A friend is gone
Yankee Jack — A Friend Is Gone
A portrait of Yankee Jack was painted by Steven Heuel who painted all the murals in The Bull.
If you asked 100 people in Key West who was John Pittorino, no one would know. If you ask the same people, “Who is Yankee Jack?”, everyone will tell you he’s was the cool entertainer, musician at The Bull on Duval Street.
John Pittorino was better known as Yankee Jack. He was former high school football star in his hometown in Maine. He had two daughters, Elisha and Adrianne. He was a lobster fisherman and would supplement his income by singing during the off-season. Soon, he was a full-time musician, singer, and very cool songwriter.
Yankee Jack began his 40 plus year career entertaining as a country singer with a full band, opening for big name acts like Willie Nelson, Charlie Daniels, and countless other country legends. After a divorce, he moved from the Boston area in 1989 to Key West and never looked back.
He first started as a busker on Duval Street and then quickly became a pub entertainer at the Quay and most famously, for almost 30 years, at The Bull on the corner of Duval and Caroline Streets.
He published ten albums of very cool music with songs like “Same Sex Sunday”, “Manatee Woman”, “Very Conch-Troversial”, “Good Girls Go To Heaven (All the Rest Will Find Key West)”, and many, many, more.
Yankee Jack also wrote a Kindle book, “Was It Something I Sang”, which can be found online. He dedicated it to his second wife, Katherine saying “You cannot bullshit this woman”.
If you liked the former Yankee Hall of Famer Yogi-isms such as “Baseball is 90% mental. The other half is physical.” then you will love the comedic tropical-folkism of Yankee Jack, “…beauty is just a light switch away.”
Yankee would brag that he only worked 20 hours a week – five days of four hour shifts on the keyboard at the Bull on Duval Street. He is quoted as saying, “There is no substitute for life in Key West”. On that he would find almost unanimous agreement.
Another Yankee Jackism, “I enjoy being on stage. When I perform, it is as close to masturbation as one can get with his pants on” This and many other philosophical tidbits are in the first three pages of his book. Can you imagine what the rest of the book is like?
Famous artist Steven Heuel painted all the murals on the walls of the Bull and some of the Green Parrot. Yes, Jack coin it in a song “On the Walls of the Bull”. Steven also painted a very nice portrait of Yankee Jack with his wide brimmed hat looking back over his shoulder. It would have been his next album cover.
Yankee Jack’s oldest daughter Elisha was dating an Irish guy. With their traditional Italian upbringing, Jack said this was a bit of an “inter-racial relationship”. It inspired Jack to write a song “Gaelic and Garlic”, with lyrics “Gaelic and Garlic, like water and oil – they won’t come together until they start to boil”.
Yankee Jack took advantage of many opportunities to write music. He bragged he voted for Reagan and Bill Clinton and to the end never regretted either of his choices. He was as independent as one could get. He wrote a Bill Clinton song “Sex Between the Bushes” (Bush I & 2). Not to be too politically incorrect, he also wrote “Jesus Was A Democrat” in which he asks god for a sign to guide us along “Send someone that we can trust. Send a woman. Send a man. But don’t send a Republican.” It was on his last album, Conch-Troversial.
He loved to write music that put people in their place. He specifically lamented the “Barbie Dolls” that would come into the Bull with perfect hair and 45 minutes of makeup. They tend to look down on less attractive women. 
He wrote this song just for them “Beauty’s Just a Light Switch Away” with lyrics like – “Pretty women they like to dine – Ugly girls can cook just fine – And beauty is just a light switch away”.
Yankee Jack was a big man, well over 300 pounds. Key West Lou, his good friend and weekly golfing buddy. They would meet every Wednesday morning for nearly 20 years to play golf. Lou said he was a great golfer who could drive the ball a country mile. Yankee Jack would periodically diet, knock off 70 pounds, and then give up and start eating again.
On March 14, 2016, Yankee Jack, arriving at the Bull for his music shift, he suddenly collapsed and died. When Key West Lou discovered his good friend had suddenly passed away, he was deeply saddened. He penned his next column about his love for Yankee Jack and ended with “I liked Yankee. Everyone liked Yankee. A friend is gone.”
Yankee Jack once said, in song of course, “Jimmy Buffett wasn’t wrong. I read his books and I sang his songs. He led me to where I belong. It’s a permanent vacation. Key West I’m here for the Duration.”
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