Rinse the octopus under cold running water.
Place onion, garlic, bay leaf, paprika, salt, and 2 tablespoon olive oil into a large pot or large saucepan that will fit all of your octopus. Cook and stir over medium heat until onions start to soften, about 5 minutes.
Add the wine, vinegar and peppercorns to create the braising cooking liquid. Bring to a simmer.
Transfer octopus into braising liquid, turning to coat with the liquid. Cover; reduce to low heat. Simmer 20 minutes and turn octopus over. Continue cooking until octopus is knife-tender, another 40 minutes.
Remove octopus from pan and cut the octopus tentacles in to pieces with a sharp knife (whatever size you prefer).
Whisk the marinade ingredients in a medium bowl. Add the octopus to the marinade bowl and gently roll to coat.
Preheat the grill or stovetop pan.
Set the grill to medium-high heat and coat the grates with oil. Set the octopus directly onto the grates or pan. Let the outside brown for 2-3 minutes per side. Rotate to develop a char then place onto a platter with extra marinade.