Ok, I respect the attempt to create something worthy of the classic rap song. But this misses the mark in my humble opinion. Gin and Juice should be well, Gin and (Orange) Juice. So we start from a base of equal parts London Dry Gin and fresh-squeezed Orange Juice. Served over a king-size ice cube in an Old Fashioned glass, with ample time for melting and dilution to work their alchemy. Not bad, good even. But how to take it to the next level without compromising its fundamental nature? Not by adding grapefruit juice. Nope. In my opinion, just a dash or four of Luxardo Maraschino (to taste) makes this something that even Snoop D-O-double-G would approve of.
Ah yes, the "muddled fruit" vs. I guess, "minimalist" Old Fashioned debate. Aside from Mr. Difford here, I learned about the most about cocktails from the legendary Dale DeGroff and the OG cocktail historian Ted Haigh. Haigh refers to the muddled fruit version as a "ugly slurry". Yet no less of an authority than DeGroff is apparently on Team Ugly Slurry. DeGroff, in the first edition of Craft of the Cocktail: "Those other guys just want some sweetened whiskey, not an Old Fashioned." It's summer here in Cali, and I just a muddled fruit Old Fashioned with blackberries, an orange slice, and some beautiful farmer's market apricots. So let's split the difference! When all those things are in season, muddled fruit is the way to go. Once the chill of winter comes in, I'm sipping on some sweetened Bourbon. (Of course, it's not just sweetened Bourbon, it's sweetened Bourbon plus Angostura bitters and an orange twist.
This is one cocktail where the history is probably more interesting than the drink itself. It's presented here as a variant of the Long Island Iced Tea, but I think this is a case of convergent evolution. My theory is that this originated among American servicemen in the Philipines, late 1940s to early 1950s. That would explain the Spanish and the proto-Fratboy aspects of it. But I have no evidence. Would love to know the first published source of this cocktail.