John started playing trumpet at age 5 because his dad was a trumpet player. He joined his school band, went to college, dropped out, and then got his first major musician job with the Tommy Dorsey orchestra. He later did a stint with the O'Jays and ended up touring with them. He eventually moved to Miami and attended the University of Miami School of Music where he played in the concert jazz band. He started working in a club called Bananas, where he had the opportunity to play with artists such as Tony Bennett, Dianne Carroll, Bob Hope, and Ben E. King.
John won the Downbeat Magazine student-recording award for Outstanding Performance by a Jazz Instrumentalist in 1982. He spent time during the "fabulous 80s" at jazz radio WDNA in Miami; however, in 1987 he was a "starving musician" paying bills as a substitute teacher in the Dade County public schools.
In 1992, John was selling stereos, working at a local Circuit City store and "wasn't getting anywhere." Then he got a call from a friend who was in the studio with Jimmy Buffett, where they were looking for a trumpet player. He sent a tape, resume and picture and two weeks later he got the job.
John has always been a jazz player and, when he's not touring with Jimmy Buffett, he can be found playing with a local swing band in the Palm Beach area.