Slice cabbage in half. Leaving core in, slice each half into evenly sized wedges. The cabbage will make approximately 10 wedges.
Wrap each cabbage wedge tightly with 1 to 2 pieces of bacon, securing with toothpicks.
Salt and pepper the wedges on both sides.
Preheat grill to 400 degrees (medium-high). Once heated, place bacon-wrapped cabbages on the grill, close the lid, and reduce heat to 250 degrees (low).
Check cabbage every few minutes, turning frequently to prevent burning.
Due to variances in grill size and type, the cooking time will vary greatly. The key to cooking this is not to get your grill to hot, turn frequently, and cook until the bacon is a nicely done and brown.
Remove from grill and serve immediately.
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