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A childhood favorite gets an upgrade! These sloppy joes are just what you remember having as a child, but with a grown-up taste.
Preheat oven to 400ºF. Line a baking sheet with tin foil.
Spread onion, celery, and bell pepper evenly on the baking sheet. Drizzle 1/2 tablespoon olive oil over them and drop tomato paste on the baking sheet. Lightly toss the veggies with the tomato paste (the oil will help it spread around) until evenly coated.
Carefully slice off the very top of the garlic so that most of the cloves are exposed. Drizzle ½ tablespoon of olive oil over the top and then wrap the garlic in tin foil. Place it on the baking sheet with the rest of the veggies. Roast all of it for about 40 minutes or so. Remove them from the oven to cool.
While the veggies are cooling, heat remaining tablespoon of olive oil in a large pan over medium heat. Add ground beef and Italian seasoning and cook, breaking beef apart with a spatula, until browned. Add red wine and boil until most of the liquid has evaporated.
Once veggies are cool enough to handle, chop them up until they are in small pieces. Add them to the pan with the ground beef and stir.
Gently squeeze garlic to remove the roasted cloves. Run your knife through the cloves until they are paste-like (use the back of your knife to mash them if needed). Add them to the pan and give it all a good stir.
Add chicken stock, tomato puree, Worcestershire sauce, and brown sugar to the pan. Bring it to a strong simmer and reduce the heat to medium-low. Let is simmer for at least 20–30 minutes, or until sauce has thickened. Check for seasoning and add salt and pepper to taste (I added about ½ teaspoon of salt and a few turns of the pepper mill).
Serve on buns.
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