Start by getting your braising liquid ready. Fill a large stock pot with enough cold water to fully submerge your octopus, about 4 to 5 quarts. Add the white wine, quartered onion, half the lemon (squeezed in then dropped in), 3 smashed garlic cloves, kosher salt, whole peppercorns, 1 rosemary sprig, and 2 thyme sprigs. Bring the whole pot up to a rolling boil over high heat.

Once the braising liquid is boiling, carefully lower the octopus in using tongs. Here is a classic pitmaster trick adapted from Mediterranean tradition: dip the octopus in and out of the boiling water three times before fully submerging it. This causes the tentacles to curl up tight and beautifully, which gives you those perfect grill-ready arms. Once fully submerged, reduce the heat to a gentle simmer at about 190 to 200 degrees Fahrenheit.

Simmer the octopus low and slow for 45 to 60 minutes depending on size. A 3-pound octopus will need the full 60 minutes. You are looking for fork-tender flesh that offers almost no resistance when poked with a skewer or paring knife. Do not rush this stage. Just like a long brisket cook, this is where the collagen breaks down and transforms tough muscle into silky, tender meat. Check at the 45-minute mark by piercing the thickest part of the head.

While the octopus braises, fire up the grill. You want a two-zone setup with a massive pile of lit lump charcoal on one side creating a direct heat zone that reaches 500 to 550 degrees Fahrenheit at the grate. Let the grill preheat with the lid down for at least 15 minutes. While it heats, mix your herb baste: combine the remaining 3 tablespoons of olive oil, 3 smashed garlic cloves (minced fine), chopped rosemary, stripped thyme leaves, smoked paprika, and red pepper flakes in a small bowl. Set aside.

When the octopus is done braising, remove it from the pot and let it rest and drain on a wire rack or cutting board for 5 to 10 minutes. Pat the exterior lightly dry with paper towels. Moisture is the enemy of a good char. If the octopus has a large head, you can optionally cut it in half to create more surface area for grilling. Separate the tentacle cluster if it makes it easier to manage on the grate.

Brush the octopus generously with the herb baste, making sure to get into all the nooks and crannies of those tentacles. Hit the hot grill grates with a quick brush to clean them, then lay the octopus directly over the hot coals. You should hear a serious sizzle the moment it touches down. That sound means you are building bark and char. Do not move it for the first 2 minutes.

Grill the octopus over direct high heat for 2 to 3 minutes per side, turning with your long tongs. You are looking for deep grill marks, a lightly crisped and charred exterior on the tentacle tips, and a gorgeous caramelized color all over. Baste with the herb oil each time you flip. The total grill time should be 6 to 8 minutes. Do not over-grill: you already cooked it through in the braise, so this stage is purely about texture, char, and flavor layering.

Pull the octopus off the grill and let it rest for 5 minutes on a cutting board. Do not skip this rest. Just like you rest a steak or a pork shoulder, resting lets the juices settle back into the meat. After resting, slice the tentacles into 2-inch to 3-inch segments using a sharp knife, and cut the head into strips or chunks. Arrange on a serving platter.

Finish the dish with a squeeze of fresh lemon over the top, a drizzle of your best olive oil, a sprinkle of flaky sea salt, the splash of red wine vinegar, and a generous shower of chopped fresh parsley. If you want to grill the lemon half cut-side down over the coals for 2 minutes before squeezing, do it. Charred lemon juice is an absolute game changer that adds a smoky-tart brightness you cannot get any other way. Serve immediately while still hot.