What happened to Leah Calabrese?

Judy Finkelstein said everyone in Winter Garden knew her daughter, Leah Denise Calabrese.

Calabrese was artistic, a loyal friend and stunningly beautiful. Everybody she met instantly liked her, and she would do anything for anyone in need.

It’s been more than 30 years since Finkelstein has seen her daughter. Not a day goes by that she doesn’t think of her. 

The last time Calabrese was seen was Oct. 24, 1992, in Winter Garden. She was only 29 years old when she went missing. She would now be 60. 

The Winter Garden Police Department is asking community members to come forward with any evidence or information that might help bring closure to the woman’s family and friends. 

Finkelstein is offering a reward of $10,000 for information leading to her daughter’s whereabouts.

“It is so devastating … you never get past this ever until you get closure,” she said. “It’s gut-wrenching, and it takes everything out of you. It’s this heavy load on your heart. It just sits there all the time. Sometimes, not too heavy, and sometimes, unbearable. If we could just know where her remains are, we could give her a proper burial that would be closure for our family.”

BACKGROUND

William Strickland, Calabrese’s father, filed an official missing/endangered person report for his daughter Nov. 2, 1992.

According to the report, Strickland said he dropped his daughter off on North Street by the intersection of 10th Street at about 10:30 a.m. Oct. 24, 1992.

Calabrese told her father she was going to help a friend clean her apartment.

She was last seen wearing an orange T-shirt and blue jeans. She is noted as having strawberry blond hair and green eyes. She weighed 110 pounds and was 5 feet, 7 inches tall.

Police files indicate Calabrese suffered from manic depression. 

Although she was observed to frequent the crime area on the city’s east side and occasionally would be out of touch for days at a time, she habitually called local family members during such times.

CRIME ANALYSIS

Sgt. Dave Clarke took over the case in 2012.

Clarke believes the department went above and beyond interviewing and reaching out trying to find Calabrese with no luck.

Clarke began his analysis by organizing the case file before beginning the process of having Calabrese entered into the National Missing and Unidentified Persons System March 2, 2012.

“People don’t understand how really hard it is to find a body,” he said. “Especially bones and things like that. She may be in a location or a state that doesn’t work with (the National Missing and Unidentified Persons System), or they don’t have the people to dedicate some time to research and say, ‘Hey, this could be your person.’”

Clarke said he discovered a photocopy of a letter dated Sept. 27, 1992, in which Calabrese wrote to her cousin Shannon Pollard while she was incarcerated.

The information was completed and Calabrese’s dental records also were sent to the NAMUS odontologist March 5, 2012. In addition, Finkelstein agreed to submit DNA samples.

At the time, Clarke said Finkelstein was convinced a previously employed Orange County Sheriff’s Office deputy by the name Henry Dean was responsible for her daughter’s disappearance.

Clarke began a preliminary investigation into Dean March 14, 2012.

The official offense report narrative filed by Clarke notes he traveled to the Orange County Sheriff’s Office Professional Standards Division to review Dean’s case file. 

Upon reviewing the file, Clarke discovered the possibility of Dean being a current law-enforcement officer in Louisiana. 

The file revealed Dean appeared to have several complaints from females alleging inappropriate behavior. It also showed Dean was a previous Monroe County deputy and had issues there with acting inappropriately toward females.

On March 16, 2012, Clarke spoke about Dean with investigator Judy Bollock, from the Grant Parish Sheriff’s Office.

Bullock advised Dean was a deputy in an adjacent parish until he was arrested and terminated. She said during his employment there, Dean pulled over an undercover state trooper who he solicited sex and drugs from during the traffic stop. He was subsequently arrested for the incident. 

On April 12, 2012, Clarke received a letter and newspaper article from Finkelstein regarding a female’s body being recovered in 1993 in Georgia. 

Clarke said the department frequently analyzed discovered bodies they thought may be Calabrese’s, but nothing yielded a match. 

On Dec. 14, 2012, Strickland died. 

SUSPECT SCRUTINY

Clarke said he never excludes anyone as a possible suspect, as long as there is sustainable evidence.

Calabrese was previously married and had a child — 5 years old at the time — who lived on the East Coast, but Clarke said the two were not in the picture at all. Calabrese’s parents and cousin also were never suspects. 

On Jan. 18, 2013, Clarke began looking into the last person to see Calabrese alive prior to her disappearance: Dean Hall. 

“They came up with an individual who was ‘trying to turn her around’ and was dating her,” he said. “You can read between the lines. … The evening before Calabrese went missing. … His story was he had dropped her off after a date, tried to convince her to quit her lifestyle and be with him … infatuation-type thing.”

Clarke began to conduct a thorough record check on Hall but was unable to find any information. He determined Hall had lied to the sergeant who was conducting the investigation at the time. 

Hall’s real name was Jerome Dean Hall, and his alleged wife at the time, Teresa Hall, was actually Tresa Rush, although the pair was never married.

Clarke said the department administered Hall a polygraph test, which he passed. However, Clarke noted he does not believe the tests to be substantial.

“It says he was honest, but he wasn’t even honest about who he was,” he said. “He passed the part where he said his name even though he lied.”

Rush also was noted to have two brothers.

In the letter Clarke recovered sent by Calabrese to Pollard from September 1992, he believes the brothers are mentioned.

“There was a letter that Leah had sent to her cousin about these two guys in a pick-up truck raping her, and this is prior to her missing,” he said “I tracked these two guys, and they actually lived in Winter Garden and had lied as well.”

Clarke then discovered Hall lived in Winter Garden at the time of Calabrese’s disappearance and not in Cocoa, as he had told the former sergeant on the investigation. He was listed as living in Winter Garden with his brother Bruce Foster.

Clarke went to meet with the property owner of where the brothers previously lived and searched the area for a possible burial site but found nothing.

He said he contacted the owner before the previous owner who advised she remembered two males living there when she owned the property but did not remember any names. However, she was able to recognize Hall in a photograph.

On Jan. 25, 2012, Clarke traveled to the Osceola County Jail, where he met with Pollard, who was incarcerated there.

When Clarke asked Pollard if she remembered Hall, she stated, “Oh, her stalker.”

Pollard said she recalled one morning coming home and being locked out of her apartment she lived at with Calabrese. While knocking on the door, Hall approached her and advised Calabrese was not at home and he had been waiting for her all night. 

Pollard never mentioned anything about Dean, the deputy.

“He was certainly a creep, and he was certainly weird and he certainly dated her when he was working but eventually he got fired for other things, and I tracked him all the way to Louisiana,” Clarke said of Dean. “(It is) highly unlikely he did anything because she was more where she wouldn’t go with him and kind of wanted to stay away from him as opposed to this other guy (Hall) (whom) she was with.”

Although Clarke said he initially thought Hall was the primary suspect, when the two brothers were discovered, he placed Hall on the back-burner. 

Hall died April 12, 2012. His brother Foster and his partner Rush also died.  

CASE CLOSURE

Finkelstein said she often talks to her grandchild, who is now 35, and his three children about her daughter. 

As of Clarke’s notes Oct. 28, 2019, there has been no additional information as to the whereabouts of Calabrese. All areas of notification are still active. He believes the case halted because there is nothing left to look at.

“Looking at this case, you know you get a lot of people who will say, ‘They didn’t look hard enough for her because she was of this certain type of behavior,’ because she had been arrested and was involved with drugs and such,” he said. “I can honestly say looking at this entire case that that is not the case at all. I mean, they put a lot of effort into this and did what they could do in that time period, especially with what technology they had compared to what’s available now.”

Clarke said he does not believe Calabrese is alive.

“A body is always really desired to have because if she’s found in Alabama or Louisiana where that deputy is, then I’m like, ‘OK I’ve been looking at these guys but this is the guy now because he’s been living in Louisiana and they found her in Louisiana,’” he said. “If they find her somewhere out here, then OK it’s more of a local connection because … this was all orange groves and dirt roads in 1992 … that’s the big thing, where’s the body? Because there could be evidence with that body.”

Clarke said the department has had instances where bones have been uncovered during development in the area.

“She’s here somewhere; we just haven’t found her,” he said. “Or unfortunately, these guys are plowing fields and orange groves and building houses; they just plowed right over her.”

Calabrese’s disappearance remains an open case, and although there has been no additional information as of now, Clarke said continuing to ask the community for help is essential.

“No. 1 is for her,” he said. “If she’s in the ground, in the dirt, that’s no place for anybody to be left. No. 2 is for mom. Closure.”