Preheat oven to 350Lay a sheet of parchment paper on each of the two cookie sheets.
In a bowl, toss cut Brussels sprouts, olive oil, salt and pepper. Place the seasoned brussels sprouts on the prepared sheet pan, cut side down.
Lay the bacon slices on the second prepared sheet pan.
Place both sheet pans in the oven. Cook the bacon until brown but still soft enough to pierce with a toothpick, about 15 minutes. Cool.Roast the brussels sprouts about 20-25 minutes, until softened but still maintaining their bright color.
Cut the bacon into 1-inch square pieces. About 4 squares per strip
Cut the brie into ¼ inch thick slices, and then into squares, as close to uniformity as the bacon squares. The idea is to cut the bacon and cheese into sizes that fit between 2 ends of Brussels sprouts, leaving a little showing.
Assemble
Each skewers will get 2 slices of brussels sprouts, 2 squares of bacon, 1 cube of cheese and a dollop of onion jam. Place one end of the Brussels sprout on the toothpick, followed by a piece of bacon, then cheese, again with another square of bacon, a 1/4 teaspoon of onion jam, and finish with a second brussels sprout at the end. Place on a platter and sprinkle smoked chili flakes across.
Serve room temperature or pop in the oven for just one minute, but do not melt the cheese. These will store a day or two in the fridge.