Lots of insider information to understand this one. Thanks for the enlightenment...
The Pusser's distributor from Key Largo showed up at the San Francisco YC in his touring van, several weeks ago, for the Melges 24 Worlds. He camped out next to the Coral Reef Sailing Gear tent and discretely served up all levels of Painkillers to interested parties. Needless to say, I was quite interested.
Turns out we'd met him in Key Largo at a Melges 24 regatta in 2007. Somehow those memories were rather fuzzy.
A comparable libation, which seems to be popular in New England, and which I first encountered at Block Island Race Week in 2011, is the Frozen Mudslide.
Frozen Mudslide Recipe - Allrecipes.com
Needless to say, this is a summer beverage, not suitable for winter consumption (particularly after a day of Laser frostbiting).
It's interesting how different drinks are associated with yacht racing. In San Francisco, SFYC is noted for its lethal Mai-Tai, while the St. Francis YC is celebrated for its Dark-and-Stormy (though I sailed with one skipper who liked to buy the crew a Ramos Fizz at St. Francis YC before heading out on the water to race). Needless to say, Mt. Gay Rum shows up at most regattas, and Mt. Gay-and-tonic (w/ lime) is my preferred regatta drink. I've paid for all those red caps many times over.