The name Major Bailey goes back to Victor "Trader Vic" Bergeron's 1947 Bartender's Guide, where the original — gin, mint, and citrus, built like a julep — is a documented, real Trader Vic creation. Major Bailey No. 2 is a distinct, separately-numbered riff that swaps gin for rum and adds pineapple juice and triple sec, charging the drink into full tiki territory. Difford's Guide is the only place this site could find the No. 2 recipe published, and its own page states plainly that no creator or origin story is given for this specific variant — so treat the numbering as a naming convention connecting it to the real 1947 drink, not as evidence this exact rum version has the same pedigree.
A rum-based Major Bailey charged with a full shot of pineapple juice and triple sec — dangerously drinkable.
Two Drinks, One Name
Trader Vic's original Major Bailey is a gin-based mint julep relative — muddled mint, gin, lemon and lime, sugar, built over crushed ice. It's genuinely documented in his 1947 guide and sits closer to a South Side than to tiki. This No. 2 keeps the mint and the crushed-ice service but rebuilds everything else around rum, pineapple juice, and triple sec, landing much closer to a Mai Tai relative than a julep.
Nothing on Difford's page claims a specific bartender or date for the No. 2 version, and this site found no independent source for one. It reads like a modern variant built on the strength of the original name rather than a separately-attested vintage recipe.
The Spec
Muddled mint at the base, a full two ounces of rum, a real pour of triple sec and pineapple juice, and a small citrus-and-syrup adjustment to keep the sweetness in check.
Muddle gently, don't pulverize
The mint leaves get bruised in the shaker base before the liquids go in — enough to release oil, not so much that the drink turns bitter and grassy. A dozen leaves sounds like a lot; it's calibrated for a full two-ounce rum pour and a tall crushed-ice serve.
Lemon and lime, not just one
Splitting the citrus between lemon and lime rather than doubling up on one gives a rounder acid profile against the sweeter pineapple-and-triple-sec pairing — a small move, but it keeps the drink from tasting one-note.
Bottom Line
A strong, easy-drinking rum-and-pineapple cooler that borrows a famous name without fully earning its provenance — good on its own terms, but don't confuse it for the 1947 original.