Picadillo-Style Sheperd’s Pie with Chipotle Mashed Potatoes (from Weight Watcher’s)

This is a pleasant twist on sheperd’s pie with the sweet and savory flavors of picadillo in place of regular beef.  I like picadillo and I like sheperd’s pie, so when I stumbled upon this recipe that brought both together, I HAD to try it!  The result was delicious and the aromas floating through the house as it cooked just made my stomach growl with anticipation!


  • 1 pound lean ground beef
  • 1/4 tsp
  • 2 teaspoon canola oil
  • 1 onion chopped
  • 1 small zucchini, diced
  • 1 small yellow squash, diced
  • 2 garlic cloves, minced
  • 1 (14 1/2 oz) can diced tomatoes
  • 2 1/2 tablespoons golden raisins
  • 12 pimento stuffed olives, chopped
  • 1 tsp ground cinnamon
  • 1 teaspoon ground cumin
  • 1.5 pounds red potatoes, cut into 1-inch cubes
  • 1 tablespoon butter
  • 1/4 teaspoon salt
  •  1 tablespoon chipotle chilies in adobo, chopped.


  1. Preheat oven to 375 degrees F. In a large pot filled halfway with water, bring to a boil.  Add potatoes and cook until tender.  drain water and return potatoes into pot.  Mash potatoes with a potato masher, add butter and 1/4 tsp salt, mix and set aside.
  2. In a large skillet, over medium high heat,  add beef and 1/4 tsp salt; cook, breaking it apart with a spoon, until browned, about  10 minutes.  Transfer to a large bowl.
  3. Add oil to skillet, add onion and garlic and cook, for about 1 minute.  Add zucchini and squash, stir and cook until vegetables are softened, about 6 minutes.  Return beef to skillet, stir in tomatoes, raisins, olives, cinnamon, and cumin.  Bring to a boil.  Remove skillet from heat and transfer mixture into a 2 quart casserole dish.
  4. Mix together mashed potatoes and chipotle.  Spread potato mixture over beef mixture.  Transfer casserole to oven and bake until potato is browned and filling is bubbly along the edge, about 25 minutes.  Let stand 5 minutes before serving.


  • The original recipe called for 1 (24 oz) package refrigerated mashed potatoes, but I find I don’t like the taste so I opted to make my own.
  • I used regular raisins whole (that’s all I had in the cupboard) instead of golden raisins chopped and it didn’t affect the flavor.
  • The original recipe also called for 8 olives, but the ones I bought seemed small so I used 12.

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