Prepare Calamari: 

1. Rinse the calamari. Run water through the tube and drain it. Pat dry with paper towels.
2. With a sharp knife, chop off the tentacles, finely chop them, and place them in a bowl. 

Make Filling: 

1. Heat olive oil in a large frying pan with medium-high heat and add the minced garlic. When the garlic is just beginning to give off its aroma (1-2 minutes), add the tentacles and stir. Add wine and let simmer for a few minutes—season with salt and pepper. Then, take off the heat and let it cool. 
2. Add the bread, egg, cheese, and parsley to a medium mixing bowl and stir to combine. 
3. When the tentacles are completely cooled, add to the bread crumb mixture and stir to combine. 

Stuff Calamari:

1. Use your fingers, a pastry bag with a broad tip, or a small spoon to stuff the calamari with the filling.
2. Be sure to press down to fill the bottom end of the calamari. Leave about an inch of space at the top since the filling will expand while cooking and may come out of the top. Secure the open end with a toothpick. Cover with plastic wrap and set aside.

Prepare Sauce and Cook Stuffed Calamari: 

1. In a large saute pan with medium-high heat (large pan enough to fit all the squid in one layer), sauté a garlic clove and red pepper flakes in olive oil. When it is just beginning to brown, remove it.
   Add the stuffed squid and turn them in the oil until they turn an opaque white (about 1 minute on each side). 
2. Add the tomato puree and salt, stir to mix it thoroughly into the cooking juices, and cover. Lower the heat. Let the squid braise in a slow simmer until tender, about 30 minutes (or longer if your squid is very large).
3. Transfer to a serving platter and serve warm with crusty bread! Don’t forget to remove the toothpicks.