The Disappearance of William “Billy” Smolinski Jr. (Connecticut)

For over 20 years, the Smolinski Family has been searching for their son and brother, Billy, who one afternoon in August of 2004 asked his neighbor to watch his dog and then was never seen again. The case is not without leads or suspects, but the biggest question of all has yet to be answered: Where is Billy?

August 24, 2004

It was around 5 p.m. on the evening of August 24, 2004 when 31-year old Billy Smolinski Jr. left his neighbor’s house on Holly Street in Waterbury, Connecticut. Brynn Mandel reports for the Republican-American that Billy had stopped by to ask his neighbor a favor. He was heading “up north” for three days to go see about a car he was interested in buying and wanted to know if the neighbor could look after his dog while he was away.

Billy’s dog, a German shepherd named Harley, was like a child to him. According to reporting by John Murray, who has covered this case extensively for The Waterbury Observer over the last 20 years, Billy got the dog with an ex-girlfriend, Mary. They’d dated for eight years and even though the two had broken up, they stayed close friends and she and Billy both continued to care for Harley together. In fact, she had watched Harley while Billy was on vacation in Florida just the week before, but this time, Billy’s neighbor agreed to take care of the dog.

On the morning of August 25, it was Mary who was first alerted that something weird was going on when she got a concerning call from Billy’s neighbor. He explained that Billy asked him to take care of Harley, but he couldn’t find a key and Billy was apparently gone already and the dog was still inside Billy’s house. This immediately struck Mary as odd. He definitely would not have left Harley behind unattended or taken off somewhere without letting his family know where he was going.

So, Mary called Billy’s sister Paula to see if she knew where Billy had gone, but this was the first Paula had heard that Billy was going anywhere…She, too, got the sense that something was off. Paula called her parents, Janice (who went by Jan) and William “Bill” Sr. and they all went to check on Billy’s house on Holly Street.

Michelle Tuccitto Sullo reports for the New Haven Register that when they pulled up to the house, Billy’s mother, father and sister immediately noticed that Billy’s white Ford pickup truck was there but it wasn’t where Billy usually parked it. It was down at the end of the driveway almost blocking the entrance, not pulled up close to the house. It was a big red flag. Their first thought was that someone else had driven Billy’s truck. His family checked on Harley and then wasted no time going straight to the Waterbury Police Department to report Billy missing.

But when Jan, Bill and Paula tried to get help from local police, they were told they had to wait before any report could be taken. Billy told his neighbor he’d be gone for three days, so until then, they couldn’t report him missing. He’d probably come back just as he said he would, and this would all be a misunderstanding.

While the Smolinskis waited for that three day mark, they tried finding Billy on their own. They talked to neighbors and friends and looked through his house to see if they could find any clues as to where he went. All they could find was a Burger King receipt in his trash can. It was timestamped 2:59 p.m. on August 24, the day he disappeared, which was a few hours before he stopped by his neighbor’s house to ask about watching the dog. Jan and Paula went to Burger King to see if the security camera footage captured Billy there – maybe he was with someone when he ordered his food – but the footage from the 24th had already been overwritten by the time they got there.

Finally, on August 27th, the Waterbury Police Department took a missing persons report for Billy Smolinski Jr. That was when the police investigation into his disappearance officially began.

Billy is Missing

Waterbury PD issued a BOLO with Billy’s name and description and then took a few preliminary investigative steps, like checking Billy’s bank account and financial records for any activity. There were no transactions in the days since he last had contact with anyone.

Meanwhile, Billy’s family amped up their own efforts and foot searches. Paula called everyone she could find in Billy’s personal phone book but no one had seen or heard from Billy since the 24th. Billy supposedly told his neighbor he was going “up north” so Paula called the only person she could think of that Billy might know “up north” – an old friend from New Hampshire – but he hadn’t talked to Billy either.

Dozens of volunteers joined his parents and sister to scour the banks and waters of the Naugatuck River and wooded areas near his house. According to a supplemental report for Waterbury Police Department Case No. 2004-071025, on August 31, Billy’s uncle was out searching the woods off Longmeadow Drive in Waterbury when he noticed a foul odor. It was a spot where Billy and friends used to hang out and drink beer when they were younger. Paula reported this to Waterbury PD and detectives responded to the location to search for the source of the smell, but didn’t find anything that might be related to Billy’s disappearance.

After checking the woods, reports show that the detectives stopped into Billy’s house and spoke with his neighbor who was one of the last known people to see and talk to Billy. The neighbor told police that yes, Billy asked him to take care of his dog and that he said he’d be gone for three days, but Billy never left a key and the neighbor didn’t know where Billy might be. However, the neighbor told the detectives something else…That evening when Billy stopped by, he shared with his neighbor that the vacation he just got back from hadn’t gone so well – he and his girlfriend broke up.

For about a year, Billy had been dating 51-year old Madeleine Gleason, who worked as a school bus driver for a transportation company in Bethany, Connecticut. Hearing that the relationship ended just two days before his disappearance, detectives gave Madeleine a call. It appears the conversation was brief. Madeleine explained that Billy had broken up with her because he thought she was cheating on him. She also stated that she saw Billy on the morning of the 24th…He showed up at her house early in the morning and asked Madeleine to get back together, but she needed time to think. She said when Billy left her house, he was, “A little depressed.”

So, he was having relationship problems, and detectives also learned that Billy was recently laid off from his job as an apprentice for a heating and air conditioning company. Investigators considered the possibility that Billy could have taken off for some time alone or even that he harmed himself, but his family strongly denied any suggestion that Billy was missing because he wanted to be.

Until they found Billy though, every theory remained on the table.

Early Investigative Leads

According to case file documents, on September 3, Waterbury PD executed a search warrant for Billy’s home phone to review the call log for August 24. Detectives found that among the calls Billy made that day, he dialed  one number three consecutive times: Twice within the same minute at 11:44 a.m. and a third call at 11:58 a.m. Those were the last calls Billy made from his landline the day he disappeared. Police traced the phone number to a man I’ll call by a fake name, Jacob.

Investigators tried to contact Jacob that same day, September 3, leaving several messages for him to contact Waterbury PD, but they didn’t hear back from him for over a week. When detectives finally received a call back from Jacob on September 13, he agreed to come in for an interview.

During that September 15th interview, the detective asked Jacob how he knew Billy Smolinski. He explained that his father was business partners with the owner of a transportation company where a mutual friend of theirs worked. That “friend” was Madeliene, Billy’s girlfriend, or I guess, ex-girlfriend at that point. Jacob knew that Billy and Madeleine had dated for about a year but he said he didn’t have any personal interaction with Billy.

The detective asked Jacob if he’d ever had any trouble with Billy and Jacob said no, but then the detective pressed him a little more and Jacob finally admitted that he was having an affair with Madeliene, and Billy wasn’t happy about it. Jacob told the detective that he was hesitant to say anything because he was married and didn’t want it to get back to his wife that he stepped out on their marriage.

As the interview progressed, the detective broached the subject of phone calls that Billy made on the day he disappeared. Jacob said at first that he hadn’t gotten any calls from Billy but then said he did receive a message from an unidentified man. The caller said, “You better watch your back at all times.” Jacob told the detective that he still had the tape and agreed to turn it over to police the next day.

When detectives reviewed the answering machine tape, they heard the same message that Jacob described. In an attempt to identify the caller, the detective contacted Billy’s sister Paula who confirmed that the voice was her brother, Billy. With that, the tape was retained as evidence in Billy’s case.

From the very first day of the official police investigation, Billy’s family had pressed detectives to process his truck for fingerprints and other evidence. They were sure that Billy wouldn’t have parked it at the end of the driveway and if someone else had driven it as they suspected, their prints might still be there. According to Billy’s family, they were told that it was “too late” to do anything with the truck, but about two weeks later a detective finally went through the cab. Shoved deep behind the seat, the detective found Billy’s wallet and keys. For Billy’s family, it was even more proof that Billy hadn’t left on his own.

Billy’s story continues on Dark Downeast. Press play to hear the full episode wherever you get your podcasts.