Season all sides of the roast with salt and pepper. Add two tablespoons oil to a heavy Dutch oven or other pot that has a tight lid and heat over medium-high heat. Add the roast and sear on all sides until browned, adding the additional olive oil as needed.
When the roast is turned, add the onion and cook for several minutes right alongside the roast, stirring now and then, then when the roast has browned nicely, add the garlic and cook till fragrant, about a minute. Mix together the tomatoes, chipotle chili, cayenne, and ground cumin and dump it over the roast. Add enough water (go down the side of the pan so you don’t wash the vegetables and spices off the meat) to nearly come to the top of the roast. Bring to a boil, reduce to a low simmer and cover tightly.
Continue to simmer very slowly for three to three and a half hours, checking the liquid level towards the end so the sauce (which should be nicely reduced) does not dry out, until the roast is fork-tender. Let the meat cool a bit and gently break it into chunks and return to the sauce.
Keywords: Bargain Meal of the Week, Beef, canned tomatoes, Chipotle, Chuck Roast, Freezes Well, Mexican or Southwestern, Mexican Pot Roast, Pot Roast, Rotel