The Disappearance of Jennifer Kesse

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*This article was used as the basis for the 56th episode of John Lordan’s Seriously Mysterious podcast.*


Jennifer Joyce Kesse was born on May 20, 1981 to parents Drew and Joyce Kesse. She was the oldest of two children, and is said to have been best friends with her little brother, Logan.

The pair grew up in Tampa, Florida, and Jennifer is described as having been an adventurous dynamo with a thirst for knowledge. She had the ability to light up a room, and was extremely loyal to her friends. Jennifer was also very cautious, a trait her parents instilled in her and her brother from a young age. This was due to the fact they’d been held up at gunpoint years before in New Jersey.

Jennifer graduated from Vivian Gaither High School in Tampa before attending the University of Central Florida, where she was a member of the Alpha Delta Pi sorority. She graduated with honours in 2003 with a degree in finance. She received numerous job offers and took a job at Central Florida Investments Timeshare Company in Ococee, Florida. A financial analyst, she was promoted twice within her first year.

Jennifer had a good relationship with her boyfriend, Rob Allen. The pair met at a bar in January 2005 while Rob was in Orlando for a trade show. Despite him living in Fort Lauderdale, the pair entered into a relationship and spent virtually every weekend together.

With her success at work, Jennifer was able to purchase a condo at the Mosaic at Millenia condominium complex, in the vicinity of the 3700 block of Conroy Road. At the time, the complex was undergoing a change from apartments to condos and was filled with construction workers. They made Jennifer uneasy, as they would catcall, whistle and verbally harass her.


Jennifer and Rob returned from a vacation to Saint Croix in the US Virgin Islands on the evening of January 22, 2006. Not wanting to make the hours-drive back to her condo, Jennifer opted to stay the night at Rob’s residence.

She drove straight to work from Rob’s the next morning. The last time she was seen was at 6:00pm that evening, as she was leaving work. On the drive back to her condo, she spoke to her father and brother, and that evening made calls to her mother and best friend.

The last person to speak with Jennifer was Rob. They spoke on the phone around 10:00pm.


It’s believed Jennifer left for work between 7:30am and 8:00am on the morning of January 24, 2006. However, she never arrived, nor made her usual phone calls to her boyfriend.

Rob tried calling Jennifer’s cellphone while on his way to work between 8:00am and 9:00am, but each went to voicemail. He assumed she was in a meeting and didn’t worry too much, but his subsequent calls that morning also went directly to voicemail.

Alarmed that she hadn’t shown up for work, Jennifer’s employer contacted her parents around 11:00am. Drew and Joyce’s attempts to contact their daughter had the same result as Rob, and calls to Rob and Logan showed they had no idea of her whereabouts. They contacted hospitals and jails, and called Jennifer’s building manager to check on her condo. He reported that everything appeared normal and that her car was not in its parking spot.

Jennifer’s parents and her brother made the two-hour drive from Bradenton, Florida to Jennifer’s condo, arriving between 3:00pm and 3:15pm. While her suitcase had been left unpacked, they found nothing unusual. There were signs she’d gotten ready for work that morning, as the shower and towels were still wet, clothes were laid out on the bed, and hair and makeup were products strewn across the bathroom counter. The only items missing were her purse, iPod, briefcase, keys, cellphone and her black four-door 2004 Chevy Malibu.

Logan spoke to some of the construction workers on-site, but found them uncooperative. Concerned, Jennifer’s parents called the police, who shrugged off her disappearance, saying she’d likely had a fight with her boyfriend and would return.


Despite the Orlando Police Department’s disinterest in launching an investigation, her family knew something was wrong. They contacted her friends to help distribute flyers along the route she took to work. This effort caught the attention of local media, who broadcast a story about Jennifer.

Her family soon learnt disconcerting information about Jennifer’s apartment complex, beyond what their daughter had told them. Over half of the units were unoccupied, and the security system had yet to be installed. As well, the front gates were left open to allow the construction crews to enter and leave as needed.

At 9:00pm on January 24, Jennifer was officially entered into the police department’s system as a missing person, and a BOLO was issued for her and her vehicle. It wasn’t long after that investigators organized search parties on foot and horseback, as well as by ATV, car, helicopter and boat.

Police worked off a host of theories in those initial days. They initially thought she’d been abducted the night before, but this theory was contradictory to evidence found in her condo. They then believed she’d been abducted walking to her car, but later changed their theory to say she’d likely been abducted on her way to work.

Investigators spoke to a couple in the complex, who said they’d seen Jennifer’s car swerving erratically out of the parking lot around 7:40am, in what police believe points to a struggle for the steering wheel. Unfortunately, they couldn’t tell what way the car went once it passed through the front gate.

Attention was immediately placed on Jennifer’s friends and family, who were questioned. Her parents and brother were eliminated, as was Rob after providing DNA and passing numerous polygraph examinations. Jennifer’s ex-boyfriend was interviewed after it was learnt he’d been at the bar across the street from her condo complex the night before she went missing, but it was eventually concluded he had nothing to do with her disappearance.

Many of the construction workers turned out to be illegal immigrants and thus hastily disappeared upon the police launching an investigation. As such, investigators were unable to question the majority of them. Of those they spoke with, they found the language barrier to be a hinderance.

It was learnt a married manager at Jennifer’s workplace had romantically pursued her, despite her refusing his advances. According to Jennifer’s co-workers, he was very open about his attraction to her, and on the day following her disappearance had said she’d likely been eaten by alligators. He’d also been late for work on the morning of January 24. When asked about this, he said he’d been taken to jail after becoming irate at a police officer for giving him a speeding ticket. After multiple interviews, he was ruled out as a suspect.

Due to the delay in the start of the police investigation, Jennifer’s condo wasn’t secured, nor examined. Her computer was taken for forensic examination, but it’s not known if anything of value was uncovered.

The first break in the case came two days after Jennifer’s disappearance, on January 26, 2006. At 8:10am, after seeing an image of her car on the news, a concerned citizen called to say the vehicle had been parked outside the Huntington on the Green apartment complex at Americana and Texas Avenues for several days. The complex was less than a mile from Jennifer’s condo, and is known for its drug activity. This led police to theorize she’d gone to the area to purchase drugs and had become too intoxicated to walk back home, but this theory was discarded after learning about her lifestyle.

An analysis of the car showed no signs of a struggle. The amount of gas in the tank indicated it hadn’t been driven outside of Jennifer’s normal routine, and a valuable DVD player was still on the backseat. The only indication that something was wrong was a large boot print near the gas pedal and the fact the driver’s seat had been adjusted. The car was photographed and taken for forensic examination. It yielded little in the way of evidence, providing only a latent print that was later determined to belong to Jennifer and a small DNA fibre that proved inconclusive. It was deduced the vehicle had been wiped down by whoever parked it at Huntington on the Green.

Police canvassed the area and asked residents if they’d seen anything unusual. They brought in bloodhounds to track her scent, and they led investigators back to Jennifer’s apartment. No evidence was located along the route back to Mosaic at Millenia.

Investigators thought they’d gotten a break when they learnt there were security cameras around Huntington on the Green. They obtained footage from two cameras, the first of which showed Jennifer’s vehicle pulling into the parking lot at around 12:00pm on January 24. The driver remained in the vehicle for 30 seconds before exiting and walking by the pool area. Unfortunately, the image was too grainy for them to get a good look at the individual. The footage was sent to NASA for enhancement, but it didn’t help with identification.

The second camera caught the unidentified person walking along the outside of the apartment complex. Unfortunately, the camera only took images every two-to-three seconds, and in each the individual’s face was blocked by fence posts. The FBI was called in, but they were only able to determine the person was between 5’3″ and 5’5″, had large feet and was wearing clothing similar to that of a painter or manual worker. They were unable to determine their gender.

This unknown individual is considered the prime suspect in the case.

The day Jennifer’s car was found, search crews looked through the wooded area near Huntington on the Green. While items were found, none were related to the case. The search was continued into the weekend, with 1,400 people and search dogs looking for Jennifer.

At some point, someone contacted the police to say they’d seen someone matching Jennifer’s description riding in a white truck. It had pulled into a wooded area before leaving. While the area was searched by over 100 people, nothing was found.

In May 2007, Jennifer’s company offered a $1,000,000 reward for information leading to her whereabouts. It was active until July 4, 2007 and had the stipulation that she be alive. No one came forward to claim it. A $5,000 reward was also offered by Central Florida Crimeline for information leading to the location of her remains, but that too remained unclaimed.

A look into Jennifer’s cellphone records provided no clues as to her whereabouts, and it has been off since her disappearance. There has been no activity on her credit or bank cards.

In the hopes of bringing about new leads, the Kesses produced decks of cards with Jennifer’s image and description, and distributed them to local jails. In December 2008, a prisoner named David Russ claimed to have information he would only tell Drew. He turned out to be bluffing and had no knowledge regarding Jennifer’s disappearance.

In 2009, one of the detectives took a fresh look at the case. He interviewed a former housekeeper at the complex who had not been questioned back in 2006 and learnt the man on the surveillance footage resembled someone named “Chino”. Chino had lived in another building at Jennifer’s condo complex and was a former maintenance worker. Running his name through a leads tracking system revealed a tip about him had been called into the Orlando Police Department’s Crime Line just one week into the investigation.

Chino was arrested in 2008 for the statutory rape of a teenage girl, and he was in prison when the detective interviewed him. While he acknowledged doing work in Jennifer’s condo, he denied any involvement in her disappearance. He was given a polygraph test and passed. Jennifer’s father believes Chino is lying about his involvement.

The detective also re-interviewed another maintenance worker, as well as Jennifer’s building manager, but found nothing out of the ordinary.

The last official police search for Jennifer occurred in February 2014.

Jennifer’s car has since been returned to the bank, as it was a lease. It was given to the family after being examined by investigators, and they kept it garaged for a few months, in case it was needed. They currently have no information regarding its whereabouts.

Jennifer was declared dead by the state of Florida in 2016.

After years with no breaks in the case, the Kesses sued the Orlando Police Department for Jennifer’s files. They’d previously asked that the case be made cold, as more resources are available for such cases, but the police department refused, despite no leads being filed since 2010. They shared that they’d felt abandoned by investigators and believed no one had worked the case in years.

Prior to the files being handed over to the family, the then-police chief of the Orlando Police Department gave his team six months to work the case. They were unable to come up with any leads. Under the agreement with the Kesses, they are no longer leading the investigation.

In 2018, the Kesses were given more than 16,000 documents and 67 hours of video and audio recordings. They’ve since hired an investigative and legal team to go over the information and pursue new leads, and have conducted their own searches, with the aid of other law enforcement agencies.

The family hired private investigator Michael Torretta to work on the case. Upon reading the released files, he shared his surprise over what investigators did and didn’t do. One of the first things he did was return to Jennifer’s complex and speak with those who lived there. Many of the women shared they’d felt uneasy when the construction workers arrived.

The Kesses maintain a GoFundMe page to help fund their search for Jennifer.

There have been numerous reported sightings over the years, but Jennifer’s family doesn’t believe any of them were actually her.

Drew has personally written to every Foreign Embassy the United States has relationships with and asked that they make their military and law enforcement agencies aware of Jennifer’s disappearance.

In 2020, FOX News obtained exclusive evidence photos, which suggest a violent struggle took place on the hood of her car. According to Drew, it looks like someone was thrown down on top of the hood, and he hopes this will yield new leads.

Drew provided an update on the family’s investigation in July 2021, saying they’d revisited areas of interest and cleared them.

Jennifer is still considered missing and endangered by the Orlando Police Department, the Florida Department of Law Enforcement, the National Crime Information Center, the FBI, Orange County Police, Interpol and the NCMA. In June 2010, the FBI briefly took over the investigation from the Orlando Police Department, at the urging of then-police chief Val Demings, and Jennifer remains on their Most Wanted/Missing List. Investigators continue to receive and pursue leads, and it’s estimated thousands have been called in over the course of the investigation.

There is currently a $15,000 reward for information leading to Jennifer’s whereabouts.


1) Drew believes Jennifer fell victim to human trafficking, based on the fact that whoever abducted her only took her and not her belongings. Around the time of her disappearance, a major human trafficking organization was taken down in the Orlando area, which has only fuelled this theory’s plausibility.

Without evidence connecting Jennifer to a particular ring, investigators have very little to go on regarding this.

2) It’s Michael Torretta’s belief that Jennifer was abducted by one or more of the construction workers at the Mosaic at Millenia. This is based on his interviews with those who lived at the complex at the time, who said up to 10 workers were staying in an unlocked, empty apartment across from Jennifer’s condo. It’s Torretta’s theory she was attacked from behind while locking her door and dragged into the other unit. As the case’s initial investigators did not speak to those men and there was no official lease, it’s impossible to find out their names or locate them.

This theory is further fuelled by information Torretta learnt after the family obtained the police files. He says a witness saw a man in a pickup truck stop at Lake Fischer and dump a 6′ to 8′ carpet into the water on the day Jennifer went missing. The men working at the complex had laid carpet down that day. The family brought in a cadaver dog to search around the lake, and based on a hit a police dive team was called in. Unfortunately, neither the carpet nor Jennifer were found.

3) The final theory in the case states Jennifer was abducted after leaving her condo, either while walking to her vehicle or while driving to work. It’s believed she may have had a stalker who’d been watching her the morning of January 24, 2006 and decided to strike.

Unfortunately, due to how little evidence is available in the case, no one can be positive if this is the reason for Jennifer’s disappearance.


Five months after Jennifer went missing, Rob’s father died. He has since gotten married and started a family.

Jenifer’s parents have become advocates for families whose loved ones have gone missing. They’ve held numerous vigils over the years, and to keep her memory alive worked with the University of Central Florida to establish the Jennifer Kesse Criminal Justice Scholarship Fund.

Social media accounts, as well as a website, have been created to keep the public up to date on the investigation:

On May 2, 2008, The Florida House of Representatives unanimously passed Senate Bill 502, “The Jennifer Kesse and Tiffany Sessions Missing Persons Act“, to reform how missing persons cases are handled in Florida.

Logan was meant to move to California to be with his girlfriend a week after his sister disappeared. He put the move on hold to look for her. He travelled back and forth between Florida and California, and eventually obtained his real estate license. He has since gotten married and had children, and while he no longer lives in the area, he has no plans to stop looking for Jennifer.

Joyce says the hardest part about Jennifer’s disappearance is the limbo the family has been in, as they don’t know if she’s dead or alive.

Jennifer’s disappearance has been the subject of numerous podcasts and television series.


Jennifer Joyce “Jenn” Kesse went missing from Orlando, Orange County, Florida on January 24, 2006. She was 24 years old, and while what she was last wearing is unknown, it’s speculated she may have worn her three-stone diamond necklace. At the time of her disappearance, she stood between 5’8″ and 5’9″, and weighed approximately 120 to 130 pounds. She had shoulder-length, sandy blonde hair and dark-coloured eyebrows. Her eyes were green, but it’s been noted they may appear blue depending on her clothing. She wears clear contact lenses.

Jennifer has numerous distinguishing features, including a quarter-sized shamrock tattoo on her left buttock. She also has skin tags along the outside of her left hand; a defined cleft chin; a non-raised faded strawberry birthmark on her ribs; surgical scars along the inside of her left elbow; and a birthmark on the middle finger of her left hand, at the second joint down.

Currently, the case is classified as endangered missing. If alive, she would be 40 years old.

Those with information regarding the case are asked to contact the Kesse family tip line at 941-201-4009, the FBI’s Orlando field office at 407-875-9976 or FBI ViCAP at 1-800-634-4097. Tips can also be called into the Orlando Police Department at 321-235-5300, 407-246-2470 and 407-246-2959, or via its Crime Line at 1-800-423-8477.

Image Credit: Wikipedia/CBS News

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