Cosby Guilty 14 Years After The Fact: Bars, Bankruptcy Or Both?

Guilty verdict carries a maximum 30-year sentence but 80-year-old comedian probably faces worse threat to his “essentially unlimited” personal fortune, with no way to rebuild.

Flight risk became a serious concern when the guilty verdict came down on Bill Cosby’s second sexual assault trial. While he doesn’t appear eager or willing to flee the country instead of accepting his fate, someone in a similar position might welcome assets stashed overseas and a way to get to them.

He’s got an estimated $100 million in potential wealth and access to private planes. That kind of money can buy a lot of refuge, especially if you’re not planning on living too long anyway.

But given the venom with which he pushed back on the suggestion that he might disappear before his sentencing, odds are good his advisors didn’t prepare him well enough to make it a viable option.

Besides, Cosby’s got enough to worry about here at home.

Running out the clock

Given the way the first trial ended without a unanimous jury decision, an appeal is practically inevitable. Cosby will probably pay additional bail to defer jail time until the process is exhausted.

That process could take four to five years at minimum, by which point he’d be 85 and, based on his deteriorating health and vision, in fairly fragile shape.

Even if the higher court affirms the guilty verdict, it’s still an open question whether someone in his condition will ever get a long prison sentence — assuming of course that he lives that long in the first place.

In the meantime, he could live an extremely quiet but relatively comfortable life under the equivalent of house arrest. Nobody seriously expects him to work again. He was already effectively retired, with his shows pulled from syndication and his number deleted from his agent’s call list.

It’s not especially glamorous or dignified, but every day at home beats a day in prison. Look for his lawyers to begin a campaign of endless delays as they work to give him time to take the mortality exit.

A question of assets

Of course fancy legal footwork costs money. He’s already out at least $675,000 in attorney bills defending himself from related civil suits and could be on the hook for at least $1 million in bail as long as he stays out of jail.

That’s not a trivial amount of money even if you’ve earned $100 million across a 50-year career. Apparently a vast chunk of that cash is sunk in Cosby’s New York townhouse, which he’s tried to borrow against to pay the lawyers.

At a guess, the property is worth $20 million. He paid under $6 million for it in 2006 — back in the boom years — and the bankers weren’t happy with the amount of debt already on the table. Either way, he tried to get $30 million out of the place, so the situation looks a little more desperate than anyone’s let on.

If you’ve got money to live on squirreled away elsewhere, just sell the house and pay the lawyers from the proceeds. Otherwise, you’ll just keep accruing $1 million in tax every year, plus the interest on the loans.

The problem there is that even if the building is beautiful, not a lot of people necessarily want to live in the house where he might easily have brought victims over the years.

We also know that he’s fought his home insurance carrier to get them to pick up his legal bills on the civil suits, based on the argument that if he caused injury to those women on the property, the policy has to pick up the costs.

The insurance company is appealing. He may never get that money back. And if the courts find that any of those women were unjustly defamed when he denied their accusations, he’s out millions more.

Even if he dies during the process, his estate is liable. From his point of view, the only good news there is that the statute of limitations on civil sexual suits expires a lot quicker than it does in criminal court. The cases he’s now facing are probably the only ones that made the deadline.

There’s also the question of why he doesn’t simply settle out of court like he did before. Based on his track record, $3 million to $4 million per litigant should get them off his back and let him drift back out of the headlines.  Multiply by 10 and it’s real money.

The criminal verdict going against him weighs heavy on those civil suits, where the burden of proof was never all that high to begin with. If he can find the cash, now is a good time to make an offer.

Bases uncovered

Add it up, it doesn’t look like the behavior of a man with mega-millions to burn. Maybe it’s a convincing act to conceal a huge asset protection trust, but I don’t think so. The desperation and the gloom feel a little too real.

Cosby has four living daughters and three grandkids to share his posterity. That $100 million could make a huge difference when it comes to paying their bills in perpetuity.

That’s where the advisors needed to focus from Day One. Because even if Cosby dies before the legal wheels stop grinding, his estate remains on the hook.

Of course if the bulk of the assets were rolled into an asset protection trust years ago, it wouldn’t be a problem.

Statutes of limitations are a huge factor in whether asset protection trusts succeed or fail. In Nevada, for example, a trust needs to be mature for 24 months before it’s ready to roll.

That means that Cosby would have needed to create a trust before 2003 in order to be shielded from the lawsuits that started sprouting in 2005. 

Unfortunately, he paid the woman who just beat him in criminal court $3.4 million in 2006. There would be zero rationale for that if all his liquid assets were already safe in a property seasoned trust — in that scenario, he could have simply let her lawyers bang futilely against his shield and file personal bankruptcy to defeat the judgment. 

But he didn’t. And with that fact on the timeline, it looks a lot less likely that any trust will help him now.

Cosby may end up going bankrupt after all. Not to cover the traces of a monster trust that will pass his fortune on to his family, but because his victims got there first.


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