In a small saucepot, simmer the sugar in 1 cup of water until dissolved, about 3-4 minutes. Remove from heat and drop in the tea bags. Steep 10-12 minutes. Squeeze excess syrup from the used tea bags back into the pot and discard the bags.
In a cocktail glass, combine the bourbon, orange juice, 1/2 oz chai syrup (or more to taste), pumpkin puree, and bitters. Stir to combine. Fill the glass with ice and stir again, then top with sparkling water and garnish with fresh mint and a star anise, as desired.
Notes
*To store syrup: Unused syrup can be stored in the fridge, sealed, for up to 2 weeks.