Remove the stems from the broccoli rabe. Shake and rinse the broccoli rabe in colander to remove the excess liquid, but the rabe doesn't have to be thoroughly dry.
Heat a large pot over high heat until very hot. Add the olive oil. When the oil is almost smoking, add the garlic and cook for a few seconds until it is light brown. Add a couple of handfuls of rabe and toss with tongs, incorporating the garlic so it doesn't burn on the bottom of the pan.
Add the remaining rabe all at once, or in batches if your pot isn't large enough to hold it all at once. Toss constantly so the rabe wilts evenly. When the rabe is cooked, season with salt and pepper. Continue cooking over high heat, tossing often until the excess liquid evaporates.
Turn the rabe out into a bowl and let it cool to room temperature, then season with wine vinegar. Eat at room temperature or refrigerate up to 2 days and eat cold.