In 2009, jetBlue announced that it was looking for a new headquarters location, and was considering moving either within the New York City metropolitan area or to the Orlando, Florida area. In April 2009, Helen Marshall, the president of the Borough of Queens, said that the City of New York was trying to keep JetBlue in the city; in January 2010, the CEO of JetBlue, Dave Barger, and Governor of Florida Charlie Crist met in Tallahassee, Florida to discuss a possible move to Orlando. A decision was expected by March 2010, although a move would not happen until 2012, when its lease in the Forest Hills Tower expired.
In July 2016, jetBlue announced commercial flights from the United States to Cuba will commence in late August. On August 31, 2016, JetBlue Flight 387 from Fort Lauderdale–Hollywood International Airport to Abel Santamaría Airport, in Santa Clara, became the first scheduled commercial flight between the United States and Cuba in 55 years. Only charter flights were allowed under previous rules, which required that passengers had to arrive more than 4 hours before the scheduled departure and often endure long lines for documentation checks, late flight arrivals, and pay high baggage fees.
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For many years, analysts had predicted that jetBlue's growth rate would become unsustainable. Despite this, the airline continued to add planes and routes to the fleet at a brisk pace. In addition in 2006, the IAM (International Association of Machinists) attempted to unionize JetBlue's "ramp service workers", in a move that was described by JetBlue's COO Dave Barger as "pretty hypocritical", as the IAM opposed jetBlue's creation when it was founded as New Air in 1998. The union organizing petition was dismissed by the National Mediation Board because fewer than 35 percent of eligible employees supported an election.