Episode 065: Ali Gilmore – Bite-Sized Crime

When a pregnant woman disappears from her Tallahassee home in the dead of night, investigators uncover secrets and lies that leave everyone wondering: Where is Ali Gilmore?

Episode Media

Dwight Aldridge *(Florida Department of Corrections)*

Episode Sources

Episode Transcript

Welcome back to Bite-Sized Crime. This week I’m bringing you a missing persons case from Florida, a story of a mother-to-be and a family that has waited so long for answers. This episode discusses sensitive topics, so listener discretion is advised.

Ali I-isha Grimsley grew up in the city of Riviera Beach on the east coast of Florida, about an hour north of Miami. Her mother, Laurvetta, was in a tough spot at the time of Ali’s birth in 1976, so she sent baby Ali to live with family members until she could get on her feet. At the age of 11, Ali reunited with Laurvetta, and they moved into a small one-story house in Palm Beach County.

Laurvetta worked multiple jobs to provide for Ali and her siblings. In an interview with the Tallahassee Democrat, Laurvetta said, “I wanted the best for my children… I wanted them all to go to school.”

Ali appreciated her mother’s commitment to her education, and she understood how important it was. As a teenager, Ali would get up at 5am to wait at the bus stop, where she would then ride 45 minutes to Jupiter High School, a nationally ranked magnet school in Palm Beach County. Her stepfather Carl told the Tallahassee Democrat that there had been some issues with gang members assaulting girls in the neighborhood, but when he offered to walk Ali to the bus stop each day, “She said no one is going to stop her from going to school… She was going to walk on her own.”

At school, Ali worked hard to get good grades, and she was a prominent member of the school’s track team. After school, she worked part-time at a local Publix grocery store, a job she really enjoyed. That job enabled her to get a scholarship to Florida A&M University in Tallahassee, and in 1993, 17-year-old Ali headed off to college to start the next chapter of her life.

Ali excelled at FAMU, where she majored in health information management. She also enjoyed the city of Tallahassee, which had a low crime rate and a slower pace than Palm Beach County. After graduation, Ali decided to stay, and she began working for the Florida Department of Health in the office of Evaluation and Planning Data Analysis. Of course, she also kept her job at Publix, working in the bakery on the weekends. Ali was thriving as a newly-launched professional, and her family was so proud of her.

About a year later, Ali met James Gilmore. She was at the Governor’s Square Mall looking for a frame for her college diploma, and James was selling frames at a mall kiosk. They struck up a conversation and eventually, James asked for Ali’s number. He later said, “She just seemed real fun to be around. We just hit it off.”

After that, James and Ali were inseparable. A divorced father of three, James loved how Ali brought out the best in him. She encouraged him to go back to school and get his degree at Tallahassee Community College. James said, “She’s been there supporting me the whole way.” Eight months into their relationship, James brought Ali back to the spot where they met at Governor’s Square Mall and asked her to marry him. She said yes, and the couple married in October of 2000.

At first, things were good. James and Ali bought a little blue house in the Wilson Green subdivision, and Ali set about decorating and planting flowers. They talked about having kids and planning for the future. In the summer of 2005, Ali found out she was pregnant, and she was so excited. But sadly, she miscarried shortly after. This was devastating to both Ali and James, and the emotional impact put a strain on their relationship. They struggled to communicate, and they began to withdraw from each other.

Adding to this stress was their financial situation. Ali was working full-time for the Department of Health and working evenings and weekends at Publix. James was going to school part-time and working as a stockman at Albertsons supermarket. They were barely making ends meet, and they hardly saw each other due to their busy schedules.

Things came to a boiling point in October of 2005, and the couple decided they needed space. James moved out and went to stay with his brother, but he and Ali kept in contact during their time apart. Not long after their separation, Ali discovered that she was pregnant again, and she was over the moon. She and James decided to start going to counseling together, hoping that they could eventually reconcile.

By the time 2006 rolled around, Ali was once again feeling hopeful. She had just turned 30, her pregnancy was healthy so far, and she was planning a baby shower with her friends. She and James were still living apart, but things were looking up. Counseling had been going well, and they were both excited about the baby, decorating the nursery and picking out potential baby names. They had an appointment coming up in mid-February to find out if the baby was a girl or a boy.

Of course, life wasn’t without its stressors. In late January, Ali got the news that her property taxes were increasing significantly, and she was worried about being able to pay the bill. Even with James’ help, it was going to put a big strain on their finances. On Thursday, February 2nd, the issue was still heavy on her mind. She went into work at the Department of Health as usual, driving through a torrential downpour to get there. Her co-workers noted that she was anxious that day, and she even spoke with her supervisor about her taxes, hoping for some advice. After work, Ali left for her evening shift at Publix, once again driving through a thunderstorm and fighting against traffic, none of which helped her anxiety. Later that evening, around 8:45, Ali called James while she was on her break to remind him about their counseling session at 9 the next morning. James said he would meet her there.

But neither of them showed up for the appointment.

Around 11am on Friday, James woke up and realized that he had overslept and missed the counseling session. Figuring that Ali had already gone to work by that time, James called her office and left a message, apologizing for missing the appointment. But Ali wasn’t at work. Her co-workers knew she’d had an appointment that morning, so they assumed that she would be in later, and her supervisor was out sick that day, so she didn’t know that Ali wasn’t there. Everyone just assumed that Ali was somewhere else.

But by Saturday, James was getting worried. Ali hadn’t responded to his messages, which wasn’t like her, even if she was upset. He drove over to the house and saw that her car was in the driveway, but when he knocked on the door, she didn’t answer. James figured that she must be really angry with him and didn’t want to talk. Wanting to respect her space, James left.

Unfortunately, it would be another two days before anyone realized that Ali wasn’t just mad – she was missing. When she didn’t show up for work on Monday, and her supervisor realized she hadn’t been there Friday either, she tried calling Ali’s home phone over and over again to no avail. She finally drove over to Ali’s house with another co-worker, and the two banged on the doors and windows, hoping to get a response. They noticed that one of the bedroom lights was on, as well as the floodlight in the front of the house. If Ali was home and hurt, she may not have been able to get the door. Her co-workers decided to call the police.

When officers from the Tallahassee Police Department arrived, they agreed with Ali’s co-workers – it was likely that Ali was inside and in need of assistance. They were able to get into the house, but once they did, they quickly realized that Ali wasn’t there. The house was quiet and seemingly undisturbed. In Ali’s bedroom, the light was on and the bedsheets were pulled back, a book on prenatal care next to the pillow. On the end of the bed, Ali’s Publix uniform was laid out, indicating that she had made it home after her shift on Thursday night. Officers observed that there were no obvious signs of a struggle – it appeared as though Ali had been lying in bed reading, then had gotten up for some reason.

When officers searched Ali’s vehicle, they found that her purse was inside the car with her work keys, but her house keys and car keys were missing. Apparently, leaving her purse in the car wasn’t unusual for Ali – her friends said she often did this, but always locked the car behind her. Investigators were left wondering – why would Ali leave the house so late at night after already getting settled into bed? And where would she go without a car?

The next day, a forensic unit searched the house, attempting to find evidence that may have been missed on the first search. They took Ali’s computer back to the lab for analysis, just in case there were any clues in her emails or personal files. Detectives also began canvassing the neighborhood, knocking on doors and asking for any information about Ali. They interviewed Ali’s friends, co-workers, and family members. All of them said the same thing: Ali wasn’t the type to just walk away without telling anyone.

The search for Ali spread across town, starting in her small subdivision and extending into nearby construction sites and wooded areas. Lieutenant Edward Smith, head of the criminal investigations unit, told reporters that although they couldn’t say whether foul play was involved in Ali’s disappearance, “we’re ruling it as suspicious”.

Naturally, some of that suspicion fell on Ali’s estranged husband, James. He was questioned by police multiple times, but they always stated that he was cooperative and willing to help with the investigation. He voluntarily submitted to a polygraph and passed. James spoke with the Tallahassee Democrat early on, saying, “I want everybody to know and understand how much I love and miss Ali… Anybody who’s known me for all of a couple of weeks would know that I am not the kind of person that would render harm to any living soul whatsoever.”

On February 10th, a week after Ali disappeared, nearly 200 people gathered for a candlelight vigil, sharing encouraging messages with Ali’s family and praying for her safe return. But the weeks continued to pass, and there was no sign of Ali. Even investigators were getting frustrated with the lack of movement in the case. Officer David McCranie told reporters, “The way we do an investigation like this is we exhaust every avenue possible and interview every person we can find… We’ve got nothing. We’re waiting for that next bit of information.”

Ali’s friends and co-workers organized search parties and handed out fliers around Tallahassee, hoping to get the word out. At the end of February, the Tallahassee Police Department announced that they were offering a $10,000 reward for any information leading to Ali’s whereabouts. Publix Supermarkets matched that donation, and Crime Stoppers added another $1,000 to the fund. But even with the large reward, very few leads came in, and none of them panned out.

Investigators decided to take Ali’s story to the media. Her case was featured on national shows like Nancy Grace and Anderson Cooper, with members of the Tallahassee Police Department answering questions about the case and asking the public for their help. They hoped that the story of a pregnant woman disappearing without a trace would capture the public’s attention and bring in new leads.

In March, a local advertising agency donated a large billboard on a main road just a mile outside of Ali’s neighborhood. Ali’s smile shone down on passersby, the tip line phone number prominently displayed. By this time, the reward had grown to $30,000, and everyone was hoping for new information.

The search for Ali continued. In April, The KlaasKIDS Foundation partnered with a local K-9 search and rescue group to canvas the Apalachicola National Forest, which spans over 600,000 acres in the Florida panhandle. Hundreds of volunteers joined the search, and news outlets reported that teams handed over 15 possible clues to authorities at the end of the first day. But if anything ever came of those clues, investigators have never said.

Unfortunately, none of these searches brought Ali home, and as time passed, there was less attention on her case.

In February of 2007, a year after Ali disappeared, investigators revealed some new information. On the night of her disappearance, Ali had gotten a phone call at 12:47am – but authorities wouldn’t say who had called. They also said that they had recently gotten lab results back on certain pieces of evidence, and they were sharing that information with the state attorney’s office. In yet another bombshell, investigators announced that although they originally had four suspects in the case, they were now narrowing their focus.

For many who were following Ali’s case, this was brand new information. Who were the four suspects, and what did it mean that the investigation had narrowed? Did the police know what happened to Ali and who had been involved?

It was obvious that Ali’s husband James was one of the four suspects, but he maintained his innocence and police continued to assert that James had been cooperative from the beginning. If they thought he had anything to do with Ali’s disappearance, they didn’t have enough evidence to prove it, and they never filed any charges against him.

In July of 2007, Ali’s case was assigned to the Tallahassee Police Department’s Major Case Assessment Team – the unit that handles cold cases. Investigators said that all their leads had been exhausted, and it was time for the case to be looked at with new eyes. A rotating team of detectives would look at Ali’s case on a regular basis, searching for new clues and answering old questions.

It would be another 14 years before any of those answers came to light.

On October 11, 2021, the Tallahassee Police Department announced that they had a suspect in the disappearance of Ali Gilmore – 40-year-old Dwight Aldridge. They also revealed that he was the one who called Ali the night she disappeared.

Ali met Dwight in October of 2005, not long after she and James had separated. According to Ali’s family, she had gone to homecoming at FAMU and had run into Dwight, who was tall and handsome and swept her off her feet. Ali’s sister Tracy believes that Ali fell for Dwight right away, and there were even questions about her baby’s paternity. In December of 2005, Ali sent Tracy an email, part of which read, “Dwight and I still talk about 2 or 3 times a day. We see each other three times a week. He’s said I changed since I am pregnant. My past miscarriage haunts me every few days, then on top of all of that the paternity issues.” Apparently, Dwight even went to several ultrasound appointments with Ali, which she noted in her day planner.

According to James, Ali told him about her relationship with Dwight during one of their counseling sessions, but they were both still determined to make their marriage work. He told WCTV, “We were going to work it out either way, in my brain that’s where I was… I did not, not want to be with her.” Ali’s family confirmed this – Ali told them repeatedly that she loved James and wanted to work things out with him.

In the early morning hours of February 3, 2006, Dwight called Ali at home. Sometime after that, she vanished. Authorities say they asked Dwight about this call early on in the investigation, but he claimed that he was nowhere near her house. However, cell phone records showed that Dwight’s phone pinged off a tower right near Ali’s neighborhood at the time of the call in question.

This wasn’t the only lie Dwight told about Ali. In 2009, he made a brief statement to the Tallahassee Democrat, claiming that he and Ali were just friends and that he didn’t remember anything about the last time he spoke with her, saying, “It’s been so long.”

In addition to these statements, Dwight’s past may prove troublesome for him if he is ever charged in this case. In 1998, the day after his 17th birthday, Dwight was arrested for armed robbery and sentenced to five years in prison. He was released in 2003, just two years before he met Ali. It’s unclear if she knew about his time in prison; he may never have mentioned it to her, especially since they were only together for a few months.

Obviously, none of this is enough to prove Dwight’s guilt, and I do believe in “innocent until proven guilty”, but investigators waited 15 years to announce that Dwight Aldridge is their main suspect, which leads me to believe that they have much more information than they are releasing at this time.

In the years since Ali’s disappearance, Dwight graduated from nursing school and has been working in health administration in Tallahassee. He has not spoken publicly about Ali since that one interview in 2009. It appears that he has moved on with his life. He has not been officially charged in connection with Ali’s disappearance.

James Gilmore is also still living in Tallahassee. According to public posts on his Facebook account, James welcomed his first grandchild in 2019, and he will occasionally post pictures of himself and Ali. He spoke with WCTV in 2021, saying, “The thing that I think about more, is what could have been. What could have been and us getting back together and raising our- hopefully, it was a daughter.”

Ali Gilmore is still missing, and her family deserves answers. At the time of her disappearance, Ali was 30 years old and four months pregnant. She is 5’6″ with brown hair and brown eyes, and a tattoo of her first name on the right side of her chest. She may have been wearing a platinum and diamond wedding ring when she left her home in Tallahassee’s Wilson Green neighborhood on February 3, 2006. If you have any information about Ali’s disappearance, or about Dwight Aldridge, please contact the Tallahassee Police Department at 850-891-4200, or submit an anonymous tip to Crimestoppers at 850-574-TIPS.