The Unthinkable Reality of Florida’s Most Sadistic Predator | True Crime Documentary

Added: 2026-06-01

[00:00:02]Florida Duval County Jacksonville Cherish Periwinkle was 8 years old. She loved drawing animals. She had just learned to ride her bicycle. She was the kind of child who made people smile without trying.

[00:00:18]And the next morning she was supposed to board a flight to California. She never made that flight.

[00:00:24]On the evening of June 21st, 2013, somewhere across Jacksonville, Florida, a convicted predator with nearly four decades of violent criminal history had been free for exactly 3 weeks.

[00:00:37]He was already looking for his next victim. He found her inside a Dollar General Store listening to a mother describe how little money she had.

[00:00:46]By 10:00 that night, Cherish was gone.

[00:00:50]And it would take law enforcement 6 hours to issue an Amber Alert.

[00:00:55]This is what happened. If you're new here, take a moment right now to subscribe and hit the notification bell. And when you're done watching, drop your thoughts in the comments below.

[00:01:06]It means more than you know. We are starting now. Welcome to today's episode, Silent Predator, The Cherish Periwinkle Case.

[00:01:19]Jacksonville, Florida >> [music] >> June 21st, 2013 It was a Friday evening, warm and humid, the way only a Florida summer can be.

[00:01:31]For 8-year-old Cherish Lily Periwinkle, the night carried a particular kind of excitement. [music] The next morning, she was scheduled to board a flight to California to visit her biological father, Billy Periwinkle, a trip that had been [music] a long time coming, tangled up as it was in a bitter, drawn-out custody dispute between [music] Billy and Cherish's mother, Rain. Cherish was the kind of child people remember. [music] Bright, funny, always cracking jokes.

[00:02:00]She loved drawing [music] animals and she had recently learned to ride her bicycle, something she brought up with barely concealed pride at every opportunity. To everyone who knew her, she was vibrant and full of life.

[00:02:13]But on this particular evening, the Perrywinkle family was under real financial strain. [music] Rain, a single mother, was trying to put together something appropriate [music] for Cherish to wear on the trip.

[00:02:25]She loaded her three daughters into the car, 8-year-old Cherish, 6-year-old Destiny, and 5-year-old [music] Nevaeh, and drove to a nearby Dollar General store to look for a dress.

[00:02:37]Inside the [music] store, the stress Rain was carrying became visible. She confided openly to a store employee about her money troubles, expressing genuine anxiety over [music] how she was going to cover even the basics for her daughter's trip.

[00:02:52]She was not speaking [music] quietly.

[00:02:54]Her words carried through the aisles.

[00:02:56]She had no way of knowing that someone was [music] standing nearby listening to every word.

[00:03:03]As the family made their way out of the Dollar General and into the evening air, a man approached them. [music] He was 56 years old with gray hair and an easy, reassuring manner.

[00:03:15]He introduced himself simply as Don.

[00:03:19]Don had a story. His wife, he explained, was waiting over at a nearby Walmart on Lem Turner Road.

[00:03:25]She had a $150 gift card, one they'd never used themselves, and he would be happy to take Rain and her girls over there [music] and let them spend it on whatever they needed.

[00:03:35]Rain hesitated. She was cautious. She studied the man and he met her eyes directly. "You look like you have your hands full," he told her.

[00:03:44]"I have a couple of little ones myself.

[00:03:46]You're safe."

[00:03:48]It was exactly the right thing to say to a mother who was exhausted [music] and struggling. She accepted.

[00:03:54]The family climbed into his vehicle, a white Dodge van fitted with dark, heavy privacy curtains over the rear windows.

[00:04:01]They arrived at the Walmart on Lem Turner Road just after 8:00 in the evening. For the next 2 hours, the group moved through the store.

[00:04:10]On the surface, it looked unremarkable.

[00:04:13]A man accompanying a mother and her children on a shopping trip. But the Walmart's high-definition surveillance cameras were capturing something more specific. The man maintained a deliberate distance from Rain for most of the time they spent in the store.

[00:04:28]He rarely engaged with her directly.

[00:04:31]Instead, he drifted to the edges of the group, watching.

[00:04:34]And his gaze returned again and again to the same place.

[00:04:38]To 8-year-old Cherish.

[00:04:41]At some point during those 2 hours, he pushed a shopping cart. The only item he placed into it was a bundle of rope.

[00:04:49]Rain noticed, but she couldn't have fully processed what it meant.

[00:04:53]She was managing two restless younger children, growing increasingly impatient, and the man's wife had still not appeared with the promised gift card.

[00:05:02]By 10:00 p.m., the children hadn't eaten dinner. They were tired and hungry.

[00:05:08]The shopping trip was beginning to unravel.

[00:05:11]Sensing Rain's frustration, the man made a pivot. He pointed toward the McDonald's located near the front entrance of the store.

[00:05:19]He would get the family some food, he said. [music] He mouthed to Rain that he was taking Cherish up to the counter to place their order.

[00:05:26]Cherish, excited at the idea of a cheeseburger, followed him willingly.

[00:05:31]Rain stayed behind with Destiny [music] and Nivea. Minutes passed, then more minutes.

[00:05:38]Rain began to feel uneasy. She moved toward the front of the store, scanning the area near McDonald's. There was no No of Cherish, no sign of the man. Then the store's PA system crackled on.

[00:05:51]An announcement [music] informed customers that the store was closing for the night.

[00:05:55]In that moment, a detail crystallized with awful clarity. [music] The McDonald's inside that Walmart had already been closed for hours. Rain began to panic. Her mobile phone was malfunctioning. She could not get a call out.

[00:06:11]She ran through the store's closing time crowds shouting for help, telling anyone who would listen that her daughter had been taken.

[00:06:19]In the confusion of customers and employees clearing out, it took nearly 40 minutes before a store employee directed her to a landline. She dialed 911.

[00:06:29]On that call, Rain told dispatchers exactly what she had seen and felt throughout the evening. She described the man. She described the van. And she said something that would later stand as one of the most important details in the case.

[00:06:46]911 Hi, at Walmart.

[00:06:49]I was just trying to say my daughter's been taken.

[00:06:52]What do you mean?

[00:06:54]Taken by a stranger.

[00:06:57]I can't find her.

[00:06:59]I met a man today at Dollar General. He saw that I was struggling to buy them some clothes.

[00:07:05]He drove us here to buy us some clothes and the only reason I went with him because he said his wife was going to be here.

[00:07:12]Okay, and she was last seen with this man? Yes, she went to he said he was going to McDonald's and he he doesn't been there.

[00:07:21]Because the store [clears throat] is closed right now.

[00:07:25]I had a bad feeling about him. Okay, how long have you been looking for her? When was the last time you saw your daughter?

[00:07:30]How long ago?

[00:07:32]About half an hour ago.

[00:07:35]Okay, ma'am. What's your daughter's name? Her name's Cherish.

[00:07:39]And her her last name? Perrywinkle with a P. I had a strange feeling about him when I first met him. He took her to the He took her to the the to the dressing room twice.

[00:07:50]And I was hoping that she would be okay.

[00:07:52]And I was looking at the shoes.

[00:07:55]And I didn't want him to think that I was overly protective. I had a bad feeling. I thought, "Well, I feel like pinching myself because this is too good to be true."

[00:08:06]He was giving my 8-year-old too much attention.

[00:08:10]He wanted her to buy these really tall shoes that were women's shoes, and I told him no.

[00:08:17]I don't want him to kill her.

[00:08:21]I should have told him no.

[00:08:24]The first police officers arrived at the Walmart within 10 minutes of that call.

[00:08:29]What followed in the critical early hours of the investigation was a failure with devastating consequences.

[00:08:36]Despite Rain's detailed, [music] explicit account of a stranger who had deliberately separated her daughter from the group, law enforcement initially classified Cherish as a standard missing person case rather than an abduction.

[00:08:51]This single classification decision had a cascading effect on everything that came next.

[00:08:58]An Amber Alert, the National Emergency Broadcast System specifically designed for child abductions, was not [music] issued until 4:00 a.m.

[00:09:07]By that point, Cherish had already been out of the store [music] for more than 6 hours.

[00:09:12]When investigators finally pulled and reviewed the Walmart surveillance footage, the reality of what had happened was not ambiguous.

[00:09:20]The footage clearly showed the man leading Cherish out of the store [music] through a side exit, guiding her toward the white Dodge van, and driving away past the security checkpoint into the dark.

[00:09:31]By 3:30 a.m., investigators had run the van's [music] description and identified its registered owner. His name was Donald James Smith.

[00:09:42]Donald Smith was not a stranger [music] to the criminal justice system. He was a tier three registered sex offender, the highest possible risk classification, with a violent criminal history stretching back nearly four decades.

[00:09:57]Among his prior convictions was a 1992 case in which he had attempted to kidnap two teenage girls using a van.

[00:10:05]He had been in and out of custody for much of his adult life. And critically, shockingly, [music] he had been released from prison just 3 weeks before the night he walked into that Dollar General and listened to Raine Perrywinkle >> [music] >> describe her troubles to a store clerk.

[00:10:23]3 weeks. The Amber Alert, once issued, went out to televisions [music] and radio stations and phones across the Jacksonville area.

[00:10:31]And it worked quickly.

[00:10:33]At 7:20 in the morning, a citizen watching the local news recognized the white Dodge van.

[00:10:39]They had seen it parked in a heavily wooded area behind a church not far from the Walmart. They called authorities immediately. Hi, we've calling about a suspicious van over here, a white van.

[00:10:51]>> [music] >> And how long ago did you see it? About 7:20 or 7:20. It was like that. We didn't say nothing. We didn't know anything until just now. It's not there anymore, but we don't know if he dumped anything cuz we heard a girl just got a gun at the Walmart. All right, and you said it's now gone? Yes. Yes, ma'am. But you think he may have, just in case, he might have dumped something? Right, we don't know, but just in case, it looked suspicious cuz it was all the way to the back. By 9:00 a.m., state troopers and Jacksonville police spotted the van moving on Interstate 95. They moved to surround it, boxed it in, drew their weapons, and ordered the driver out of the vehicle.

[00:11:32]>> [music] >> Donald Smith stepped out. He was soaking wet from the waist down.

[00:11:37]K9 officer Charlie Wilkie approached Smith and immediately noticed the state of his clothing. He later testified to what he said in that moment. Oh my god, she's in the water.

[00:11:49]Smith said nothing.

[00:11:50]>> [music] >> But the officers reported that a look crossed his face, a cold involuntary flicker of realization that confirmed what they already feared.

[00:12:00]K9 units were deployed immediately. They tracked a path from the wooded area behind the church down through brush and undergrowth to the bank of a nearby tidal creek. There, partially concealed beneath a fallen tree trunk, investigators discovered the body of Cherish Perrywinkle.

[00:12:17]The bright flowery dress she had been wearing was found nearby.

[00:12:22]The subsequent autopsy conducted by medical examiner Dr. Valerie Rao documented what Cherish had endured in the hours after she left that Walmart.

[00:12:32]She had suffered severe blunt force trauma to her head.

[00:12:35]She had been violently sexually assaulted. She had been gagged and she had been strangled with such force that she experienced hemorrhaging in her eyes.

[00:12:44]>> [music] >> She was 8 years old.

[00:12:47]Donald Smith was taken into custody and transported to the Duval County Jail.

[00:12:53]In the interrogation room, he sat in complete silence.

[00:12:57]He refused to speak to detectives. He answered no questions. He offered nothing.

[00:13:02]Have a seat. We'll be with you in a little bit.

[00:13:05]What's your name?

[00:13:06]Donald Smith.

[00:13:08]Donald Smith? Yes. If you do answer questions, you have the right to stop answering questions at any time. Consult a lawyer. You understand that? This is an investigation of the abduction and murder of a Cherish Perrywinkle. Yeah.

[00:13:20]8-year-old female.

[00:13:21]Uh We'd like to ask you questions about it. Do you want to talk to us? No. Okay.

[00:13:26]But he had no idea how much he was about to give away on his own.

[00:13:30]The Duval County Jail had video and audio recording equipment installed in its visitation areas.

[00:13:37]Between late June and July of 2013, Smith received multiple visits from his mother, Patricia Moore.

[00:13:45]Those conversations were captured in their entirety. What the recordings contained would become some of the most damaging evidence in the case.

[00:13:54]I'm panicking.

[00:13:56]I'm panicking.

[00:13:57]You know, sex trafficking. Little girl on the on the corner of my block with security right there. Her mother is inside.

[00:14:06]My mind is weak.

[00:14:10]Weak.

[00:14:11]I'm shaking because now this is kidnapping.

[00:14:16]You know, girl. [ __ ] I'm afraid of this girl. I'm panicking. [clears throat] And I'll be okay. Okay. Okay. I'm going to start my day. I'm going to start my day.

[00:14:25]I look at the door. And I'm thinking, "Holy [ __ ] I don't know what to do." My mind My mind it just went I'm feeding children sexual objects.

[00:14:38]I'm feeding sexual objects. Sexual objects to children. All of them.

[00:14:44]Yes, that. I snap.

[00:14:47]I'm going to do this.

[00:14:50]You just love me. All I knew was you got to go.

[00:14:54]You got to go.

[00:14:56]I don't care how. You got to go.

[00:15:01]It happened.

[00:15:02]It couldn't have happened the way they said?

[00:15:04]>> Yes, they could have.

[00:15:06]They could have.

[00:15:10]I was so so hard.

[00:15:12]I was extremely hard.

[00:15:15]She wanted to go.

[00:15:17]I don't care how. She had to go.

[00:15:20]She had to go.

[00:15:21]That's my why I say like that.

[00:15:24]They'll kill me.

[00:15:26]You're all going to die.

[00:15:29]I want to break you.

[00:15:34]Why don't you just kill me? Never be able to work through all this. Never.

[00:15:38]I'll never be okay. So, rather than spend the rest of my life being humiliated by myself, telling all this crap in my head, I might as well just die with it.

[00:15:54]Easier to just die with it cuz I'll probably never get through it anyway.

[00:15:57]That's what my brain's telling me. I need a very simple book.

[00:16:05]In another recording from June 28th, Smith gave his mother specific instructions. He told her to purchase a copy of the DSM-IV, the diagnostic and statistical manual of mental disorders, the standard reference guide used by psychiatric professionals.

[00:16:22]He was not curious about it academically. He told her plainly, "Mental illness is my whole defense, basically.

[00:16:30]And it's got to be good." He was, while sitting in a jail cell awaiting charges for the murder of a child, actively constructing a legal strategy and coaching his own mother on how to support it.

[00:16:42]In other recorded conversations, Smith was heard boasting to fellow inmates that his case was way bigger than Casey Anthony, a reference to the 2008 Florida child murder case that had dominated national headlines for years.

[00:16:57]He appeared to take satisfaction in the scale of attention his case was receiving.

[00:17:03]The fallout from Cherish's murder reached into every corner of what remained of her family.

[00:17:09]Rain Periwinkle became a target of intense public [music] criticism. Much of it was directed at her decision to trust a stranger and to allow her daughter to walk away with him inside the store.

[00:17:21]What was often lost in that criticism was the clinical precision with which Donald Smith had selected his target. He had spent time in public [music] spaces listening for vulnerability.

[00:17:34]He had crafted an offer calibrated [music] specifically to what Rain needed. He had built trust across nearly 2 hours of ordinary seeming behavior. He had been convicted of attempting almost this exact crime before.

[00:17:48]Regardless, the Florida Department of Children and Families opened an investigation. Less than a month after the murder, the state removed Destiny and Neveah from Rain's care citing a failure to protect. Rain entered a state case plan, but ultimately did not fulfill its requirements. [music] In 2017, after a prolonged legal battle, her parental rights to both surviving daughters were permanently terminated.

[00:18:16]The two girls were adopted by their biological aunt and relocated to Australia where they have built lives at a significant distance from everything [music] that happened in Jacksonville.

[00:18:28]The question of how Donald Smith came to be walking free on the night of June 21st, 2013, 3 weeks after his most recent prison release, prompted serious scrutiny of Florida's sex offender monitoring system.

[00:18:44]A Tier 3 classification is reserved for offenders [music] considered the highest risk of reoffending. The system that allowed Smith to [music] exit prison with minimal structured supervision and reenter the community was examined in the aftermath of the case. The 6-hour Amber Alert delay was similarly scrutinized. The failure to immediately classify Cherish's disappearance as an abduction, despite Rain's explicit account of a stranger isolating her child prompted calls for reform in how law enforcement triages [music] missing children cases involving potential predatory contact.

[00:19:22]Donald Smith's trial was [music] delayed for nearly 5 years, in part due to ongoing legal challenges and debates surrounding Florida's death penalty [music] statutes.

[00:19:34]It finally began in February 2018.

[00:19:37]The state's case was built on multiple reinforcing layers of evidence. Walmart surveillance footage showing Smith leading Cherish out of the store, DNA evidence recovered from Cherish's body, forensic data from the crime scene, and the jailhouse recordings in which Smith had effectively confessed in his own words and outlined his own defense strategy.

[00:20:00]During the trial, Dr. Valerie Rao took the stand to present the findings of her autopsy.

[00:20:07]Her testimony about the nature and extent of Cherish's injuries was so graphic and so [music] emotionally difficult that at one point the presiding judge called a temporary recess. Um on the left side of her scalp right there.

[00:20:22]>> Right.

[00:20:24]And [snorts] what how is that caused, Dr. Rao?

[00:20:27]Um blunt trauma.

[00:20:29]I'm going to show you two more photographs of the dissection taken of Cherish Perrywinkle's throat.

[00:20:36]Will you first tell the jury what you saw when you um dissected her throat?

[00:20:42]Yes, so what we do is it's uh I'm sorry, I have to take a break.

[00:20:48]Can I just have like 5 minutes?

[00:20:52]Do you want a 5-minute break?

[00:20:56]I think we'll all take a break for 10 minutes. Thank you.

[00:21:01]Dr. Rao, a seasoned medical examiner, was visibly shaken.

[00:21:06]So was the jury. So was much of the courtroom.

[00:21:09]The defense mounted no counter-argument.

[00:21:12]They called no witnesses.

[00:21:14]When the time came for closing statements, Smith's attorneys chose to present none.

[00:21:19]On February 14th, 2018, the jury retired to deliberate.

[00:21:25]19 minutes later, they returned.

[00:21:29]May be seated.

[00:21:34]Thank you, ladies and gentlemen. It's my understanding the jury has reached a verdict. Is that correct?

[00:21:39]In the Circuit Court of the Fourth Judicial Circuit, in and for Duval County, Florida, case number 16-2013, State of Florida versus Donald James Smith, verdict count one, we the jury find the defendant guilty of first-degree murder as charged in the indictment.

[00:21:54]We further find the killing was premeditated. We further find the killing was done during the commission or attempted commission of a felony, to wit, kidnapping and sexual battery.

[00:22:05]Verdict count two, we the jury find the defendant guilty of kidnapping as charged in the indictment. Verdict count three, we the jury find the defendant guilty of sexual battery upon a person less than 12 years of age as charged in the indictment. So say we all done at Jacksonville, Duval County, Florida.

[00:22:20]Signed by the foreperson, February 14th, 2018.

[00:22:25]Okay, thank you, ma'am.

[00:22:26]Donald James Smith was found guilty on all three counts.

[00:22:30]First-degree premeditated [music] murder, kidnapping, and sexual battery of a child under 12.

[00:22:37]At sentencing, the presiding judge addressed Smith directly.

[00:22:42]Reviewing the aggravating factors that we unanimously found to be proven beyond a reasonable doubt, we the jury unanimously find that the defendant, Donald James Smith, should be sentenced to death.

[00:22:55]His legal team pursued multiple avenues of appeal in the years that followed.

[00:23:00]In 2021, the Florida Supreme Court reviewed the case and unanimously upheld the conviction.

[00:23:08]In May 2024, a judge denied Smith's final significant motion for a new trial, which had argued that his original [music] defense counsel performed ineffectively during jury selection.

[00:23:21]As of today, Donald James Smith remains on Florida's death row awaiting execution.

[00:23:28]Cherish Periwinkle would have been 20 years old this year.

[00:23:31]She never got to take that flight to California. She never got to grow up.

[00:23:36]What her case left behind, beyond the grief of those [music] who loved her, is a record of every point at which the systems that should have prevented her death failed to function as intended.

[00:23:46][music] A predator with a decades-long history of targeting children was released with inadequate supervision.

[00:23:55]A mother's explicit description of an abduction in progress was categorized incorrectly. An alert that might have found Cherish alive was delayed by six critical hours.

[00:24:06]Each of those failures had a human cause and each of them has been examined in the years [music] since.

[00:24:13]Some changes have been made. Whether they are sufficient is a question that cases like Cherish's continue to demand we [music] keep asking.