Sear each medallion until desired temperature is reached. Remove from pan and reserve for service. In the hot pan, begin to saute the squash utilizing the fond (brown bits in the pan). Serve as a side for the filet. Serve with Triple Mashed Potatoes.
Triple Mashed Potatoes:
Separate the sweet and Yukon potatoes into 2 sauce pots and cover with cold water. Season the water with salt and freshly ground black pepper and bring to a boil. Add 1-ounce of chipotle to the sweet potato water. Cook the potatoes until they are fork tender. Drain them and transfer into separate bowls. Add the garlic to 1 bowl, and the red pepper to the other bowl of Yukon potatoes. Transfer the potatoes 1 style at a time into a potato ricer and rice into a bowl. Combine the butter and cream to make mashed potatoes. Continue this process with each flavor and hold the potatoes until service.
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