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The Toss That Launched North Salem Native's Military Career

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Capt. Craig Massello Credits: Photo courtesy of Augie Massello
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NORTH SALEM, N.Y.--Described by loved ones as decisive and confident, Craig Massello appeared to contradict those characteristics when he left the direction of his military career up to a coin toss at the end of flight school in the late 1990s.

Looking back, the North Salem native said he actually was confident in either option: one side nudged him to fly fixed-wing planes and the other beckoned him toward choppers. But it was neither a move grounded in indecision nor evidence of a lack of self-assurance. It was an order from his captain, who said it would be the fairest way for him and another student to decide where they went, as they were equally qualified to do both. And although he admits he’s thought about that other Craig, he is pleased with the course of his career.

“In the end I’ve been able to fly the four main Coast Guard airframes,” he said. “So looking back at the coin toss, that was my start, but at the end of the day I still get to experience both sides anyway.”  

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In light of his recent promotion from commanding officer to captain, Massello, 43, and his family have relocated from Houston to Montgomery, Ala., to the Maxwell Air Force Base. He took a break from moving boxes to look back on his long career.

He has had his share of adventures, from braving swarms of media during the search for John F. Kennedy Jr. when his plane disappeared in July of 1999 to flying through the eye of Hurricane Katrina in 2005 to rescue three fishermen off the coast of Key West, Fla.
 

Massello graduated from Kennedy Catholic High School in Somers in 1991 and said he remembers his time there fondly. His passion for hockey developed when he was in high school, and he continues to play when he’s off duty. He said he hasn’t found an ice rink yet in Alabama, but is hopeful. Having flown commercially just once as a kid, he didn’t consider a military career until he was well into his high school years. He briefly entertained the idea of becoming a dentist during that time, but hasn’t thought of it since. Massello’s father, Augie, on the other hand might tell you his fidelity sometimes strays after a particularly dangerous mission, such as the Katrina case.

“I’m glad I heard about that one the day after,”Augie said. 

Other than what he called a natural parental concern, Augie said he is incredibly proud of his son’s accomplishments, which include the Naval Helicopters Association’s Aircrewman of the Year award for the rescue of those three fishermen.

“You’re always concerned about your kids, there’s no doubt about it, but the pride is unbelievable,” Augie said.
 

Massello, who had flown commercially once in his life before going to the Coast Guard Academy, was introduced to the idea by his late uncle, who lived near the academy in New London, Conn. The three of them went on a tour of the campus.

“Just at the time, they had one of the [helicopters] on the lawn,” Augie said. “My son said, ‘Ya know, dad, I want to fly one of those’ and that was it.”

Following the academy he served as deck watch officer aboard the USCGC Gentian and then went on to complete naval flight training in Pensacola, Fla. In July 1998, Massello was assigned to Air Station Cape Cod in Massachusettes. In 2012, he was the aeronautical engineering officer, leading a team of 368 that supported the crafts involved in the Coast Guard’s Joint Interagency Task Force South and Operation Bahamas, Turks and Caicos to counter drug missions, in Clearwater, Fla. 
 

Massello has held pilot designations in the MH-65D, HH-60J and HC-144A aircraft and holds a commercial FAA Airline Transport Pilot certificate. He also holds a masters in industrial engineering and business administration from the University of Pittsburgh. 
 

Massello said he is content with the variety of opportunities and jobs the Coast Guard has enabled him to pursue.

Now with his wife, Sara, and two children, Haeley, 9, and Conner, 6, to consider, he said he has begun to think about his future in the military.

“They’re still at a young age where moving is exciting but eventually we’ll settle down,” he said. 

Regardless, the “train for the worst-case scenario” instilled in him by a career in the military has only nurtured the confidence he has in that one fateful coin toss all those years ago. He said he is sure he’ll be content with whatever side of the coin he faces. 

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