Wow this looks good, I love whiskey & pineapple juice.
3/4 oz. Rittenhouse bottled in bond rye (or other 100-proof rye).
3/4 oz. Jamaican rum.
3/4 oz. Campari.
1/2 oz. fresh lime juice.
1/2 oz. demerara syrup.
2 oz. pineapple juice.
Campari was my no 1 hated alcohol until I had a Jungle Bird (accidentally with lemon instead of lime; that version has since become my favorite drink, period). In the Jungle Bird, it was not just good, it was great. Had a couple of those over a couple of months. Learned to love Campari. Negroni is now another favorite, and tbh I wouldn't mind if someone handed me a glass neat.