IE 11 is not supported. For an optimal experience visit our site on another browser.

Sister looking for clues in September 2021 disappearance of Kevin Winters from Maui, Hawaii

The 51-year-old was captured on security footage on the morning of September 3, 2021, making a deposit at the First Hawaiian Bank in Kahana, Maui, Hawaii. He hasn’t been seen since.

It’s been over 10 months since Kevin Winters was last seen in Maui, Hawaii. He was captured on security footage on September 3, 2021, depositing a check at the First Hawaiian Bank in Kahana, Maui.

He hasn’t been seen since.

“Distance had never changed anything as far as our bond,” Karen Hopp told Dateline about her older brother Kevin Winters. Karen and Kevin were the “middle children” of the Winters family, with one older brother and one younger brother. They grew up in Jennison, Michigan and, according to Karen, the family was extremely close and would often go on adventures together. “We did a lot of camping,” Karen noted.

Karen told Dateline that Kevin, in particular, spent a significant time outdoors. “He did dirt biking,” Karen said. “When he was a teenager, he got in an accident.” She added that because of that accident, Kevin’s right leg is shorter than his left.

In 2007, Kevin decided to leave Michigan living behind and head to Hawaii. “He’s always wanted to go someplace warm,” Karen said. But he “never came back.”

Kevin Winters in Hawaii.
Kevin Winters in Hawaii.Karen Winters

Karen told Dateline her brother immediately fell in love with Hawaii. “He has local bars he’d hang out at,” Karen said. She added that her brother was “super happy” and “enjoying life.”

A year after making the big move, Kevin secured a job working at the North Shore Hostel in Wailuku, a town in Maui. “He was living and working there in exchange -- basically in exchange for his room,” Karen told Dateline.

But after 14 years, in late August 2021 Kevin, then 51, lost his job and a place to stay. “He was supposedly terminated for stealing a phone,” Karen said. She added that her brother would never do that. “He was given like seven days or something like that to move out,” she said.

On September 1, Kevin was moving out. Karen said she is unsure of where exactly her brother was moving to, but said he had a storage unit down the street from North Shore Hostel, where he was known to stay sometimes. “He had a garage that had his Jeep in it with a couch,” Karen said.

Karen told Dateline that her brother’s Jeep wasn’t running and had been sitting idle in the storage unit for over a year, so he would typically get around on foot or by bus.

According to Karen, the next day, on September 2, her brother visited Maui Brewing Company in Kahana, Hawaii, about an hour away from his storage unit in Wailuku. “He was there at 8:37 p.m.,” Karen said she found this information from Kevin’s bank history. She added that at 9:45 p.m., Kevin was captured on security footage depositing a check at an ATM at the First Hawaiian Bank near the brewery in Kahana.

Karen told Dateline that Kevin and their mother, Maxine Winters, are extremely close and speak every day. She said her mother spoke with Kevin on September 2, and everything seemed normal. Karen described the conversation as “short and sweet.”

Karen told Dateline that Maxine sent Kevin about $140 each month to cover his living expenses. But Karen said she found it unusual that Kevin would be depositing money. “That was not normal behavior,” Karen said. “I was looking at his statements and I’m like, ‘He rarely even made a deposit.’” Karen said that the check he deposited that evening was for $40.

Kevin Winters at the First Hawaiian ATM in Kahana, Maui on September 3, 2021.
Kevin Winters at the First Hawaiian ATM in Kahana, Maui on September 3, 2021.Karen Winters

The next morning, on September 3, 2021, security footage captured Kevin making another deposit at the same ATM, in the same clothing. Karen said this time it was for $190. “He made two deposits and then vanished,” Karen said.

That was the last time anyone saw Kevin.

After days of no communication from Kevin, Karen said her parents started to worry and called her on September 8. “My dad called and said, ‘Whoa. This is unusual. Why haven’t we heard back from him?’”

That day, Karen said her parents called the Maui Police Department. She added that “for some reason, the missing person report wasn’t filed until September 19.”

The Maui Police Department is investigating Kevin’s disappearance. On September 20, 2021, they posted on their Facebook Page that Kevin was “reported missing on the afternoon of Sunday, September 19, 2021.” It adds that “his family reported the last contact with him was on Thursday, September 2, 2021.” It also notes that they are “requesting the public’s assistance with any information on the whereabouts of Kevin Winters.”

Dateline has reached out to the Maui Police Department multiple times within the last two daysbut has yet to receive a response.

Karen told Dateline that since none of her family lives in Hawaii, it was initially difficult to look for Kevin. She said all of the correspondence they had was with one friend of Kevin’s, and with detectives who, according to Karen, were not helpful. “Detectives kept saying, ‘Maybe he, you know, went on a bender or something,’” Karen recalled. “’Or maybe he fell asleep or died contracting Covid.’” But Karen said she was not interested in hearing the theories they offered. “The detective had a different picture he wanted to paint.”

On November 9, 2021, Karen said she and her husband flew to Hawaii to look for Kevin themselves. “Just to see if there were any clues or anything,” Karen said.

Kevin Winters outside a bar he frequented.
Kevin Winters outside a bar he frequented.Karen Winters

Karen told Dateline they went to the bars Kevin frequented, and bartenders all told her the same thing: that Kevin was a nice guy and “always had two drinks -- a vodka cranberry.” She added that the information from the bartenders was a clear indication to her that Kevin was not a “drunk.” Karen said while they were there, they also put missing persons’ flyers up around town.

Karen told Dateline she believes foul play is involved in her brother’s disappearance. “If you were going to go missing, why would you not be withdrawing everything you had?” she said, pointing out that Kevin still had $1,200 in his account.

Karen said she won’t stop looking until she finds out what happened to her brother. She runs the ‘Find Kevin Winters’ Facebook page dedicated to tracking down any leads that can help find Kevin.

Karen said that their mother is suffering from health issues, but has not stopped hoping for her son’s safe return. “My mom -- she’s struggling,” Karen said. “Every single day she will text or call and say, ‘Have you heard anything about Kevin?’”

And every day Karen has to tell her no.

Kevin is 5’10” and 160 lbs. He was last seen wearing a white collared shirt, blue jeans, and black dress shoes. Karen noted that one of the shoes Kevin was wearing has lifts because of his right leg being shorter than his left. She added that Kevin has a “super sweet smile,” and described him as “handsome.” Kevin would be 52 years old today.

Kevin never married, did not have children and it is unclear if he was dating anyone at the time.

Anyone with information on Kevin Winters is asked to call the Maui Police Department at 808-244-6400, Karen Hopp at 616-403-4552 or and Kurt Winters at 616-581-5736.