Wrap each olive with a piece of bacon and secure with a toothpick.
Preheat a grill for medium heat. When hot, lightly oil the grate.
Grill the olives until the bacon has crisped, about 10 minutes. Turn frequently and keep a spray bottle handy in case of flare-ups from the bacon grease. Remove to a paper towel lined plate to absorb any excess grease.