Succession stories can turn out two ways; good or bad.
Before Caribbean hotel magnate Gordon ‘Butch’ Stewart transitioned to The Great Beyond, he wanted to ensure his succession story would follow his set storyline, a key part of which was carefully grooming the son he’d long-chosen and much-later publicly and legally will as his successor.
That Chosen One was Adam, who’s been Executive Chairman of Sandals Resorts International (SRI) since his dad died in New York on a frosty January morning in 2021.
You’d think that a wise and accomplished businessman who’s patiently built the region’s only Fortune 500 company over 40 long years into the Caribbean’s Leading All-Inclusive Company (a stature maintained for 25 consecutive years) would know what he’s doing, right?
Indeed, the evidence shows he clearly did.
January 4th (last Sunday) marked five years since SRI’s Founding Father departed — and since then, Adam Stewart has visibly re-invented and re-branded the brand to not-only keep pace with, but to also stay ahead of the surge of competition in the All-Inclusive niche.
Adam set the vision (as all leaders of worth do) and rallied SRI’s over 20,000 employees around and behind the concept of ‘Sandals 2.0’ — ushering an era of new growth and expansion that also saw the chain launch an award-winning marketing thrust under the banner ‘Made of Caribbean’.
Under Adam’s stewardship, SRI launched three new resorts: Sandals Curacao, Sandals Dunn’s River and Sandals Saint Vincent and the Grenadines (SVG) –the latter opening-up an entire new Caribbean market.
Sandals SVG has already been lauded as the World’s Best New Hotel and captured numerous awards in the two short years since it opened.
Located on the mainland with access to the Grenadine islands, Sandals SVG has become a prized jewel in the Sandals crown.
It’s also had a transformational impact on SVG’s economy and on the lives of its people – and there’s even-more on the cards, as SRI has long-announced plans for a Beaches SVG to introduce the Family Resort brand to the multi-island destination, joining Beaches Barbados and Beaches Exuma Bay.
In addition, Sandals is undertaking major upgrades to its properties throughout the Caribbean, even while occupancies are still very high that booking a Sandals’ vacation has to be done weeks (if not months) in advance.
SRI’s latest splendid achievement was the reopening – in less than one month — of five SRI Jamaica hotels badly-hit by Hurricane Melissa on October 28; and as promised, all were reopened before the 2025 Christmas holiday season.
So then, how could ‘Butch’ Stewart, looking down from above, not be proud and feel vindicated that he made the right choice?
But there are those who question the late Founding Chairman’s wisdom — among them his former wife Cheryl Hamersmith-Stewart, who has launched several legal challenges questioning Adam’s ability and capacity to run the company like his father visioned.
The US-based challenger has been seeking legal court rulings to address what it considers unfair and undue power by the Jamaica section over SRI, the parent company that runs the world’s most-successful family-owned luxury hotel chain.
Hammersmith-Stewart has claimed (in her latest case) that SRI can suffer serious financial losses under the present legal arrangements that see the chain run by an approved trust company.
She insists she has a case — and has been trying to win on several fronts, through different actions in US and Caribbean courts.
The challenger sought to have the Bahamas Supreme Court uphold a request to modify the composition of the current members of the trust running SRI, claiming the arrangement favoured Adam and the Jamaica branch of the family.
But the court ruled her lawyers’ arguments failed to convince the bench, which had ruled against her since October 17.
The Bahamas judges outrightly rejected Hammersmith-Stewart’s latest legal attempt to wrest ultimate control of SRI from Adam.
The successes outlined above obviously don’t impact Ms. Hammersmith-Stewarts certainty to continue pursuing her goal, until achieved.
Regional and international reporters following this interesting story tend to treat it as a movie-style rich family feuding saga with all the attendant thrills.
More-serious Caribbean observers – including journalists — would hope this latest judicial decision would be the end of the increasingly-costly seeming custody battle, but Mrs. Hammersmith-Stewart’s passionate and determined perseverance dims such bright expectations.
Meanwhile, SRI has so-far successfully repelled her continuing legal challenges.
SRI starts 2026 encouraged by the Bahamas Supreme Court’s ruling, but its Executive Chair and the chain’s directors are undoubtedly aware this is not the final chapter.
Mrs. Hamersmith-Stewart will no doubt pursue other cases in the legal and judicial pipeline that SRI has to continue preparing for.
Meanwhile, SRI’s over 20,000 employees at its nearly 20 properties across nine Caribbean territories may not realize their future can be decided by such court cases.
But Governments across the region well know they too stand to be impacted by the legal wrangling, which so far has proven to be vacuous — at best.
Fortunately, none of the cases seem to be in the realm of existential threats to SRI continuing to operate as the region’s best legacy business entity, as conceptualized by the proverbial Goose that laid its Golden Eggs.
Nor do Adam Stewart and the Jamaican side of the family treat the Bahamas case as an ultimate victory.
Aware of the other rivers to cross, Adam Stewart has been gracious and grateful.
Following the announcement of the Bahamas ruling on Tuesday, he told the press: “Despite the allegations being unproven, speculative and inherently flawed, they are being taken seriously and handled with due consideration,” by the Advisory Board, the trust running the chain and SRI’s Board.
SRI’s leadership understandably interprets the Bahamas court’s decision as vindication of its continuing successes under the current dispensation, but Mrs. Hammersmith-Stewart’s steadfast determination could have serious quiet but serious implications for the future of Caribbean’s tourism.
They say heavy is the head that wears the crown, but while the weight of these legal challenges would not be what the Sandals Executive Chairman would wish to carry today, he’s nonetheless carried it with grace.
Adam Stewart has remained clearly undeterred in his pursuit of a better future for his company, for his team members and their families and for the very future of Caribbean hospitality itself.
As a journalist who has followed and covered the Sandals journey over the decades and got to interact over time with, and better know, both ‘Butch’ and Adam, I for one have no reason to question the SRI Founding Father’s choice of successor.