It's a long way from Point Breeze to St. John in the U.S. Virgin Islands, and Terry McCoy didn't take a direct route.
Mr. McCoy, 65, grew up in Point Breeze and graduated from Central Catholic High School, but now lives on the Caribbean island where he produces hand painted clothing under the name of "Sloop Jones." His mother, Veronica MCoy, lives in Mt. Lebanon and his sister, Kathy, lives in Natrona Heights, so Mr. McCoy keeps strong ties to Pittsburgh.
"I was over winter and decided that if I was going to be poor, I wanted to live somewhere that I loved," he said of his move to the island that has fewer than 4,000 year-round residents.
Mr. McCoy started his trek south by moving north. After he graduated from Central Catholic in 1965, he went to Fordham University in New York City, where he earned a bachelor's degree in education. He also picked up his nickname, "Sloop," in college.
" 'Hang on Sloopy' was a popular song in 1964 sung by a group called the McCoys," he said.
"Someone just started calling me 'Sloop,' and it just stuck."
Mr. McCoy moved back to Point Breeze and coached track and cross-country at his alma mater, Central Catholic, before he decided to go to graduate school, heading north once again to Cambridge College in Massachusetts.
"At the time, it was the Institute for Open Education. I'm not really sure what I was planning on doing, but I received a master's in the philosophy in education," he said. The time he attended graduate school coincided with the beginning of video and closed-circuit TV usage, and Mr. McCoy quickly mastered those skills. The college hired him when he graduated.
"It was basically a college that trained teachers, so I would videotape teachers in class so the professors could use the tapes for training," he said.
In addition to his video work, Mr. McCoy also became interested in still photography and started his own photography business.
"It was fun, but it didn't pay the bills so I had to work as a car salesman to earn real money," he said. "And that was great training for an artist. It really helped me learn how to talk to a lot of people and how to sell something."
In the early 1980s, Mr. McCoy took a job selling English taxicabs for a company in Detroit. Since he was a traveling all over the eastern United States, Mr. McCoy lived in the Boston area. When that business failed, he joined a friend who was producing clothing in El Salvador.
"We had a contract to produce 500,000 turtlenecks. It was right after a civil war there and the factories had been sitting idle. We had 150 people working for us," he said.
And with his clothing business came an error that would change his life. When Mr. McCoy ended up with 300 unused T-shirts by mistake, he needed to do something with the shirts.
"It was the mid-1980s and the crafts movement was big and tie-dying was in a revival. I walked past this little store and thought the shirts looked like some of my watercolors so I got the idea to paint the shirts," Mr. McCoy said.
He painted six of the shirts and took them to the store, where they immediately sold out.
"I used the money to buy more paints and soon I had them all sold," he said. He bought out his clothing partner -- whose last name was Jones -- and Sloop Jones became not only the name of his business selling hand-painted clothing, but his official nickname.
As he traveled back and forth to El Salvador, Mr. McCoy realized he liked the warmer weather a whole lot better than winters in the north. Now with his wife, Barbara Alpren, the two started thinking about moving to a Caribbean island, particularly after vacationing in Tortola, a British island. Ms. Alpren, a physical therapist, also was ready for a change, so the two chose the small island of St. John since it was a U.S. territory.
In 1989, the couple settled into a small rented house on the east end of the 20-square-mile island.
"We would paint the clothing and hang it up to dry on a 60-foot clothes line outside of our shack. Tourists would drive past and stop," he said.
Sloop Jones moved from a small retail shop to a wholesaler in the 1990s, with three sales representatives selling the clothes across the United States.
The couple moved to a larger house and created a studio and retail store at the site.
"It was really a crazy time. We had five painters helping me paint and we were always working," Mr. McCoy said.
Over time, the business downsized to the current size with one retail store in Cruz Bay on the island carrying the line in addition to the main store and website. Mr. McCoy also owns Dish and DAt, a commercial satellite service.
Once again, Mr. McCoy is teaching. He recently started hosting workshops teaching visitors how to paint their own T-shirts.
"We've been hosting private workshops and thought we would open them to the public. It is a fun experience, and I enjoy teaching," he said.
Kathleen Ganster, freelance writer: email@example.com First Published April 11, 2013 8:45 AM