To plead or not to plead, that is the question George Zimmerman is going to have to struggle with in the coming weeks and months as he lies in his rack looking up at the fly droppings on the ceiling of a 67-square-foot cell. Of course he might make bail, but that’s highly unlikely, especially after he gave his own lawyers the slip before turning himself in. And prosecutors knows that accused individuals who have to fight their cases while confined are a lot less likely to win than someone fighting from the streets.

Only the hardest of seasoned convicts would be able to reason through a decision of such monumental impact on their life without breaking out in a stone-cold sweat, and isolation certainly doesn’t help the process. At this point even his visitation privileges are being kept under wraps, but no matter how many visitors he gets (or how often is lawyer comes to see him, which won’t be all that often) Zimmerman’s going to be spending some long nights alone, with a million different scenarios playing out in his head over and over again. I’ve been there, done that—never with the kind of time this dude is facing staring me in the face like a double-barreled shotgun, but having some clammy moments nonetheless.

Sure, it’s easy for macho Stand Your Ground supporters and tough-talking bloggers to encourage Zimmerman to man up and take his case all the way to trial—it’s not their asses on the line, facing what could be 30 years in a Southern prison if the verdict comes back guilty.

Even with the best legal advice, which Zimmerman now seems to have in the person of Mark O’Mara, the decision is not going to be an easy one. This is not to say the legal team of Craig Sonner and Hal Uhrig (that dropped him like he was on fire at a very public press conference) are not first rate, they are; but they also are pitbulls who realized the media attention focused on the case would have made them household names—which it turn might have made them less eager to convince their client to cop a plea. They wouldn’t want the hot glare of the media to go away, as attested to by how long they answered questions at their press conference. O’Mara was commenting on the case for television before he took it for himself.

When all is said and done, whatever lawyer represents him, that mouthpiece will go home to his own bed after the case is over—but Zimmerman might not. He is going to have to step the number off all by himself if he loses, and a lonely existence it will be. There are a lot of prisoners in America wailing about the bad deal their lawyers talked them into taking.

Currently Zimmerman is being held in what’s known as "administrative segregation," or whatever they call it at the Polk Correctional Facility where he’s being housed. A bit of solitude can be soothing, but after protracted periods lack of regular basic human contact plays tricks on the mind. Even if one of the hacks, or the occasional trustee who’s pushing the food cart three times a day, recognizes his existence and briefly speaks to him, it’s not like the sense of community all human beings need to maintain their sanity. After serving three months in isolation, I discovered deprivation is a real bitch—and I knew that the maximum sentence I was looking at was a deuce.

If Zimmerman rolls the dice and loses, he’ll face years of such solitude since he won’t be allowed in the general population of any prison he’s sent to for years. Just his presence on the prison yard could cause rioting as black convicts sought to take him out and skinheads aimed to protect him as one of their own, or at least their enemy’s enemy. The one place in America where segregation might make sense is in penal institutions—one for whites, one for blacks, and one for Hispanics.

Nonetheless I don’t think it’s going to come down to that. When Zimmerman made his first appearance in court his eyes were as big as dinner plates; this ain’t no tough guy.The only courage this dude has shown he possesses was pistol courage. I expect him to fold like a house of cards when crunch time comes, and I don’t blame him.

Sure, the media would just love for the case to go on forever—it’s a ratings bonanza. But when Zimmerman’s offered a deal whereby he can plead to a lower manslaughter charge and be out sometime well within this decade, go on to write a book and make millions while becoming a NRA hero, expect him to take it.