Songfacts®:

• This calypso classic is a highly political song, with Trinidad and Tobago the "sinking ship." Gypsy is Winston Peters, a calypso artist who was active in politics. He wrote the song on behalf of the National Alliance for Reconstruction (NAR), a new party that was running against the People's National Movement (PNM), which had been in power for 30 years, most of it under the leadership of Eric Williams, who died in 1981, replaced by George Chambers. In the song, Gypsy names names:
  
  The Trinidad, a luxury liner, sailing the Caribbean Sea
  With an old captain named Eric Williams
  For years sail smooth and free
  But sadly Eric Williams passed away
  The ship hit rough water that day
  Someone turn the bridge over
  To a captain named Chambers
  
  The NAR won the elections but lost their majority in 1991. In 2000, Peters was elected to Parliament.
• Gypsy is also known for his songs "Rhythm of the Nation" and "Little Black Boy." The name Gypsy was assigned to him by his grandparents because he was always moving around.
• The song deals with a specific country during a specific era of politics, but it has endured and found an audience far outside of Trinidad and Tobago, as many people view their countries as sinking ships with politicians to blame.
• In 2020, David Johansen, known as the frontman for the New York Dolls, reworked this song ahead of the United States election between Donald Trump and Joe Biden. In his version, the lyrics are essentially the same, but with the references changed. "I've always liked the song," he said in a Songfacts interview. "I played it on my radio show on Sirius, and I thought I should sing this song and make it about the US."
  
  "A lot of people make songs that are dire and dismal about the situation," he added. "You're bombarded with that kind of stuff on the news all the time. This one sneaks the message in there with a happy song."
  
  Johansen got his wish when Biden defeated Trump.