- 1 orange wedge, unpeeled
- 1 raw sugar cube
- 7 dashes Angostura bitters
- 7 dashes orange bitters, preferably Regan’s
- 2.5 ounces 107-proof bourbon, preferably Pappy Van Winkle
- Ice cube or sphere
- Trim the tips off the ends of the orange wedge to cut down some of the bitterness and place the wedge in a large cocktail shaker. Cover the shaker with a bar napkin. Put the sugar cube in the center of the napkin and carefully coat the sugar cube with the bitters; the napkin will catch the runoff. Drop the soaked cube into the shaker and discard the napkin.
- Using a bar spoon or a muddler, muddle the sugar with the flesh of the orange wedge; be careful not to push into the pith, as that would make the cocktail bitter. The result should be a thick syrup. Add 1 ounce of the bourbon and muddle for 3 minutes. Add a big ice cube or sphere. Add another ounce of bourbon and stir for 30 seconds. Pour into a rocks glass.
- Top off with the remaining 1/2 ounce of bourbon and stir for 5 seconds. Serve immediately.