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Heat the olive oil over medium heat. Add the shallots and stir occasionally for 5-10 minutes until very soft and fragrant.
Add the grapes and turn the heat up to get everything hot. Pour in the bourbon, vinegar, and wine – it should sizzle a little bit to get the browned bits off the bottom of the pan. Add the cinnamon stick and bay leaf. Simmer, stirring occasionally, for about 30 minutes or until the grapes have started breaking down.
Smash the grapes into a jam-like consistency using the back of a wooden spoon. Remove from heat, cool, and serve on cracker with cheese (Manchego cheese and goat cheese are my favorite with this).