Ex-Gang Member Michael Gilbert Back in Prison for 5 Years, Risking Another 5 Rather Than Settle

Sometimes, defendants’ self-defeating math puzzles everyone in court, prosecutors and judges included. But the defendants’ misfortune is not entirely of their own doing, especially when they are on probation, a system as if cynically designed to make probationers fail. Michael D’Angelo Gilbert is one such defendant. 

This morning Gilbert pleaded to a 20-year prison sentence on a probation violation that really amounts to a little over five years, because he’s already served almost 15. 

But Gilbert turned down a so-called “global” offer to serve just four years, and to resolve a separate case in Volusia County at the same time. The fairness of the case is dubious, and it appears more malicious than Gilbert’s alleged crime: prosecutors are pursuing him for a failure to register as a sex offender, after Gilbert himself alerted police to his whereabouts. 

That aside, Gilbert wants to fight the charges in Volusia County (though he’s offered to serve two years for them), even though, if convicted, he faces up to nine years in prison which would at least double the sentence he pleaded to this morning. It would triple it if the Volusia judge decides that Gilbert should serve the two sentences consecutively. 

It made no sense to Assistant State Attorney Jason Lewis. It made no sense to Circuit Judge Dawn Nichols. But there stood Gilbert, refusing a deal that would have guaranteed much less of the time he now risks serving. 

“Mr. Lewis, you know me very well. My decision is made,” Gilbert said. 

Lewis did know him very well. Still does. The two go back decades. Gilbert is not yet 39. He’ll mark that latest of so many birthdays in prison next week. When he was 18, he was convicted and sentenced to house arrest on a molestation charge involving a young teen. He violated his community control and was sentenced to his first prison stint. He was designated a sex offender, a designation he contested as recently as 2023. 

Soon after his release in 2007 he got involved with Brandon Washington, the ex-Bloods gang leader now serving a life sentence on a conviction for home invasion, murder, racketeering conspiracy and other charges. Gilbert cooperated with authorities to get Washington convicted (hence the fear he lives with every day). 

Specifically, he cooperated with Lewis. Though part of Washington’s gang, he was convicted on lesser charges, including possession of a firearm by a convicted felon and drug charges, and sentenced to 15 years in prison. Between credit for time served in local jails and “gain time,” or time off for good behavior, he completed the prison portion of his sentence in June 2021. He still had to serve 10 years on probation. 

Last September 12, after moving to the Bird’s Nest hotel in Daytona Beach, he called police, afraid for his life. He told police that he was an ex-gang member. When police showed up, they arrested him for failing to register his new phone number–the number he’d used to call police– as sex offenders are required to do, and to update his driver’s license, though he had registered his new address with police, and had bought the phone just two days earlier. 

He ended up with three counts of failure to register as a sex offender, each a third-degree felony, each punishable by up to five years in prison. Because he was charged with new crimes, and in the snowball effect of self-perpetuating offenses in the judicial system, it registered as a probation violation in Flagler County. His 2008 and 2009 cases were reopened. That’s what brought Gilbert to court last week and again this morning. If he had a chip on his shoulder, he hadn’t entirely put it there himself. 

It was now time to resolve it all, and Lewis was making the offer. He first did so in a hearing last week, and did so again today, as Gilbert was undecided last week. Gilbert had no interest in contesting the settlement in Flagler–especially since Lewis would have asked for 30 years in prison had he done so–but he was insistent on fighting his case in Volusia. 

“Just so he understands,” Lewis said, if he is convicted in Volusia County, “he scores like nine or 10 years in prison, and he only has credit for like nine months there. So I just want you to understand, if you go down there, you could wind up doing another nine or 10 years on top of what we have here. So I don’t know if you want to think about that with Miss Davison–I know you have–but I just don’t want you to get burned and wind up doing another 10 years in prison on top of here.”

Courtney Davison was the assistant public defender representing Gilbert. He would not budget on the Volusia case. He was willing to plead to the Flagler cases. 

“I would be willing to do 20 years with the credit for the 14.76 in, so that just this case alone, basically, would you doing about five years,” the judge told him. “If you want to do that, to get this case resolved, and you can go fight what you want to fight in Volusia, have at it. But what Mr. Lewis has offered you is four years to resolve them all. But I’m just here for Flagler, and if that means that much to you to contest that case in Volusia, I don’t have a problem with it.” 

Lewis said he had “everyone on board to do it with the four years,” including those overseeing the case in Volusia–except for Gilbert. Lewis was willing to reduce the three charges of sex offender registration down to one. 

“Wow, you do a lot less time by taking Mr. Lewis’s offer than mine,” the judge said. 

Gilbert said no. He pleaded to the Flagler probation violation, was sentenced officially to 20 years, with credit for almost 15. He was hoping to serve his time at the Volusia County jail pending the disposition of that case and before he is shipped back to prison, as that would give his mother, who is ailing, a chance to see him. But the judge said he may not get his wish: the state prison system is likely to claim him, and bring him back to Volusia County only for court dates.