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An overdose. A life sentence. Brandon man’s case denotes stark legal realities.

Christopher Ashley Defilippis will be in prison for life after being found guilty at trial of causing a man’s death.
The Sam M. Gibbons United States Courthouse in downtown Tampa.
The Sam M. Gibbons United States Courthouse in downtown Tampa. [ Times ]
Published Sep. 14

TAMPA — The U.S. Constitution guarantees everyone a right to a trial. But the vast majority of those accused of crimes opt to work out a plea deal rather than gamble on a jury.

Christopher Ashley Defilippis was in the minority. Accused in federal court of distributing fentanyl last year to an east Hillsborough man who overdosed and died, he opted for a trial.

It was a decision that may have cost Defilippis, 43, a lifetime.

He was found guilty in June. Last week, a federal judge imposed what prosecutors had ensured would be the only available sentence: life in prison.

Christopher Ashley Defilippis, 43, was sentenced to life in prison after he was found guilty of distributing fentanyl resulting in death.
Christopher Ashley Defilippis, 43, was sentenced to life in prison after he was found guilty of distributing fentanyl resulting in death. [ Pinellas County Sheriff's Office ]

The outcome amounted to what Tampa defense attorney Michael Maddux said was a disproportionate punishment. It underscores what the lawyer described as the broader issue of mandatory sentences and prosecutors pursuing harsher outcomes for defendants who don’t plead guilty.

“The system is flawed when prosecutors act as legislators changing sentencing outcomes because an accused elects to have his Constitutional right to a jury trial,” Maddux said. “This is an improper trial tax.”

The man who died is identified in court records by the initials “J.R.” On the night of April 17, 2020, he drove with his girlfriend, identified by the initials “A.F.,” to a Chase Bank in Valrico. He was there to buy drugs, according to court documents. He got out of his car and later returned. His girlfriend would later say that she did not see Defilippis there, but recognized a red car at the bank as belonging to him.

The pair returned home, where A.F. argued with J.R. about his drug purchase, according to documents. They went to sleep in separate rooms. When A.F. got up about 10:30 that morning, she found her boyfriend dead.

Toxicology tests showed fentanyl, the powerful opioid drug, in J.R.’s blood when he died, according to records.

Investigators pulled surveillance video from the bank, which showed what appeared to be a red Honda Civic, whose driver used an automated teller machine about the same time that J.R. and A.F. drove there. Records also showed Defilippis accessed his bank account at that time.

Hillsborough sheriff’s deputies later sent text messages to Deflippis, using a “ruse” to draw him back to the bank for another drug buy, records state. On him they found fentanyl, cocaine, and “packaging consistent with distribution,” prosecutors said.

Search warrants revealed a series of Facebook messages J.R. and Deflippis exchanged in which the two appear to discuss money and payments.

Deflippis, of Brandon, was indicted in November on charges of distribution of fentanyl resulting in death and possession with intent to distribute fentanyl.

In May, Assistant U.S. Attorney Diego Novaes filed a notice detailing five drug-related felony convictions in Deflippis’ past. The prosecutor said the government would rely on those convictions to seek an enhanced penalty, which the law mandated should be a life sentence.

“This timely notice allowed Defilippis to decide whether to plead guilty or go to trial and to plan his trial strategy with full knowledge of the penalties he faced,” Novaes later wrote in a sentencing memo.

Maddux, the defense attorney, said Defilippis was offered before trial a sentence of less than seven years if he agreed to cooperate. He turned it down.

Prosecutors would not confirm if there had been any plea offers made. William Daniels, a public affairs officer for the U.S. Attorney’s Office in Tampa, provided a statement to the Tampa Bay Times, which said that while they typically refrain from discussing the substance of plea negotiations, the office never agreed to a seven-year prison term, but continuously maintained that Deflippis should “serve a sentence befitting his crimes.”

“The illegal distribution of dangerous drugs has fueled the opioid epidemic that has ravaged countless communities and shattered too many lives,” the statement read. “Our office treats drug distribution cases resulting in death as homicide cases and remains fully committed to working with our state and local partners to combating this crisis and preventing further victims. The outcome in this case is consistent with that approach and strategy.”

Maddux said Deflippis’ has struggled with addiction, having overdosed several times and being saved with Narcan, the drug that blocks the effects of opioids.

“This is the sad cycle of addiction – distributing to support one’s own lethal habit,” Maddux said.

A 2018 report from the National Association of Criminal Defense Lawyers found that 97 percent of federal cases resolve with plea deals, while fewer than 3 percent go to trial. This represented a 50-year period decline in the number of trials, which the report attributed to the higher sentences defendants tend to face if they go to trial and lose.

Advocates say the solution is to do away with mandatory minimum sentences and allow judges more discretion.

“If you assert your right to a trial, you’re going to pay a heavier penalty when it comes to sentencing,” said Kevin Ring, president of Families Against Mandatory Minimums, an organization that advocates for criminal justice reforms. “There is no other Constitutional right that gets punished so heavily for exercising it. It happens all the time.”