The Original “Hold My Beer” Story

Big Jim likes to use the phase "hold my beer."

In short, it means you're going to prove someone wrong and you're going to need both hands. (Millennials would translate it to mean "bet".)

But where did this saying begin? Big Jim seems to think it was in 1950's New York City...

Thomas Fitzpatrick was drunk and decided to steal an aircraft not once, but twice and wound up landing it in the middle of Manhattan - all on a bet.

Fitzpatrick drunkenly flew and landed the airplane in the middle of the street in front of a bar. He had stolen the aircraft from  a nearby school of aeronautics.

When police watched him land, they were in awe...and then they arrested him. He was later fined $100 (equivalent to $800 today) but was released soon after. There was no damage to the airplane, so the owner chose not to press charges, in fact, he was kind of amused by the stunt.

And then there was that second time...  The first instance was somewhat of a success story, but the second did not end so well..

A couple years later, Fitzpatrick was telling his story, only to be challenged. No one believed such a tall tale, so, naturally, Fitzpatrick [probably] said "Hold my beer.."  and set out to prove them wrong.

Fitzpatrick once again stole a plane from the same school of aeronautics as before and flew that plane threw New York City in the dead of night...and he pulled it off. He flew the plane and landed it without crashing. Only this time, he didn't get off so easy...

A judge sentenced Fitzpatrick to six months in jail and said “Had you been properly jolted then, it’s possible this would not have occurred a second time.”