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

August 14, 2025 | FlaglerLive | 4 Comments

Michael Gilbert in court. (© FlaglerLive)
Michael Gilbert in court. (© FlaglerLive)

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. 

Assistant State Attorney Jason Lewis runs the numbers. (© FlaglerLive)
Assistant State Attorney Jason Lewis runs the numbers. (© FlaglerLive)

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.

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Reader Interactions

Comments

  1. Skibum says

    August 14, 2025 at 4:00 pm

    This criminal made a bad decision for himself… one of many to be sure. But it doesn’t take a Sherlock Holmes to state the obvious: that if criminals made better decisions on a daily basis, they would not end up standing before a judge while dressed in an orange prison jumpsuit, awaiting their fate.

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  2. JimboXYZ says

    August 14, 2025 at 7:37 pm

    As the system keeps pulling him back into it, he may be just giving up as a “white flag of surrender” ? At this point, they’re talking to him in the courtroom like he’s getting great options for anything, like he’s in the room & not even there in the room. He’s become their incarcerated pet of sorts ? So he’s going to go with what’s behind door #1, Monty Hall cast of legal & justice types, the all expense paid stay at the state prison, 3 hots & a cot, the full on taxpayer route. Anyone that fears for their life, has to jump thru the probation hoops for conditions he can’t satisfy unless he wins the lottery & even there he’d have to cut a deal to leave the USA & it’s scope of authority to be free of that . When he called police, they stacked charges for nit picky things considering he was in fear for his life ? Maybe he’s done with making deals that suck without outright calling those judging him names or showing the courtroom disrespect ? He doesn’t care at this point what their deals or solutions are ? His quality of life is what it is ? Makes one wonder how much of the deal is more a matter or prosecution & defense going back to the budget that they have for the year, what is in the coffers for him being a profitable incarceration ? What is the optimal minimal cost, where there is a breakeven point on the bottom line ? Because the solutions are he pays someone for probation. Where he’s going inflation is irrelevant, he doesn’t have to grind, do the crappier work that he’ll never be self sufficient on his own. Sounds like they were almost begging/daring him to take their deal only to end up no better for it than what he has to deal with, when the next round of charges was the systems game in a game of life that he’s supposed to lose at ? I guess what I’m tying to say is, rejecting the deal makes no sense to those that have hope. He knows what prison life is, 15 years served that’s familiar routine, a lot got worse in just the last 4 years of Biden-Harris, probably is the next level of suck with Trump-Vance in the tariff era of USA economics of it all. Maybe he’s gotten to a point where he can appreciate the sun rising & setting, a quiet night in the mid 70’s as the moon cycles thru it’s phases. There’s fresh air to breathe, clean water, a simple life for a simple man, the rest of what goes on is a man made game that doesn’t matter. It’s ironic, we have Epstein Island, even Hunter Biden. They can’t put the one’s that are the criminals in that in prison, yet he buys a phone, buys a gun for relative protection and they’re stacking time on him. I think they’ll get what they want from him, he’ll take his chances surviving in prison vs attempting to avid becoming the same criminal or a worse one after serving an abbreviated sentence. In a way, he’s challenging them to commit to 20 years of expenses. In that regard has he actually beaten them ? Like a dog that lives 20 years, that’s the State’s commitment to not abuse & neglect him ? They want him to meet him at 4 years for this. He still faces Volusia County and they will stack more time on him for that. He already knows they will. Because that’s what the system does. In that regard, he’s a realist ? Are they looking for a prove it to them remorse in the compliance to take the plea deal that is never going to measure up to the remorse they want him to demonstrate in a courtroom for sentencing ? Whether that’s genuine enough or not for the deal makers by the deal breaker ? Leverages & power for deal terms ?

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  3. Sarah T says

    August 15, 2025 at 6:34 pm

    Only one gang or klan has stolen trillions of dollars and that’s the GOP!

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  4. joseph harley says

    August 16, 2025 at 1:53 pm

    @Sarah T… Amen!!!!

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