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Yankee Chili from Bob

An amazing pot of chili

Yankee Chili from Bob

Recipe by Toby Alan Dion Course: Food, Recipe, SoupsCuisine: SoupsDifficulty: Easy


Prep time


Cooking time


Total time






  • 5 LB bottom round roast

  • 2 can plum tomatoes (35 oz cans)

  • 2 medium onions

  • 1 bell pepper

  • 2 stalks celery

  • 7 cloves of garlic

  • 3 Tbs ancho powder

  • 1 Tbs chipotle powder

  • 3 Tbs cumin

  • 1 Tbs salt

  • 1 Tbs black pepper

  • 1 Tbs mexican oregano

  • Olive Oil as needed


  • Carve the roast across the grain into ½” thick slabs, and then further into ½” strips. Set these aside and prep the rest of the vegetables. Rough dice the vegetables and place in a bowl.
  • Prepare a stewpot (6 qt+) over low heat with a little olive oil and all the spices in the bottom.
  • In a heavy skillet over unrelentingly high heat, sear the meat by placing only enough meat in the pan to brown without losing temperature (about two small handfuls). It is important that the meat sear quickly. If you see more than a tablespoon or two of juice collecting in the pan, too much meat has been added (or the flame is too low).
  • As the meat is browned, transfer to the stewpot and stir with the dry spices. In between loads of meat, allow the juices to reduce and thicken. Be sure to use a little olive oil during the searing.
  • When all the meat has been browned and transferred to the stewpot, add a little more olive oil to the pan and toss in the diced vegetables (onions, bell pepper, celery and garlic. Cook these until softened and translucent and transfer to the stewpot.
  • Add the tomatoes and anything else left over (there shouldn’t be anything else left over) into the stewpot. Bring it to a boil and then place into a 350 degree oven for 4-5 hours.
  • Serve with crumbled Stilton and sour cream, with some rice on the side.

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Toby Alan Dion Head Geek

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