, gives them a 21-to-27 month suggested sentence.

Complex reached out to Diddy's legal team to explain their reasoning. They responded only to say that their guideline range arguments "will be fully flushed out in sentencing papers."

Ultimately, it will be up to the judge to decide where the guideline range sits.

Splitting the baby

"He's probably going to pick a number somewhere between where the prosecution is asking, and the defense is asking."

That's Arick Fudali, an attorney at The Bloom Firm who has worked on many high-profile cases involving sexual assault. He currently represents two people suing Combs, a John Doe and former Danity Kane member Dawn Richard.

The lawyer is speculating—at Complex's prodding, to be clear—about what Judge Subramanian is likely to do.

"The judge has the discretion and the duty to pick to decide what sentencing is appropriate," Fudali continues. "So he can—this is a terrible metaphor—split the baby. The judge does have the discretion to pick a number in between [what the prosecution and the defense present]."

Austin agrees.

"The defense usually argues for the smallest amount under the guidelines, and the prosecution argues for the most," she says. "And then you come out somewhere in the middle. So I think that's what the judge will do."

But wait, there's more

Just when you thought things couldn't get more complicated, there's yet another thing to take into account. The guideline ranges are just that—guidelines. Judge Subramanian has the ability to go above or below them, though Austin points out that doing so might open his decision up to appeal issues.

In fact, before she was fired by the Justice Department, lead prosecutor Maureen Comey said that she intended to ask for Combs to receive an above-guidelines sentence. At the mogul's bond hearing, on the day of the verdict, she announced that she would seek the statutory maximum of 20 years.

As for going below the guideline range, whatever the judge decides it is? Austin is doubtful.

"Judges rarely go below the guidelines," she explains.

Are there clues?

Has Subramanian given any indication as to how he might rule? Complex posed this to both Austin and Fudali, and they both thought that how he presided over Combs' bond hearing might provide some clues to his thinking.

At that hearing, the judge said that part of the reason he was keeping Combs locked up until sentencing was his past violence. That violence, much of which his lawyers admitted during the trial, made Subramanian believe that the mogul could not prove that he wouldn't be a danger to anyone. The judge mentioned Combs had demonstrated "disregard for the rule of law and a propensity for violence."

"I do think looking at how the judge was leaning during the bail argument does give you some indication of what he's going to do in terms of the incarceration," Austin tells Complex.

Fudali agrees.

"I think that [the bond hearing] actually is a good clue as to what's important to him—that he is certainly considering the violence and what Mr. Combs' threat to society and to his prior victims actually is."

So maybe the judge is leaning towards the prosecution, and thus a longer sentence? Well, maybe not. After all, guideline ranges and propensity for future violence are only two possible factors that may factor into the judge's thinking.

"The judge can basically consider, or not consider, almost anything," Fudali says. "He reviews the evidence, the criminal history, personal impact [statements]—there's so many factors the judge can look at."

Even with all that, he says, he still expects the judge to "fall somewhere between the defense's and the prosecution's suggestion."

What a sentence could look like

By the time of his sentencing, Combs will have been in jail for just over a year. This is time that is likely to count towards his sentence, whatever it might be. In addition, for federal sentences of over a year, inmates in many cases have to serve only 85% of their time (this "good time credit" is a reason many fed sentences are a year and a day).

The math involved in this is surprisingly complicated, so coming up with an exact number is nearly impossible. But the general idea is that for each year of a sentence, the prisoner can, depending on behavior, programs they enroll in, and other factors, expect to spend around 319 days behind bars.

How might this apply to Sean Combs? Let's take an example of a 36-month sentence, which is in between the defense and prosecution's guideline ranges. He would almost definitely get credit for the 12 months he's already served. That leaves 24 months, or two years, of imprisonment. With the good time credit, he would probably end up serving somewhere in the 20-to-21 month range.

None of this is guaranteed, of course. The judge may set the guideline range wherever he decides is fair, ultimately go above or below it anyway, give credit for time served or not, and the 85% good time credit may or may not be applied, in whole or in part. In the end, the day of Sean Combs' release will be determined by the same man who presided over his criminal trial.