1 5-lb. boneless, skinless pork shoulder, cut into 1- to 2-inch pieces
10-ft. hog casings*
¼ cup dried oregano
¼ cup fennel seeds
3 Tbsp. kosher salt
2 Tbsp. dried basil
2 Tbsp. sugar
1 Tbsp. freshly ground black pepper
1 tsp. cayenne pepper
1 tsp. red pepper flakes, plus more to taste
2 Tbsp. grated garlic
3 Tbsp. dry red wine
Freeze all grinder parts, including the die, until very cold, about 1 hour. Refrigerate a large stainless-steel bowl until cold.
Line 2 baking sheets with plastic wrap. Place the pork in single layers on the baking sheets, cover with more plastic wrap and freeze until the meat is very firm but not frozen, about 1 hour.
Meanwhile, soak the hog casings in lukewarm water at least 30 minutes. Rinse and set aside.
In a small bowl, combine the oregano, fennel seeds, salt, basil, sugar, black pepper, cayenne and red pepper flakes; set aside.
Remove 1 baking sheet of pork. With the mixer on high speed, grind the pork 3 to 4 pieces at a time, collecting the ground meat in the chilled bowl. Repeat with the remaining sheet of pork.
Add the garlic to the ground meat and use your hands to gently mix and distribute the garlic, about 20 seconds. Sprinkle the reserved spice mixture evenly over the pork and knead, rotating the bowl, until the spice mixture is evenly distributed and a light film has formed on the bowl, about 1 minute.
Add the wine and knead until the mixture holds together and is very stiff (it will spring back when pressed), about 1 minute. Form ¼ cup mixture into a 3-inch patty, press it onto your palm, then flip your hand over. If it sticks at least 5 seconds, its ready. If not, continue to knead in 15-second intervals, trying again until it does. Dont over mix, or the sausage will be crumbly.
Remove the meat grinder attachment and replace with the sausage stuffer attachment. Slide the casing onto the nozzle, leaving 6 inches hanging loose from the end.
Working with a partner, pack a handful of meat into the top of the stuffer. With the mixer on high speed, use the plunger to push the meat through, firmly filling the casing and sliding the filled sausage onto a baking sheet. As the casing fills, lightly prick any air bubbles with a sausage pricker or pin. Stop filling when 6 inches of empty casing remains.
Tie off the starting end of the casing, knotting it flush with the meat. Measure 6 inches from the knot and pinch. Twist the link toward you 2 rotations. Repeat and twist 2 times in the opposite direction. Continue measuring and alternating the direction of the twists until you can no longer make another sausage. Squeeze out the extra meat and tie off the casing. Use scissors to cut the sausages at the twists into links.
Prick each sausage link in 3 places with the sausage pricker or pin to prevent bursting during cooking. Arrange the links on a parchment-lined baking sheet and refrigerate, uncovered, to dry casings, at least 12 hours.
Sausages will keep refrigerated in an airtight container 3 to 4 days or frozen up to 6 months.
* Hog casings are available at The Block Restaurant and Butcher and Wenneman Meat Co. Call ahead to confirm availability.