Bill Cosby's Sentencing: How We Got Here, What His Punishment Could Be

Bill Cosby will walk into a Pennsylvania courthouse Monday and face the judge who has presided over the world-famous comedian's sexual assault case for nearly three years. The sentencing hearing may conclude with Cosby losing his freedom for the rest of his life.

More than 60 women have accused Cosby of sexual misconduct spanning decades — including one who came forward to WHYY — but it was the testimony of one woman, Andrea Constand, who twice confronted the comedian in court over how he drugged and molested her in 2004, that helped convince a jury during Cosby's second trial in April that he was guilty of three counts of aggravated indecent assault. With the convictions now locked into place, Constand's testimony may just be what will send Cosby to a prison cell. Cosby's attorneys are expected to appeal.

For the past five months, the comedian has lived in his mansion in suburban Philadelphia, outfitted with an ankle monitor. It is the same place a jury found he drugged, then sexually assaulted Constand, the only Cosby accuser whose case triggered criminal charges.

The judge has set aside two days for the sentencing proceeding, yet it is unclear how long it will take both sides to get through various witnesses, including psychologists and those who will vouch for Cosby's character and the reading of a victim impact statement. Prosecutors wanted to bring in some of the dozens of women who have lodged sexual misconduct accusations against Cosby to testify, similar to the sentencing hearing of former gymnastics doctor Larry Nassar. That will not happen, though. The judge in Monday's hearing blocked additional Cosby accusers from participating.

This day has been long awaited by Cosby's scores of accusers, many of whom filled the Montgomery County Courthouse during the 81-year-old's two trials to show support for Constand.

"This is certainly justice delayed, but it's not justice denied," said Deborah Tuerkheimer, a former sex crimes prosecutor and law professor at Northwestern University. "Everybody will be watching. Everyone will want to know if Cosby is given a pass after all this. If the answer is no, that's a message that will reverberate."

What will Cosby's punishment be?

Judge Steven O'Neill has a wide range of options. He could give Cosby house arrest or probation. If O'Neill deems that incarceration is appropriate, it could be anywhere from 10 months to four years behind bars, according to Pennsylvania's sentencing guidelines. But state law allows O'Neill to go far beyond the guidelines and send Cosby away for decades.

Cosby is 81 years old and legally blind, his lawyers say. It might not take a severe sentence for the punishment to mean Cosby's freedom will be permanently stripped away, said David Harris, a law professor at the University of Pittsburgh.

"Even a term of a few years could be the equivalent of a life sentence for Cosby," Harris said. "It would not be fair or just to fail to sentence Cosby to any time in prison given the amount of damage he did to these women and the very cynical and dangerous way that he accomplished these sexual assaults. It's just wrong."

Yet Cosby's defense lawyers are expected to underscore Cosby's age, his philanthropy, and his lack of a criminal record. In such a feeble state, Cosby's lawyers will likely say, how would he pose a threat to anyone else?

O'Neill will be weighing all of this, in addition to what kind of deterrent message the punishment will send and to what degree Cosby has shown remorse.

If Cosby is sentenced to jail, when will it start?

If O'Neill orders incarceration for Cosby, there is a chance he will be handcuffed and led directly into a prison cell. Any sentence over two years will be served in a state prison, while any sentence less than two years would send Cosby to a Montgomery County jail.

If he is sentenced to incarceration, Cosby's lawyers are expected to ask that the entertainer be released on bail while he fights his conviction on appeal.

Since Cosby has been on house arrest for five months, court watchers say the argument that he needs time to get his affairs in order would not likely gain traction with the judge.

But legal experts are split on whether O'Neill would let Cosby delay starting his punishment for another reason while he appeals. Some say that given his age and otherwise clean criminal record, being released on bail seems likely, though others are not so sure.

"The #MeToo movement is alive and well right now, so for a judge to allow him to stay out on bail after it was so difficult for prosecutors to convict him, I think it would be a slap in the face to the movement, and I don't think the judge is prepared to do that," said longtime Philadelphia criminal defense lawyer Chuck Peruto.

Harris at the University of Pittsburgh agreed.

"I don't see the judge granting an appeal bond that could stretch on for years because that could practically mean that the sentencing could be delayed long enough that he might never go to prison, and that simply cannot be what the judge has in mind here," Harris said.

How might Cosby appeal?

In Pennsylvania, someone has to be sentenced before appealing a conviction. And no matter what befalls Cosby, you can expect an appeal.

Legal watchers say Cosby's lawyers could argue that allowing five additional accusers to take the stand biased the jury against the entertainer. It was a controversial move since the women testified to alleged incidents for which Cosby was not on trial. Still, prosecutors pushed for the witnesses, hoping they would show the jury that Cosby had a "sadistic sexual script" of drugging and molesting women over many decades. The witnesses, including supermodel Janice Dickinson, provided some of the most emotional and dramatic scenes of the second trial. Another grounds for appeal is likely to center on whether portions of a deposition Cosby sat down for in a separate civil case was improperly admitted into the criminal trial, arguing that Cosby did not know the statements — including that he obtained Quaaludes with the express purpose of giving them to women he wanted to seduce — would eventually be used against him. He thought his admissions were confidential, Cosby's lawyers could argue, and so, his right against self-incrimination was violated.

If O'Neill find these or other appeal issues convincing, experts say the judge is more likely to release Cosby after handing down his sentence.

But another issue raised by court watchers is how Cosby's defense team and public relations representatives have repeatedly attacked the judge himself. Cosby's attorneys have tried multiple times to get O'Neill booted from the case. Camille Cosby has disparaged O'Neill and released a blistering statement following her husband's conviction alleging that O'Neill's court did not give the comedian a fair shake, saying it was instead "mob justice."

Defense attorney Peruto said while lashing out at the judge is not something that will be formally considered, it is difficult to imagine that O'Neill would forget it.

"The judge is a person. He's a human being," Peruto said. "Anyone who thinks he's not affected by that is crazy. Will he say it? No. Will he admit it? No. Is it going to be a factor? Of course it is."

Yet Harris said being magnanimous about casting aside personal feelings is part of the job of being a judge, and he does not think O'Neill's punishment will at all be affected by the scorched earth tactics pursued by the Cosby team.

"We depend on judges to ignore many things over the course of a trial. To put it out of their minds, as much as a human being can do," Harris said. "He will likely just operate on the facts and the law. I can't imagine O'Neill acting out of emotion and anger."

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