Critics Say Judge Matthew Destry Gives Harsh or Random Sentences

Critics Say Judge Matthew Destry Gives Harsh or Random Sentences

Herb Smith, a lanky 23-year-old, drove a slick crimson Audi through the streets of Fort Lauderdale while a friend rode shotgun. At 4 p.m. last October 7, they caught a red light. A Broward County Sheriff's patrol car stopped beside them at the intersection. When the officer glanced over, he noted the Audi's pitch-black tinted windows — a noncriminal traffic infraction — and flipped on his strobes.

Smith knew he was screwed.

The officer made his way to the driver's-side window. Smith leaped into the back seat to act as if he hadn't been driving. When the officer peeked in, Smith's feet were dangling haphazardly above the gearshift. In the mesh pocket behind the driver's seat, the officer noticed a magazine containing .40-caliber ammo.

In 2012, Smith had racked up nine felonies for grand theft, robbery, and burglary when he and some neighborhood friends went on a spree of break-ins and carjackings. Circuit Court Judge Matthew Destry, a stoic, white-haired 54-year-old, could have sentenced Smith as an adult to 80 years in prison but agreed to treat him as a youthful offender — common with nonviolent offenders up to age 21 — and gave him two years in prison. Smith was released in June 2014 but had to complete four years of probation. His probation dictated that he not possess guns or ammunition. Then, after he racked up a series of traffic citations in 2015, Smith's license was suspended when he failed to appear in traffic court and pay fines.

Last November 24, several weeks after being stopped in the Audi, Smith returned to Destry's courtroom for a revocation-of-probation hearing.

Supporting him in the courtroom was Ratonya Dumas, a warm, middle-aged woman who considered Smith like a son since he had dated her daughter. "He's a sweet kid who had a hard life," she says. "His father was in and out of prison, and his grandmother raised him."

Florida's criminal punishment code requires judges to fill out a score sheet to determine a fair sentence. Each criminal charge carries a certain number of points and correlates to a recommended sentencing range. When Smith's charges were tallied, including the probation violation, the possible sentence was 13 to 85 years.

Shortly after Smith was arrested, the prosecution offered Smith a plea deal for 13 years for the revocation of probation — the lowest they could offer based on the guidelines.

Brian Greenwald, Smith's disheveled private criminal attorney, figured that any judge would be lenient on the young man, understand it was a stupid mistake, grant a downward departure from the recommended sentence, and send him to prison for the remainder of his probation term: two years. After all, driving on a suspended license and possessing ammo are minor, nonviolent offenses. Despite his client's long rap sheet, Greenwald insists Smith has never hurt anyone.

Then again, prior to going into private practice, Green­wald had served as a public defender for eight years, representing poor, indigent people accused of crimes. Over the course of trying more than 150 cases, he had witnessed Destry develop a reputation for handing out harsh or surprising sentences.

Down came Smith's sentence: 60 years in prison — more than four times the prosecution's recommendation. That's more than half a century. It's almost three of Smith's lifetimes. A 2075 release. Because Florida law requires that inmates serve 85 percent of their sentences, with credit for time already served, the earliest Smith could be released was in 48 years. He'd be 71 years old.

"Nobody saw it coming. I thought I heard it wrong. I looked back and everyone in the court had their jaws on the floor," Greenwald says. "It was like watching a car wreck in slow motion."

Dumas almost fainted when she heard the sentence. "I've seen murderers and rapists get less," Dumas says. The night of Smith's sentencing, Dumas went home and launched an online petition calling for Destry to be removed from the bench. More than 23,000 people eventually signed it.

On December 1, news broke of Destry's harsh sentence. Greenwald then made a motion to reduce it, and at a hearing on December 10, Destry shocked everyone again: He let Smith go home that day with no prison time but a 15-year probation.

"When Destry read the sentence, it took everyone a minute to realize what he had just said," Greenwald says. "We were expecting 13 years [in prison] or something. It took a minute to register that Herb was going home."

Though people describe him as a likable guy personally, Destry has handed down extremely harsh or extremely random sentences, frustrating both the attorneys who appear before him and the defendants who seek his mercy. In a county notorious for its wacky judges, Destry has also been criticized for tweeting from the bench, arriving hours late to court in the mornings, and holding sessions until midnight. The spotlight on Destry highlights the fact that once they are in office, it's hard to evaluate judges objectively, and they operate with little supervision. Last year, an appeals court overturned 11 of Destry's decisions. But recently, his wild seesawing has been jeopardizing his seat, which is up for reelection this November.

Broward public defender Howard Finkelstein believes that in Smith's case, Destry cowed before the bad publicity: "Destry did the right thing but for the wrong reasons. To go from 60 years in prison to being released that day — the takeaway is that justice is random in Broward County."

At times, Judge Matthew Destry has handed down sentences longer than prosecutors had sought.
At times, Judge Matthew Destry has handed down sentences longer than prosecutors had sought.
Photo by

In a Broward courtroom at 10:30 a.m. January 28, a middle-aged black man in a blue T-shirt and bright-red cargo shorts stood before Destry. The man twitched anxiously. His eyes were opened wide. To his left, his public defender, Joe Burke, flipped through papers, trying to set a next court date. But before he could, the man piped up out of turn.

"I know my rights. I know I can have a fast and speedy trial," he blurted out. "I want that."

Mortified, the public defender looked up and whispered to his client in a desperate attempt to calm him. The client shoved him aside.

"I'm tired of this thing dragging out! I want it taken care of today. Today! I want to represent myself."

The public defender argued that his client suffered from mental illness. Clearly, he couldn't represent himself.

"I've read books," the man countered. "I know the law."

Destry leaned in, eyeing the defendant. "If you want to represent yourself, I'm going to have to determine if you really do understand the law. Come back at 1:30 for a pro se hearing."

"But judge — ," the public defender pleaded.

Destry called the next case.

In the back pew, two female defendants who seemed familiar with Destry whispered among themselves. "Yeah right, he's going to come back at 1:30, be in jail by 2," one of them said. Both women erupted in laughter.

Destry did not return multiple requests for comment from New Times, but other news outlets have reported that he grew up in Montreal and can speak and write in French. He's a music aficionado and hates the jarring sound of cheap speakers. He's even been known to bring his own to parties.

After graduating high school, Destry joined the Air Force and was trained to be a Russian linguist. Then he settled along the west coast of Florida and attended the University of Tampa. He graduated from Stetson University's College of Law in 1991.

Destry worked as a prosecutor in Pasco County, north of Tampa, then a little farther south, in Pinellas County. In 1993, he helped prosecute the high-profile case of Aileen Wournos, America's first female serial killer. Charlize Theron starred as Wournos in Monster, a feature film about her life. The highway prostitute had confessed to murdering six men. Destry was praised in the media for his work on the case.

Soon after, Destry moved to Fort Lauderdale. In 2002, he married a saleswoman named Laurel. Destry worked in private practice, mostly handling racketeering and white-collar fraud cases, then joined the Attorney General's Office under Charlie Crist. In 2006, Crist was elected governor.

Over the years, Broward had been developing a reputation for wild judges. In 2001, a judge was found drunk and naked from the waist down during a judicial conference. In 2007, Judge Lawrence Korda was found smoking pot in a public park. Also that year, Judge Larry Seidlin presided over hearings related to the death of model Anna Nicole Smith. Seidlin called a blond attorney "beautiful," took calls from his wife in court, and would cry awkwardly on the dais when he thought about Smith's death and funeral. After the case, Seidlin was offered interviews and TV shows. He mailed Crist his resignation that June.

Destry applied for the judgeship. Crist gave him the seat that November.

"I just stepped up to the plate with the best that I had and am tremendously honored to have been chosen," Destry told the Sun Sentinel after his appointment.

Greenwald remembers that the public defenders "figured he'd have a state slant, since he was a former prosecutor. Other than that, we thought he was going to be just like any other judge."

But soon, say several current and former public defenders, they began noticing that Destry handed out long sentences to poor defendants, even for nonviolent crimes like theft and burglary. He developed a reputation as a "hanging judge" — an unusually harsh one. In some cases, he gave defendants sentences that were longer than even the prosecution had recommended. In 2014, he sentenced a first-time drug offender to ten years in prison — more than six times the prosecution's 18-month offer in a plea deal.

"It was almost like he was punishing people for going to court and wasting his time," says Finkelstein, Broward's public defender. "That's their right if they want to do that, but Destry's a bully."

As a result, say several defense attorneys, even in cases where they believe their clients to be innocent and would normally recommend taking a chance at trial, they instead recommend that defendants almost always take plea deals if facing Destry.

"We try to insulate our clients from Destry and the wrath of a tyrannical judge," says Rafael Nones, a former Broward public defender who regularly appeared in Destry's court. "One or two years is better than decades being taken away."

As a prime example, they point to the case of Brian Dunlevy, a poor, homeless 27-year-old who was one of eight people arrested in a boiler-room scheme in 2011 in Fort Lauderdale. The perpetrators bilked more than $200,000 from investors by creating a phony alternative fuel company and selling nonexistent stock.

Dunlevy worked under Michelle Braun, a tall, curvy blond who had gained notoriety for running a high-class escort service in Southern California. Two years earlier, Braun had pleaded guilty to laundering money and transporting a woman across state lines.

She caught a break in Destry's courtroom, though. Braun — who had reportedly made $8.5 million with her escort service — cut a deal with prosecutors to pay more than $200,000 in restitution to the 20 victims who lost their money. She was able to avoid prison time, serving a year of community control and four years' probation.

Dunlevy, a scraggly white man who has been diagnosed with a mood disorder, PTSD, and cocaine addiction, wasn't as lucky. Like Braun, he was facing 95 years in Florida prison for identical charges related to organized fraud.

Dunlevy was never offered a plea deal. He couldn't afford to pay restitution like Braun had. Destry sentenced Dunlevy to 15 years in prison. He'd be released in 2026, when he was 42 years old. The other six codefendants quickly scrambled to raise restitution money, and all avoided prison time.

Five years later, the case still haunts Dunlevy's public defender, Jim Weick. Every year during the holidays, he writes Dunlevy a letter, letting him know that he still thinks about him.

"This is my worst case in my 20 years as an attorney simply because of how the others were sentenced," Weick says. "Sometimes I find myself thinking about Brian before I go to bed at night."

Then there is the flip side — cases in which Destry seemed eager to accept a state attorney's plea deal: In 2012, Destry sentenced a 20-year-old Brazilian man who pleaded guilty to raping a 15-year-old girl to only one year in jail. In 2015, Destry sentenced a man to ten years in prison after he had lied about the disappearance and murder of his 5-month-old son. A few months later, Destry accepted a plea of 20 years for a man who murdered his wife. In January, Destry sentenced a man who raped a middle-school girl to two and a half years.

"He is too stubborn, and there is no rhyme or reason to his sentencing," says an assistant state attorney who asked for anonymity. "There is so much mental stress in that courtroom because everything is so unpredictable. You never know what is going to happen."

Brian Greenwald has seen Destry earn a reputation for meting out harsh or surprising sentences.
Brian Greenwald has seen Destry earn a reputation for meting out harsh or surprising sentences.
Photo by

It was 10 p.m. on October 31, 2013, and witnesses were lined up in the courtroom hallway. Attorneys had started grumbling hours ago that Destry was not excusing them. Instead, Destry kept plowing through hearings even though it was late and everyone wanted to go home.

It didn't matter. Finally at 11 p.m., court was adjourned.

"Parents wanted to take their children trick-or-treating," says one woman who was there but asked for anonymity. "He thinks he's funny. I think he even made a joke about ordering Chinese."

Destry later defended his actions that night, saying he didn't want to tell people to come back on a later date. He stressed he was working too.

Justified or not, the attention on Destry's actions illustrates that it's difficult to measure judges in any objective way, and once in office, they have little supervision and wide latitude in the way they perform their jobs.

Destry's behavior draws mixed reviews. For instance, he rarely lets attorneys postpone cases so they can better prepare. But where some see that as frustrating, others say he is running a tight ship. He sometimes tweets from his courtroom ("Jury seated in State v John Spencer"). Some say the transparency is desperately needed in the criminal justice system, whereas others say it is another of Destry's eccentric ways.

In one instance, Destry allowed a prosecutor to serve as a juror. Defense attorneys were shocked, considering she worked in the same office as the prosecutor assigned to the case. According to a court transcript, Destry said, "I don't think that a person's occupation is a valid basis, if you will, for a cause challenge. I just don't see it that way. So just because she is an assistant state attorney or for that matter an attorney doesn't mean she can't be a good juror."

Even Destry's sentences that are seen as "harsh" by some might be characterized positively — as "tough on crime" — by others.

"You're never going to find someone lose an election for being tough on crime," Greenwald says.

In December 2014, Broward Beat reporter Buddy Nevins published an article about Destry titled "Broward Judge Labeled Arrogant and Rude." In it, lawyers criticized the judge for frequently arriving late to court and holding sessions late. They complained that Destry "has no understanding for other people's time" and "never gives the defendant a break."

Afterward, Destry met Nevins in his courtroom office that overlooks the downtown Fort Lauderdale sky rises and New River. Nevins noted on Destry's shelves the autobiography of Rolling Stones guitarist Keith Richards and a copy of Moby Dick.

"I know I'm out there," Destry told Nevins. "I'm the judge, and I get the criticism. The criticism is unfair."

Destry explained that he arrives an hour late to court to "give those in custody time to talk to their lawyers" and make plea deals. He told Nevins he would rake in more money in private practice — almost three times his $150,000 judge salary. He described his judgeship as a duty to the public.

"I would like people to say that Matt Destry was a good guy," he said, "that what I did here made a difference."

"Over the years, a lot of judges come across as arrogant, but he was not like that at all," Nevins recalls. "Some people are hurt by people not liking them, and I get the feeling Destry was less able to take that kind of criticism."

Wayne Spath runs a Brandy's Bail Bonds near the Broward County Courthouse. Every two years, he donates to a handful of judges he supports. Destry was one of his picks in the 2010 election.

"I think he's smart, nice, a good judge, and a friend," Spath says. "I've read a couple of things about him, but you have to take them on face value and look at each one individually."

Like Nevins, Bill Gelin, who runs the Justice Advocacy Association of Broward blog, has aired complaints about Destry. In 2014, he conducted a poll in the comments section. Commenters wrote that the judge "is a disaster, keeps people in jail for no reason, talks down to attorneys." Another wrote: "Destry fails in all categories listed and is possibly (and that's saying a lot when painting a picture of Broward judges) the worst judge sitting." Yet another said: "Who cares about a survey? Broward voters don't do anything about bad judges except reelect them. What's the point?"

From left: Demetrius Vidale, Maxime Cherilus, and Herbert Smith believe they were sentenced harshly by Destry.
From left: Demetrius Vidale, Maxime Cherilus, and Herbert Smith believe they were sentenced harshly by Destry.
Photos by Broward Sheriff's Office

It is voters who have the most power over judges — by electing them. Once in office, though, the judges have a lot of free rein and little supervision. At the county level, a chief judge has the authority to rotate judges to other divisions and step in when a judge is backlogged but cannot override another judge's opinion. People can also file complaints about judges with the state's Judicial Qualifications Commission, but those are not made public.

The Broward County Bar Association used to send surveys to Broward County attorneys to critique judges but hasn't since 2008.

"The fact is that without [the J.A.A.B. Blog], there would be no accountability among judges," Gelin says. "The Broward Bar doesn't do polling. Without polling, there's no accountability. My goal is to shine a light on this critically."

It's difficult to objectively measure a judge's performance. One way of comparing them is to look at cases in which a judge has ruled and a defendant then appealed to a higher court. Examining cases from 2015, Destry and Barbara McCarthy were the Broward Circuit criminal judges with the most cases overturned and remanded by the Fourth District Court of appeals — 11 each.

Repeatedly, the appeals court has stated that Destry fails to offer reasons for his decisions. Whenever one of Destry's rulings is overturned, there must be more proceedings, and in egregious instances, cases have to be tried again. This, says one prosecutor, means he "wasted the state's time" by handing down unjustified sentences. One public defender estimates it wastes thousands in taxpayer dollars.

In 2012, Kate Peacock had been found in possession of oxycodone and cocaine. Peacock accepted a plea deal that would have her serve one year in jail. She was supposed to surrender at her sentencing hearing. But Peacock, age 38, missed it. Her defense attorney explained that she was absent because she had tried to kill herself and was being treated in the hospital.

According to court records, Destry asked Peacock's attorney: "So it wasn't like someone else inflicted these wounds or prevented her from being here?"

Since Destry believed she missed court of her own accord, he invalidated Peacock's plea and sentenced her to ten years in prison. The appeals court ended up reversing Destry's sentence. "The trial court... simply assumed that a suicide attempt is, ipso facto, a voluntary act. Although a suicide attempt could be deemed voluntary in some circumstances, a suicide attempt could also be an involuntary product of mental illness. In this case, the plea colloquy confirmed that appellant had a history of mental health issues."

In December 2014, Stephanie Kraft, a 58-year-old former Broward School Board member, was looking at up to five years in prison after being found guilty of official misconduct. (She had helped a development project for which her husband was a consultant by putting it on a school board agenda and not disclosing her conflict of interest.) Destry put her in jail while she awaited sentencing. Kraft's lawyer balked, stressing that Kraft was a nonviolent offender and that her elderly mother was battling cancer and needed Kraft to take care of her.

The appeals court reversed Destry's decision in February 2015, calling it "arbitrary and capricious" and saying that "the court provided no reasoning." After the media reported on the matter, Destry changed Kraft's sentence to no jail time but five years' probation and 20 hours of community service.

"This man isn't changing," Green­wald says. "Herbert Smith was Stephanie Kraft all over again."

In January of this year, attorney Gary Kollin challenged Destry's decision to not seal the record of his client Edward Gotowala, who had been ordered to two years of probation in 2009 on theft and battery charges.

The appeals court asked Destry to provide reasons for denying the request. Destry said that sealing his criminal record would "pose a danger to the citizens of Broward County and the general public."

The appeals court reversed Destry's ruling because his reasons were "merely based on generalized considerations" and not a "good reason" to deny the order.

"He makes it impossible for these people to try to move on," Kollin says. "It's not just sealing records. It's like [Destry] has never understood what it's like to be poor and to need a job and go to work."

Ratonya Dumas launched an online petition calling for Destry to be removed from the bench.
Ratonya Dumas launched an online petition calling for Destry to be removed from the bench.
Photo courtesy of Ratonya Dumas

After Ratonya Dumas uploaded her petition calling for Destry to be removed from the bench, the calls and emails started rolling in. In a week, her inbox was flooded from families who had been touched by Destry's sentences and wanted to commiserate — and see if any action could be taken against him.

Paula Vidale reached out to explain that four years ago, when her son Demetrius was 19, he had hurled a rock at a bus in Broward County. Paula felt he needed to face the consequences of his actions and turned him in. He was charged with throwing a deadly missile and criminal mischief and placed on probation by Destry as a youthful offender. Then, last year, Vidale was linked to a grand theft. That charge was overturned because of lack of evidence, but it was still considered a breach of his probation. Destry sentenced the 22-year-old to 20 years in prison.

Last summer, the appeals court decided that Destry had revoked Vidale's probation and sentenced him on hearsay, not actual evidence. In the meantime, Vidale sits in prison waiting for a new trial.

"I am not afraid to say when my son is wrong. I was the one who turned him in and started this," Paula says now. But "this mess is because of Destry. Your life can be ruined depending on what day you catch him on."

In 2012, Maxime Cherilus was juggling two jobs to make ends meet and had to drop out of college. He was studying business administration and wanted to open his own company one day. The problem was that Cherilus had only $1.13 in his bank account, and his $500 rent payment was past due. He says that's what led him to deal $50 worth of crack cocaine to an undercover Coral Springs Police officer. He was 22 years old and had never been in trouble with the law — but as a Haitian immigrant, he feared deportation if he took the prosecution's 18-month plea deal. So he took his chances and went to trial.

On the morning the trial began in 2014, Cherilus stopped by the home of his big brother, 42-year-old real-estate agent Rica Danastor, and asked to borrow one of his suits for court. "He was happy," Danastor recalls. "He told me, 'This is my last day in court and everything will be cleared.' "

Except it wasn't. He was convicted, and Destry sentenced him to ten years in prison — more than six times what the prosecution had offered in the plea deal. His release is listed as February 2024. Cherilus will be 34 years old.

"This is one case in my over 18 years of practice that I can't wrap my head around," his attorney, Michael Weinstein, says now. "I'm not saying that Max didn't deserve to be punished, but with that sentence — ten years — you're taking away all of his good years. It's so overboard, it doesn't do anything but waste taxpayers' dollars." Cherilus is appealing the decision.

Dumas and Vidale say they intend to protest in Destry's courtroom.

Smith got another chance at freedom.
Smith got another chance at freedom.
Photo courtesy of Herbert Smith

Following the publicity over Destry's harsh sentence and then reduction of it, Herbert Smith was offered a job as an irrigation technician at Cutting Edge Industries in Pompano Beach, mostly installing sprinklers at local businesses. He earns $13 an hour, and his boss, James Jankowski — a felon who turned his life around to open the business — says he's been coming to work every day for the three months since his case made the news. Smith has even started going to church on Sunday, his grandmother tells New Times.

Destry was reelected to his seat in 2010. Greenwald has announced that he will run against Destry this November, when Destry is up for reelection again.

"This is a call to arms," Greenwald says. "Herbert Smith was the straw that broke the camel's back."

The primary election is on August 30, and the general election is in November. In the meantime, Greenwald says that even if he doesn't win, he hopes to make a difference.

"The fact that I am running, if that does anything to change what happens in that courtroom, is a win for me," Green­wald says. "It always sounds cheesy, but I went into law to help people."

Greenwald says attorneys stop him every day to offer support. Matt Glassman is treasurer of Greenwald's campaign. The pair have been friends for more than a decade, since they both worked in the Public Defender's Office.

"I'm ecstatic. Brian is a tireless litigant and fights very, very hard and is very smart when it comes to the law," Glassman says. "The bottom line is that his opponent reduces the integrity of the judiciary for everyone else, but Brian I think can restore it."

Ratonya Dumas was relieved to hear that Destry is being challenged. "This judge needs to be removed from the bench because he doesn't have the best interest for people of color," Dumas says. "This man needs to be exposed for the things that he is doing."

Smith might have escaped a harsh sentence, but for the next 15 years, the tiniest infraction on his probation could land him in prison for the rest of his life.

At least "Judge Destry gave Herb the golden opportunity to do the right thing," Greenwald says. "This time I know he'll do better."

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