Goodbye Mr. Bartender: Another Cayman rollover casualty

Stephen Bebber left Grand Cayman on Saturday, 2 August, probably for the last time.

Mr Bebber came to Cayman seven years ago thanks to a lucky break. But his luck ran out a year ago, when he received official notice from Government saying that his most recent work permit would be his last.

Everyone knows about the official Cayman Islands Government policy whereby non-Caymanian residents are not permitted to remain here longer than seven years. To the average Caymanian, the so-called ‘rollover’ policy seems to be a hazy concept.

To the many thousands of long-term expatriates who have happily made their home here for years, however, the rollover is a very real and very painful experience, draining both emotionally and financially.

Stephen Bebber’s first taste of life in the Caribbean came while working for a month in the Turks & Caicos. But that brief sip convinced him that he wanted more.

Returning to his Toronto home with itchy feet, he moved cross-country to Vancouver, where he took up a job as a bartender at an upscale restaurant. It was while working in Vancouver that he first heard about Cayman.

“There was a recruiter doing large-scale open-session interviews for bartending jobs in three different Caribbean locations. About a thousand people showed up for what was really only a handful of jobs,” he said.

The recruitment manager liked Mr Bebber’s personality, and the fact that he already had experience bartending in a top-tier eatery didn’t hurt.

Soon enough, he kissed the brutal Canadian winters goodbye and was serving drinks at La Bodega just off Seven Mile Beach.

Though neither the salary nor the tips were very good, for the next two years Mr Bebber, now 30, began to settle into Cayman life. And his Cayman luck continued when the food and beverage manager at the Hyatt offered him a job working at that hotel’s Bamboo restaurant.

Bartending at Bamboo not only meant a better salary and bigger tips, but also more importantly he was now regularly meeting the local elite, from top government leaders and business gurus to corporate high-flyers.

Chatting with these people convinced him that tending bar might be fun for a while but not long term. Enrolling at the University College of the Cayman Islands, he decided to sign up for full-time courses (“I wanted to catch up for lost time”) with the aim of earning a degree in economics.

“I’d work at Bamboo from 4:00 pm till 2:00 am, and then be up in time for my classes which began at 8:00 am, and ran till 2:30 pm. I’d have like a nine-minute nap at home before heading out to work,” he recalled.

Eventually he earned his associate degree and was steadily building more credits towards a bachelor’s degree. Then the “rollover letter” arrived.

“Two years ago, I first began to think about the rollover. But, I kind of put it out of mind. I thought: ‘Why would I want to leave this island, where all of my best friends are?’ But now they’re all gone. One, by one, by one, they’ve all had to leave the island - to the US, to Canada, to Nicaragua….

“I can appreciate that this is a small island, and the Caymanians don’t want to be dominated by expats. But people like me are not asking to vote. We’re not asking to run the country, only to make a home here.

Franz Manderson,
Chief Immigration Officer

“Several years ago I wanted to buy a house. I wanted to invest locally as well, and I had been putting my money in the local economy all along, not just hoarding it as some people do. I’ve always felt as if I were an ambassador for Cayman for every visitor I’ve met, whether while working or not. I’ve even flown my parents here several times for holidays.

“But now, because of the rollover, instead of investing my hard-earned savings here - this island that is kicking me out - I now have no choice but to take it back with me to Canada.”

Mr Bebber was on-island for Hurricane Ivan and endured its full fury. “Basically I lost all of my stuff. The water was over the roof of my car. And almost all my household things were destroyed.”

Though he took the loss from the storm in stride, Mr Bebber still feels wounded by the fact that those expats who left the island for a year - waiting for things to be cleaned up - were rewarded with a new additional seven-year permit when they came back.

“Whereas I stayed here, and helped rebuild the country, helped the Caymanians clean things up, to bring the country back. But I feel like I was punished for having stayed.

“The government says you can go away and come back in a year and try to return. But how can a person put their entire life on hold for a year, based on the fact that they might let you return, and that if they did, you might be able to find another job here?”

But Mr Bebber has accepted his fate. “I’ve been dealing with this for a while now, and I’m ready to move on. I’ve put seven years of my life here, and I really enjoyed living here and I think I’ve been contributing.”

He now plans to finish school in Canada and then go into the financial industry. “A lot of people ask me if I would come back to Cayman. I’d have to think about it long and hard. I mean - do you really want to consider making a home in a place that really doesn’t actually seem to want you?”