Q+A Celebrity Connection: The Bad Boy of Hilton Head – Isiah Thomas

NBA legend Isiah Thomas on his legacy in the game, and his time on the island.

Story by Barry Kaufman

During this era of binge-watching docuseries, perhaps the only series that bows to “Tiger King” has been “The Last Dance.” Chronicling the rise of Michael Jordan to NBA legend, it does what every great docuseries does best: pulls the heartstrings, establishes a narrative and eschews any kind of nuance in favor of a neat and tidy story.


Such is the case with its characterization of the Detroit Pistons of the late ‘80s, the “Bad Boys” of the NBA and two-time champions. Because they were the foils to Jordan’s Bulls in the early years of Chicago’s dynasty, “The Last Dance” paints them as unruly, unsophisticated, unsportsmanlike monsters with extra emphasis on their hasty exit from the court in the 1991 finals.

But, add context, and you’ll find a team that made aggression its hallmark in an aggressive era in the sport’s history. They were tough; they were physical. But that was just how the game was played then. And if it was shocking to see them leave the court without shaking hands, was it any less shocking when Larry Bird did it four years prior?


“Hilton Head definitely has wonderful memories for our family. Family bike rides were almost a daily activity. Sitting on the beach in Palmetto Dunes at sunset was the best part of the day.” 
— Isiah’s wife, Lynn Thomas


“As people start to look back on what we did in the era we played in, I think people are starting to appreciate what a great team we were,” said former Pistons point guard Isiah Thomas. “We may not have felt the appreciation then, but we’re definitely being talked about more than we were in the last 15-20 years, which is good.”

WORST TO FIRST • Isiah Thomas puts up a shot against the New York Knicks in 1985 at Madison Square Garden. Thomas helped build a last-place Detroit Pistons team into back-to-back NBA champions in the late 1980s.

Coming off a spectacular season that saw him bring infamous Indiana Hoosiers coach Bobby Knight a championship in 1981, Thomas came to Detroit as the team was slumping hard. Around the 12-time all-star was built a legacy of championship basketball in Detroit that, to this day, requires nuance and context to truly appreciate.

“For a while we had a difficult story to tell because the narrative was that the NBA took off around the Celtics and the Lakers,” he said. “We say the NBA took off around the Lakers, the Celtics and the Pistons. We were the first team to start putting 50-60,000 thousand people in an arena. The highest-rated games of the ’80s were the Piston vs. the Celtics, The Pistons vs. The Lakers and the Pistons vs. The Bulls. All those highest-rated games have one thing in common – the Pistons.”

And during all those years establishing a legacy, Isiah Thomas would find his haven from the NBA spotlight on Hilton Head Island.

“We spent maybe 10-11 years there on Hilton Head. Mark Messier and the Messier family were our neighbors, so our kids grew up playing together. We had Messier on one side and John Cougar Mellencamp on the other.”

FAMILY Matters • Isiah is shown with his daughter, Lauren; his wife, Lynn, and his son, Joshua. For many years, the family owned a home on Hilton Head Island.

When he talks about his time on Hilton Head Island, Thomas doesn’t look at it in terms of the golf he played or the fish he caught (he admits to not being great at either, although he did both regularly) but of the memories he created during his time on the island.

“Phil Schembra, who sold us our house, gave me probably the best piece of real estate advice I ever heard,” said Thomas. “We were looking at it purely from a property value standpoint and he said, ‘You will never be able to monetize the family love and gathering that you will get from this house and from this island.’ And he was right. The priceless memories we have of Hilton Head to this day, and the friendships we had and the friends we’ve made are still very present in our lives.”


“We spent maybe 10-11 years there on Hilton Head. Mark Messier and the Messier family were our neighbors, so our kids grew up playing together.”
— Isiah Thomas


Even through the years that have passed, he still recalls the people he met here. His stories are peppered by such encounters as the trip to local designer and TV presenter Debi Lynes’ house.  “She had every kind of animal you can imagine in her house. When I say every kind, I mean porcupines, roosters, a raccoon that knew how to use the bathroom.” But his favorite stories revolve around his neighbor and the man Thomas calls “the greatest No. 11,” New York Rangers great Mark Messier. “A lot of our time on Hilton Head I spent with Messier talking sports, talking leadership, talking winning. At that time, he was winning championships, I was winning championships and we were just trying to figure out how to stay on top and keep winning.”

He would ultimately sell his home on Hilton Head Island as his career transitioned from the court to the front office to the broadcast booth and into the wider business world. Just as strong as his legacy in the game is his legacy as an entrepreneur, with his Isiah International firm investing in everything from real estate to waste removal.

FROM BASKETBALL TO BUBBLY • Thomas is the exclusive United States importer of the Cheurlin Champagne brand.

His latest venture takes him somewhat full circle. Winning back-to-back NBA championships, he was no stranger to the customary champagne shower. He’s back in the champagne business (in a glass, this time) as the sole importer of Cheurlin Champagne.

“As a family, we were looking at our next venture and when we looked into the spirits space, there was a new vodka, new tequila and a new wine every month. In the champagne space, we saw that most people couldn’t name five champagnes,” he said. “And the ones they could name all came from the same house.”

Looking beyond the standard bubbly, Thomas found Cheurlin on 200 acres of the oldest land in the Champagne region. The Cheurlin family has been in production since 1788, and one key difference helps their champagne stand out. Whereas most champagne you’ll find stateside comes from the second or third pressings, Cheurlin uses only the first, resulting in less sugar and sulfites.


“In the champagne space, we saw that most people couldn’t name five champagnes.”
— Isiah Thomas


“Knowing what I know now about champagne, I would never drink anything but the first press,” said Thomas. Along with bringing a better champagne to the market, Cheurlin is dedicated to keeping it affordable. “Even the second and third presses are outrageously priced. We don’t think you need to blow your rent money to get the best of the best.”

Cheurlin isn’t available in South Carolina yet, but you can find it through Cheurlin.com. Crack open a bottle, and raise a toast to a one-time local whose legacy as an entrepreneur, a philanthropist and an NBA great deserves nothing but the best.


Isiah Thomas facts & highlights

Born: April 30, 1961 (age 59)
Birthplace: Chicago
High school: St. Joseph (Westchester, Illinois)
College: Indiana (1979-1981)
NBA Draft: 1981 (2nd overall pick, Detroit Pistons)
Playing career: 1981-1994 (Detroit Pistons)
Coaching career: 2000-2012 (Indiana Pacers, New York Knicks, Florida International University)
Career highlights: NBA Champion (1989, 1990), NBA Finals MVP (1990), 12-time NBA All-Star (1982-1993), NBA All-Star Game MVP (1984, 1986), All-NBA First Team (1984–1986), J. Walter Kennedy Citizenship Award (1987), NBA assists leader (1985), No. 11 retired by Detroit Pistons, NBA’s 50th Anniversary All-Time Team, NCAA champion (1981), NCAA Final Four Most Outstanding Player (1981), Consensus first-team All-American (1981), USA Basketball Male Athlete of the Year (1980), McDonald’s High School All American (1979).

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