From Normandy to Maui: The Extraordinary Life of Robert “Pop’s” Sullivan

How a D-Day paratrooper’s grit and aloha spirit built a West Maui legacy spanning four generations — and one very legendary Jeep.

Some people find paradise. Robert “Pop’s” Sullivan earned it.

He was born January 12, 1923, in Saskatoon, Saskatchewan, Canada. He survived D-Day, the Battle of the Bulge, and three separate combat wounds. He was awarded France’s highest honor — the Legion of Honor — for his role in liberating the French people. He built a real estate business in West Maui from the ground up. He built a WWII Jeep from scratch with his bare hands. And for over five decades, he called Lahaina Town home.

This is the story of our founder. And it’s the reason everything we do at Maui Resorts by Sullivan Properties still carries his spirit.

A Young Man With a Dream — And a Problem

Robert B. Sullivan grew up in Salem, Oregon, and attended the University of Oregon — a proud Duck through and through. When World War II pulled the United States into conflict, Robert was a sophomore at the UO and felt the call to serve.

There was just one problem. He wanted to fly.

The US Air Force turned him away — he was colorblind. Undeterred, Robert learned that a friend had successfully enlisted as a pilot through Canada, where the standards were different. He crossed the border in Seattle with six other men.

Canada turned him away too. Still colorblind. Six of the seven men were accepted. Robert was the only one left standing outside.

If You Can’t Fly — Jump

Most men would have gone home. Robert Sullivan decided to stay in Canada and find another way. The closest thing to flying he could find was jumping out of planes. He volunteered to be a paratrooper with the 6th British Airborne Division, 1st Canadian Parachute Battalion.

That single decision — made by a stubborn, colorblind kid from Saskatchewan who refused to quit — would change history. And eventually, it would change West Maui real estate.

“The closest thing I could find to being a pilot was being a paratrooper, so I volunteered to do that.”

— Robert “Pop’s” Sullivan

The Night of June 5th, 1944: Into the Darkness Over Normandy

On the night of June 5th, 1944 — the eve of D-Day — Robert Sullivan climbed into a C-47 aircraft and flew low over occupied France. Troops were, in his own words, “just scared as hell,” as German anti-aircraft fire — the “ack, ack” — lit up the sky around them. When the green light came on, the men made a mad dash to get out of the airplane.

Pop’s jumped into the darkness armed with grenades, a stiletto knife strapped to his leg, and a Sten gun — a British submachine gun holding 22 rounds of .30-caliber ammunition.

“Well, I’m coming down, and it’s darker than hell. There were trees all around and a house. And I whacked into the side of the house and down on the ground I went with this big crap all over me. And I thought, ‘Holy Christ, the whole German army’s going to come out and get me.’”

— Pop’s Sullivan, recalling D-Day to The Maui News, 2014

Instead, he found other paratroopers — many of them lost, scattered behind enemy lines. They survived an intense Allied bombing run by jumping into a creek ditch. For the next two to three months, the Canadians were in nearly daily combat, suffering horrendous casualties.

Pop’s was wounded three times. Once, mortar shrapnel hit him and embedded itself in his back. He carried it for the rest of his life — and joked for decades that he knew it was there because he’d set off metal detectors at airports.

He then fought in the brutal Battle of the Bulge in the bitter cold of Rochefort, Belgium. “Everybody burned their boots to try to keep warm,” he said. After transferring into the US Army and earning the rank of sergeant, he was training soldiers when the war finally ended. He later served in the Korean War as a US Army first lieutenant. 

Chevalier — Knight of the French Legion of Honor

1st Lt. Robert B. Sullivan — Legion of Honor Recipient. Rifleman, 1st Canadian Parachute Battalion, 6th Airborne Division (British).

In 2017, the President of the French Republic bestowed upon Robert B. Sullivan one of the highest honors a nation can give — the Legion of Honor, the oldest and most prestigious French order of merit, created by Napoleon Bonaparte in 1802.

The Consul General of France wrote to Pop’s at his home on Wainee Street in Lahaina:

“By decree of the President of the Republic of France, you are appointed a Chevalier (Knight) of the National Order of the Legion of Honor. This award testifies to the President his high esteem for your merits and accomplishments. In particular, it is a sign of France’s infinite gratitude and appreciation for your personal and precious contribution to the Allies’ decisive role in the liberation of our country during World War II. The French people will never forget your courage and devotion to the great cause of freedom.”

— Emmanuel Lebrun-Damiens, Consul General of France, July 7, 2017

The Legion of Honor medal awarded to 1st Lt. Robert B. Sullivan — République Française — presented by the Consul General of France.

The official letter from the Consulat General de France, San Francisco, July 7th, 2017 — addressed to Mr. Robert Sullivan, 550 Wainee Street, Lahaina, HI.

France never forgot what Pop’s did on that dark night over Normandy. Neither will we.

The first Sullivan Realty office window in Salem, Oregon — loans, insurance, homes, farms. Whatever his community needed, he was there.

Back to Oregon — and Back to Work

Robert Sullivan came home, finished his business degree at the University of Oregon in 1949, and got to work. At 27 years old, he started Sullivan Realty in Salem, Oregon. He sold his first home for $6,500.

He married Paula Ann Smith, and together they built a family: sons Tim, Pat, John, and Mike, and daughter Molly. Then in 1962, the Columbus Day Storm — the most powerful extratropical cyclone to ever slam the Pacific Northwest — sent the Sullivan family looking for calmer skies. They moved to Hawaii, first settling on Oahu where Robert ran several businesses. In 1969, the Sullivans made their final move: to Lahaina Town, Maui, buying a home on Wainee Street.

Maui had called. And the Sullivans answered for good.

Building West Maui — From Kapalua to Lahaina

Robert Sullivan didn’t just move to Maui — he helped shape it. In 1975, he was one of only three brokers selected by the Kapalua Land Company to sell the original offerings at Kapalua Resort — The Bay Villas, The Golf Villas, The Ridge Villas, and the Ironwoods. He was also involved in the development of homes at Wahikuli, Puna Point, and Mahana.

In 1979, he founded Lahaina Towne Brokerage in historic Lahaina Town. It became Sullivan Properties in 1988, when his son Patrick T. Sullivan joined him. What started as a real estate brokerage grew into the full-service vacation rental and property management company you know today as Maui Resorts by Sullivan Properties.

Pop’s lived on Wainee Street in Lahaina for five decades. He was woven into the fabric of this town in every way that matters — and nowhere more than at the Lahaina Yacht Club, his favorite gathering spot, where he could be found faithfully every Friday. It was there, among friends, fellow veterans, and the West Maui community he loved, that Pop’s truly held court. Lahaina was never just a business address to this family. It was — and always will be — home

The Jeep on Wainee Street

If you ever drove down Wainee Street in Lahaina, you may have spotted it: a fully restored WWII-vintage Jeep sitting proudly in Pop’s front yard, olive green with white stars and U.S.A. painted on the hood.

That Jeep wasn’t bought. It was built.

Godfrey — a Lahaina legend and longtime beloved figure at Kimo’s restaurant — decided to take a well-earned sabbatical. Pop’s son John Sullivan happened to be Godfrey’s best friend. So that summer, the two of them did what any self-respecting West Maui man would do with a little free time: they built a WWII Jeep completely from scratch, piece by piece, right there on Wainee Street.

It sat in Pop’s front yard for five decades as a tribute — to the war he fought, the freedom he helped defend, and the Lahaina life he built on the other side of it all. Sadly, the Jeep was lost in the 2023 Lahaina wildfire. But it remains forever etched in the hearts of Lahaina and the Sullivan family.

That’s Pop’s Sullivan in one story.

Pop’s Sullivan (left) with fellow WWII veteran Walter McKinney of Oregon — always at his favorite spot, the Lahaina Yacht Club. Two men who gave everything and then chose paradise.

Four Generations of Aloha

The Sullivan legacy didn’t stop with Pop’s. Patrick T. Sullivan — who also attended the University of Oregon, earning his degree in real estate and finance — is now Owner and Principal Broker of the firm. His daughter Kelly Johnson works as a real estate agent, carrying the family tradition forward with pride. His son Kevin P. Sullivan runs a professional surf lesson business on Maui — teaching many of the company’s vacation rental guests to ride the waves — and has also begun his real estate career within Sullivan Properties.

Pop’s left behind four children, 16 grandchildren, and 16 great-grandchildren. Four generations of the Sullivan family have now called Maui home. The roots go deep.

From Saskatchewan to Salem to Lahaina. From a $6,500 first home sale to a portfolio spanning Kaanapali, Kahana, Napili, Kapalua, and beyond. From a C-47 over Normandy to a hand-built Jeep in the front yard on Wainee Street. This is what four generations of dedication looks like.

Honoring Those Who Serve

In honor of Pop’s Sullivan — D-Day veteran, Battle of the Bulge survivor, Korean War lieutenant, and Knight of the French Legion of Honor — Maui Resorts by Sullivan Properties is proud to extend a special military discount to all active duty military and veterans who stay with us.

Because that’s what Pop’s would have wanted.

The Spirit Lives On

When you book a vacation rental with Maui Resorts by Sullivan Properties, you are not just booking a condo with an ocean view. You are becoming part of a story that started with a colorblind kid from Saskatchewan who refused to take no for an answer, jumped out of a plane over Normandy in the dark, and eventually found his way to the most beautiful place on earth.

He built something here. And we take care of it — and take care of you — because Pop’s taught us that’s what you do.