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Dennis ‘3 Olive’ Winnie — a bittersweet tale

By Staff | Nov 24, 2011

Veteran Dennis Winnie, who smiled all the time but rarely in photos, wears a Purple Heart received by his dad and his own medals from World War II.

KAANAPALI – Dennis J. Winnie, 88, a much decorated veteran, devout Catholic and ubiquitous figure who strolled through Whalers Village every day for years, passed away in Italy this summer and faced burial in a pauper’s grave there. An attorney, the courts and Maui friends intervened.

As told to this columnist by friends Tom and Tammy Vanderlaan, who spend seven months a year on Maui, Dennis died of cardiac arrest in his sleep in the Excelsior Hotel in Siena, Italy. He journeyed there despite having just recovered from walking pneumonia. His many friends cautioned him not to go, but he insisted if anything happened, his affairs were well-organized. Indeed, he may have seen that the end was coming.

This is a tale with a bittersweet ending. The story embraces the aloha spirit, with Maui friends stepping up. But it also reflects the insensitivity of two Mainland relatives who rejected – or, charitably, did not know of – his wish for a burial on Maui. They also failed to even send an obit to local papers, even thought their father was well-known here. This is being left to friends. Voices of Maui today addresses this omission.

Dennis became a permanent resident of Maui 18 years ago, falling in love with the islands after stints as an accountant in Honolulu. Employed by Paramount Pictures, the accountant worked on the sets dispensing cash for the 1970s and ’80s TV shows “Hawaii Five O” and “Magnum P.I.”

Owner of two pricey condominiums (including The Whaler), Dennis was a regular at Hula Grill, where he would arrive every day to imbibe what he called “desert martinis” – Bud beers with three olives in them, Vanderlaan recalled. The olives were always placed in a napkin for the trip home.

Dennis loved Lahaina’s Halloween. “We had standing reservations at Kimo’s for eight or nine years with eight or nine of us,” Tammy reported. “Dennis would always go along.”

One year, he dressed up as a drag queen Dracula. Tammy happened to sit next to him at Kimo’s but did not recognize him until she spotted three olives in his glass.

“Dennis?” she queried.

“No, it’s Denise,” he quipped.

Tammy remembers Dennis as “a wonderful, wonderful man a loving man. He loved people and the culture. I can’t say enough about him. He was part of my life. He was more of a giver than a taker. Every year, he remembered Tom’s birthday and many others. He loved to travel and would go to Australia almost every year.”

He was friendly with people from Germany and the other countries he traveled to, as well as those from foreign lands he met here.

“Mostly he kept to himself,” Tammy said, but he would show up for brunch at the Kaanapali Beach Hotel every Sunday. His favorite hangout, however, was Hula Grill, where she said “he would sit on the same stool, seven days a week, precisely at 3:45 and stay until 4:45.” After the first “martini,” he’d pour the olives into his next glass.

Hula Grill General Manager Orrin Cross noted that “Dennis always had a smile on his face. He’d send me postcards on his trips, but he drove up my costs with all those olives.”

Passerby and parishioner Dawn Balog remembers him on Veterans Day, decked out with his many medals from his World War II Merchant Marine service, where he appears to have won a Purple Heart.

A devout Catholic, Winnie opened Maria Lanakila Church for 17 years every day at 5:30 a.m. He’d serve as a greeter and reader at the 7 a.m. mass.

On Saturdays, according the Vanderlaans, he would limit himself to one drink instead of three if he happened to be going up to the Kapalua Chapel to read at the evening service.

Pastor Gary Colton called his long service with the church exceptional. “After opening, he’d read his prayer book and maybe take a nap before start of mass.”

Tom reported that Dennis would always shake hands with him when he left the bar with his three olives in a napkin before taking the shuttle (Kaanapali Trolley). He would eat them on his way to his home at Kaanapali Villas, undeterred by the food ban on the trolley.

Normally, when he shook hands, he would transfer the olives from his right hand, always saying to Tom that “you’re not going to get my olives!”

Four or five years ago on his way to Australia, he shook hands without making the transfer, and the olives were crushed in the handshake.

“I wondered whether he was checking out on me,” Tom said.

Despite owning two condos, perhaps worth a million or more, Dennis was headed to a pauper’s grave in Italy until the Hula Grill gang intervened. The employees cobbled together $10,000 to bring back his remains that had been languishing in storage facilities.

The group got him back to the U.S. this month. A court order opened up his Whaler unit, and discharge papers needed for military burial were found.

His wish, friends said, was to be buried at the Veteran’s Cemetery in Makawao.

Dennis told many friends he wanted to leave his assets to the church, but with no will found, that appears to be unlikely.

Dennis will get his due Dec. 2, when Maria Lanakila holds a 6 p.m. Visitation, followed by a Memorial Mass. The Vanderlaans expect the church to be packed.

Today Dennis rests – but not entirely at peace – in Grave 33-2312 at a military cemetery in Long Island, N.Y., 4,000 miles from his chosen burial site.

Parishioners pointed out, according to Father Colton, that he died close to Rome, the center of the church. Perhaps that was his plan.

Columnist’s Notebook: Hard to say if justice can be done, but it would be nice to have Dennis back here where he belongs. Maybe the community will have something to say about that.