Heat oven to 375ºF.
Place a roasting pan on the stovetop over a couple of burners and heat up about 1/2 cup of EVOO, a shallow layer, over medium-high heat. When oil is hot, add in potatoes, season liberally with salt and pepper, and cook till golden brown on cut sides, about 10 minutes. Add the garlic, chilies, oregano and bay to the browned potatoes, and cook for about 3-4 minutes more, turning occasionally. Transfer potatoes out of pan and heat up remaining 1/4 cup oil.