A conversation with … Dale Crighton

In the Cayman Islands, where the political climate often dictates a paradigm of “you’re either with me or you’re against me,” it takes a particular kind of person to stay on the good side of every government. Caymanian Dale Crighton is that kind of person.  

The affable Crighton has been appointed to statutory boards of various governments since returning from college in his mid-20s, and in recent years, he has been appointed to boards by both the United Democratic Party and People’s Progressive Movement administrations. 

“Well, I’m friends with both governments,” he says. “I’m not a member of either party because I’m friends with people from both sides. I think each party has something to offer. You got smart guys here, you got smart guys there.” 

Over the past 20 years, Crighton has sat on numerous boards, including the Planning Appeals Tribunal and the Trade & Business Licensing Board, on which he has served as both chairman and deputy chairman. Currently he is chairman of the Information and Communications Technology Authority board.  

Coerced initially into sitting on boards by his father Rex, Crighton learned early on the benefits of staying politically neutral. 

He remembers one time in the 1990s when he was sitting on a committee for MLA McKeeva Bush and simultaneously working with MLA Truman Bodden on another committee, and that the two were bitter political rivals at the time. 

“I would get lambasted,” he recalled with a laugh. “I would go and meet McKeeva and he’d say, ‘How’s your friend doing?’ and then I would go to a meeting at Truman’s house… and Truman would say, “How is your friend doing?’ And I’d say, ‘You know what, he just asked me the same thing.’” 

Over the years, Crighton has seen the nature of government boards change.  

“Honestly, I can say years ago people were appointed to boards just for political purposes, and maybe it’s done to a certain point the same today, but I can tell you that more recently, people have been appointed to boards that I’ve been involved with, not particularly with regard to who they are and who they voted for, but for what they can do.” 

Sitting on the boards is a way of providing service to the country, and while it might carry a certain amount of prestige, it also comes with a degree of personal danger. Crighton remembers well the first time he realized the danger. It came when a decision by the Planning Appeals Tribunal was challenged in court. 

“The members of that Tribunal made a decision based on what they thought was right and not what was right by law,” he said, adding that their decision also might have been tainted by relationships. “Up until that point, everyone thought, ‘well, we could do whatever we want; we don’t have to worry.’ But the fact is, if you’re on the board, you’re liable personally as well. And that’s when it sunk in – when Judge [Henry] Graham said, ‘if you all come before me again, I’m going to prosecute each one of you individually.’ And then he laid everything out to us and that woke me up.” 

Crighton said there is also social liability from sitting on government boards. 

“You’re making a decision on people,” he said. “It’s a small island and everyone knows you’re on the board, and if you’re making a decision that affects them negatively, it comes back on you, even if you say, ‘you know what, so and so is my friend, I’m going to recuse myself.’ It still comes back on you. 

“So it’s a position not to be taken lightly, but we have to have good people in those positions because if not, everything shuts down and we don’t grow as a country.” 



Perhaps the reason Crighton has been a consistent choice of various government administrations to sit on statutory boards is his pragmatic business approach that is untainted by political concerns. In September 2012, he was appointed by the UDP government as chairman of the Information and Communications Technology Authority board, and in August 2013, after the May 2013 elections changed the government, he was reappointed to the position by the Progressives-led administration.  

With the ICTA facing some important decisions in 2015, Crighton said he is glad to have the board he now has, which he thinks is the best one he has ever been a part of. 

“The main thing is you have to good board, you’ve got to have people who can contribute and not people who just constantly object for the sake of objecting,” he said.  

One of the decisions facing the ICTA now is on the content of licensees, both in terms what is acceptable and how much of it should be locally produced. Crighton gave some insight into his thinking on the latter subject. 

“There’s a couple of schools of thought,” he said. “Number one, basically everyone…is going to be transmitting the same information – HBO, Cinemax – same stuff. What is going to dictate who has the most customers? Well, obviously pricing and additional content.” 

Crighton said licensees will have to add more local content to stay competitive, and that marketing initiatives can only take a company so far. 

“You’re going to pay the same thing for HBO as the other guy and you can only drop your price so far, so what’s going to make you more attractive than the other guy? It’s… who is going to have the best local content? Who is broadcasting the CONCACAF Under-15 Cup in Cayman in 2015? Who has rights to that? That is going to dictate who gets market share.” 

By letting the market dictate local content rather than using a heavy regulatory hand, Crighton thinks it will create competition. 

“By creating competition like that, people are going to say, ‘You know what, I need to add more local content to be competitive.’ It’s good for the consumer; it’s good for business.” 


Real estate roots  

Although he is involved in numerous businesses including Equipment Ltd., Dolphin Discovery Cayman, The Security Centre, Grand Old House restaurant and Cayman Travel Services, Crighton’s bread and butter has always been real estate and development.  

He is managing director of Crighton Properties Ltd., the real estate company established by his father Rex in the 1960s. His father was also one of Cayman’s first developers, and over the years he and his father created several large subdivisions and residential communities, including Savannah Meadows, Savannah Acres, Beach Bay Heights, Beach Bay Glades, The Cays at Rum Pointe, Lalique Pointe and Crystal Harbour. 

Considering who his father is, Crighton said it was natural for him to get into real estate, but that he had to work to earn his spot in his father’s company. 

“My father had me working by the time I was seven… separating nails in his hardware store,” he said, referring to the Crewe Road Tile & Building Material shop that existed back in the 1970s. 

At 13, he started working in construction for his father, but jumped ship to work for Heber Arch. 

“Heber was offering 15 cents more,” he said, adding that his father was actually impressed by the move. “He wouldn’t give me a raise, so I went to work for Heber and that impressed him.” 

Crighton worked in construction until he was 16, when his father brought him into the real estate business. 

“But before that, I used to go in [to his father’s office] after school and sit and watch him and listen to him,” he said. 

Crighton said he learned about the real estate business from his father and his father’s friends, who included the late Jim Bodden, Cayman’s first National Hero. 

Even though he was learning a lot, Crighton said it wasn’t easy working for his father. 

“I don’t mind telling you, my old man rode me hard,” he said. “And that’s what you got to do. I didn’t appreciate it then, but I appreciate it now.” 

In 1997, his father stepped aside and let Crighton take the lead in the company businesses.  

“He said, “I guess I rode you enough; you’re broken now, so you deal with this…” 

His father is now 81 years old and in ill health, having suffered a stroke. Crighton still visits him regularly and speaks to him, even though he’s not sure his father understands. 

“He is the best man I ever knew. I mean, I still know him,” he said.  

“He never made a promise he couldn’t keep, and I can tell you he’s the only person in my life that has never, ever let me down. He never said… something that he didn’t do. That’s rare. I can’t say the same.” 

Like his father, Crighton said he thrives on stress. 

“I love it. It doesn’t bother me,” he said. “I just can’t take arguing. I hate arguing. I hate people getting pissed at me. I like to be friendly with everyone.” 

He said nothing good comes out of strife. 

“It’s so much easier to come to an agreeable resolution to something,” he said. “And I never burn a bridge. So many times I’ll say, ‘I’ll never touch this guy again or I’ll never do business with this person,’ and two years later, I end up having to do business with him or it’s a benefit for me to business with him, and I do it. I never say never.” 


Boom time  

Looking to the future, Crighton believes 2015 is going to be a “banner year” for real estate and development, building on what was already a good year in 2014.  

“In Lalique Pointe alone, there are 13 homes slated to be constructed in there in 2015,” he said. “And that’s just in one development. 

He said he has several things in the pipeline for 2015, as do many other developers. One of the projects he is working on with another prominent Cayman Islands developer promises to be “the end of luxury.” 

Crighton said that over the years, he has learned that a big key to selling property in the Cayman Islands is water. 

“It has to have water frontage,” he said. “If you don’t have water frontage, you’ve got to do something special. Whether you have canal, ocean front – you have to have water frontage. It’s a commodity that people buy, sell, and trade… and it’s scarcity that dictates that. It’s a small island, we’ve got the best beaches, we’ve got the facilities… and water plays a big part of it. People want to have that access to water. If you don’t have Seven Mile Beach, you have to have the North Sound.” 

Something else Crighton has learned over the years is the importance of the local and expatriate communities on real estate sales.  

“Back in the old days – in the ‘80s… you had to wait until tourist season because the tourists were buying everything,” he said.  

“The locals couldn’t afford to buy. Now, you have locals buying; they can afford to buy nice properties, expensive as anyone else. And then expats… never underestimate the amount of money expats spend in Cayman when it comes to real estate. I can remember when I was president of CIREBA, I was looking at an old letter I had written to [MLA] Kurt Tibbetts… and I was saying that expats had purchased… about 40 percent of the real estate bought in Cayman, and now I think it’s probably 50 percent.”  



Crighton is certainly an oenophile, although if you ask him, he’ll just tell you he just loves wine. Granted, he loves wine to the point that he owns enough to be able to open one bottle every day for about the next nine years and not run out, even if he didn’t buy another one. 

“I’ve got like 700 different wines,” he said. “Not 700 bottles; 700 different wines.” 

He first got into wines in his 20s, partially because his wife Sheila likes wine. 

He also came into possession of a lot of wine at one point in his 20s, the reason for which he didn’t want to divulge. 

“Let’s just say that something happened and I ended up with $700 or $800 worth of wine that I never ordered,” he said. “I ended up with a bunch of cases of wine. I started tasting it and I started reading about it, reading Wine Spectator, and it was very interesting – there’s a lot to it. That’s how I got into it.” 

Crighton has one of the best collections of wine on Grand Cayman, including many bottles of allocated wines that are very difficult to obtain.  

As much as he knows about wine, he’ll be the first to admit that there is plenty he doesn’t know.  

“No matter how good you think you are [at knowing about wines], you can always make a mistake,” he said. “It’s interesting when we do those blind tastings; you discover how much you really don’t know about wine and how much everyone else doesn’t know about it as well.” 

At a recent blind tasting gathering with other serious wine lovers, Crighton – who is well known for his pranks, especially when it comes to his good friend Gary Rutty – brought an old bottle of California Pinot Noir. 

“Everyone thought it was an absolutely fantastic Burgundy, but it was just one of those old Pinots that I had kicking around in the cellar,” he said with a laugh. 

Over the years, through events like the Cayman Cookout, Crighton has forged many relationships with wine lovers from all over, and he believes Cayman’s food and wine scene attracts the kind of high-end tourist Cayman wants. 

“I met some people, two couples, at the Cayman Cookout and they ended up buying condos here because they said, ‘we love it here.’ They said the food and the wine and the beaches are the best they had ever seen. 

Like most wine connoisseurs, Crighton goes through phases of which wines he prefers. He said he was on an “Italian kick” two years ago; last year was Spanish wines; and now it’s Bordeaux. He has an outstanding collection of California reds from boutique Napa Valley wineries, and even though California reds aren’t his favorite right now, he still likes them. 

“I still collect all of the Californias because once you get an allocation of something special, you have to buy it because there’s a waiting list of probably thousands of people trying to get your spot,” he said. “That’s the downside of it, because even in years that aren’t so good, you still have to buy it to keep on the allocation list. But the plus side is that California had been so consistent, just about every year since 2007.” 

Crighton said one of the reasons he collects wines is because they’re a good investment, noting that Grand Cru Bordeaux wines have increased in value between 1906 and 2007 by an average of 5.3 percent annually. He laughs, though, because he doesn’t actually sell many wines to reap any appreciation in value. But just as is the case with real estate, he’s always thinking about future value. 

“If I’m going to buy wine, I can’t help buying wine that I know will go up in value,” he said. “If I’m going to buy a cheap wine, I’m just going to buy it at a restaurant or something, but if I buy it [for home], I’m going to buy something that goes up in value, which means that I don’t really collect everyday stuff.” 

That fact can cause problems sometimes. When his daughter Ciara came home from college with some friends for spring break last year, she opened a $500 bottle of Scarecrow wine from Napa Valley. 

“I don’t even have an allocation of Scarecrow,” he said.  

“A buddy of mine got it and I got three bottles of Scarecrow ’08. She came home and it just happened to be sitting right next to the bar in the case stacked on a bunch of cases I had just gotten. It was the top one, so they pulled it out and opened one. And her friends had never had wine before in their life!” 

When he came home and realized what had happened, Crighton said he checked the bottle and saw that there was nothing left. 

“I said, ‘Look girls, everything you have left, pour into this glass, because there’s no way you’re going to drink this and I don’t get to try it,” he said with a laugh. 


Dale Crighton


Dale Crighton