In Merciful Sentence, Judge and Prosecution Recognize Defendant’s ‘Huge Service’ in Securing Other Convictions

McCaskill got off with the most merciful sentence so far: no prison. Six months at the local county jail, with credit for more than two months already served, two years of house arrest, with allowance for traveling to and from work, followed by three years on probation. He had faced up to 45 years in prison, based on his initial charges. But he had pleaded (as had all the others). The plea deal included the state’s agreement that he would be sentenced as a juvenile. McCaskill had also cooperated with prosecutors, pointing the finger at Jimaya Baker, the ringleader, and Jimari Baker.

Prosecutors had skillfully, ruthlessly used different members of the conspiracy against each other at different points of the investigation and as the cases lumbered through court over the past three years, securing convictions in every case without having to go to trial.

“Mr. McCaskill was cooperative, to be frank with the court, had he not proffered,” said Assistant State Attorney Melissa Clark, who prosecuted the case, using the legal term that means cooperating with the prosecution by presenting evidence that can’t be used against him, “I would not have been able to prosecute Jimari Baker, the gunman, so it was essential for us to have his cooperation in order to make that happen. And he did. He proffered for us.” She added later: “Because of that cooperation, we were able to go after the gunman, and also ensure that Jimaya Baker was punished for her involvement in a second robbery.”




Jimaya Baker was sentenced to 15 years in prison in January. Jimari got three years in prison followed by five years on probation. Diovion Smith got five years.

Princess Williams, who inadvertently pulled the trigger of the gun she was holding as she was opening the door to the car the victim, Carlos Saint Felix, was driving to get away from the robbers, is the only defendant who has not been sentenced yet, though she has been at the county jail for three and a half years. She will turn 25 in June. She pleaded in December 2019. Her sentencing has been rescheduled several times since, the next one now scheduled for July 15 at 9 a.m. (“I am seeking leniency to be able to go home on an ankle monitor and community control,” she wrote Circuit Judge Terence Perkins last May. “I have a disabled mother who is having spinal surgery and will not be able to walk or care for herself for sometime.” In her letter, Williams tells the judge that in her time at the jail she has been “assaulted more than once sexually and physically.” She was denied release.

She faces three charges, each of which rate up to life in prison: attempted murder, armed robbery and armed burglary. The minimum mandatory prison sentence she faces is 25 years, absent a so-called “downward departure,” which a judge could make, with stated justifications. She pleaded on January 27, 2020. It was an open plea, which means the judge can impose any plea deemed appropriate. The attempted robbery and shooting of St. Felix took place on Oct. 16, 2018, at 50 Whitestar Drive, when she was 21.




Williams was arrested two days later and jailed, in essence ensuring that she would not be involved in her co-conspirators’ subsequent robbery almost exactly a year later at 48 Seven Wonders Trail, where the victims were two teenagers–the robbery McCaskill took part in.

McCaskill had held one of the victims down while Jimaya Baker took cash from him. The two teens were “dealing cannabis out of their house,” Clark described it. “Jimaya Baker was the gunman” in that incident, Clark said.

Now 22, McCaskill has been been working at Sonny’s full-time for two years, he told Circuit Judge Terence Perkins. He’s working on his commercial driver’s license (he took the test at the end of February). He lives with his parents, contributing to the household’s bills.

Scott Westbrook, his attorney, asked him if he’d collaborated with the state about who did what during the robbery. He said he had. He had admitted to his part in the crime, and provided information to investigators indicating that both Bakers were directly involved. He had moved in with the Bakers when he was 19, “for a couple of months,” he said.

“And to the best of your ability, did you give truthful testimony to the state?”

“Yes, sir,” McCaskill said. He said he was “very” remorseful that the crime took place at all. “Also, I feel like I don’t want one situation to define me as a person as to who I am, as who I’m trying to be. I don’t want like one mistake that I made to define me as a person.”

“Do you understand that you are charged with a crime that legally you could be sentenced up to 15 years in prison?” He understood.

Because of McCaskill’s cooperation, Clark agreed to lessen the charges, eliminating the firearm component from the robbery charge and agreeing to a youthful offender status. Clark was not advocating for prison, saying McCaskill “did the state of Florida a huge service” by securing other convictions–a pair of words McCaskill can now wear as a badge at his future job interviews. She insisted that McCaskill maintain full employment and of course have no contact with the other conspirators. She was also concerned about two youthful offender cases when McCaskill was charged with pot possession, suggesting an issue with substance abuse.




“I can’t argue with the state’s position that it looks like that was an issue in this particular case too,” Westbrook said. McCaskill has no room for violating the terms of his sentence (house arrest and probation), as violations would land him in prison. Westbrook disputed none of the prosecution’s demands, with one exception: McCaskill was facing six months in jail. Westbrook said that would cause him to lose his job at Sonny’s and derail his hopes of becoming a commercial truck driver. He also asked the judge to “give my client a chance to show that he could be somebody different,” and not convict him as a felon.

Clark deferred to Perkins on those matters. “There’s some good parts and bad parts that are appropriate in this case,” Perkins said. He agreed to the youthful offender status, because of McCaskill’s cooperation. “But at the end of the day, we’re still left with the fact that this was a planned robbery,” the judge said. “And that’s very troubling to me.” He did not budge on the 180 days in jail. “I think that there’s an element of this that was bad, and it was bad wrong and you knew it was bad wrong when it happened. And that’s why the jail sentence,” Perkins said.

But Perkins withheld adjudication, meaning that McCaskill will not be a convicted felon, in recognition that McCaskill was not today the person who’d committed the robbery three years ago.