The answer to my first question, “How long were you in the Army,” told me pretty much all that I needed to know about the man. David “Bat” Masterson, had at first replied “38 years,” then, with a subtle change in his demeanor, restated his answer, “38 ‘great’ years.” Beginning in 1972, Bat had flown the Huey U-1 Iroquois, AH-1 Cobra, OH-58 Scout and the UH-60 Blackhawk, attaining the highest of all warrant officer designations, Chief Warrant Officer 5. In addition to being a pilot, he was an instructor, test pilot, and an aviation safety officer. Pilots who had been his students often returned, thanking him for sharing his expertise. After his initial US Army enlistment, Bat remained in the service, spending time in the Army Reserve Command and the Illinois Army National Guard. Then, as he explained to me, by “Order of the Secretary of the Army,” in 2004, he was returned to active duty, initially serving in Iraq, then Germany. With that requirement completed, he returned to what the Army calls IRR, Individual Ready Reserve, when, once again, in 2009, the Army had other plans for him. In 2009, at the age of 56, much to the dismay of his wife, the Army had a role requiring a CW5, calling him back to active duty in Iraq. Coming home, he retired from military service. During our chat, there was something about him that I couldn’t put a finger on, until he told me why he was in Key West. For nine years, he has been a contestant at Sloppy Joe’s Bar in their annual Ernest Hemingway look-alike contest, to the benefit of the College of the Florida Keys, winning the competition in 2024.