To prepare the squash, I tossed 1-inch cubes of fresh butternut squash with olive oil and spread them out on a parchment lined large baking pan and then seasoned them with sea salt and black pepper. I popped them into a 400 degree oven for about 30 minutes and then raised the oven temp to 425 degrees and cooked them for about another 10 minutes so they would get nice and brown and caramelized.
While the squash was in the oven, I seasoned my steaks with sea salt and black pepper on both sides. I added a couple tablespoons olive oil and couple tablespoons butter to a heavy dutch oven (you could also use an ovenproof skillet or cast iron skillet since it gets finished in the oven). I heated the oil and butter over medium-high heat and added the 1-1/2" thick steaks and cooked them for approximately 8 minutes on one side until they were nice and browned, then turned them over and cooked for about 5 minutes on the other side. I then placed them in a 425 degree oven to cook for approximately 10 minutes and turned the heat off and let them sit for about 5 minutes or so in the hot oven. They came out cooked medium to medium-well (a thin line of pink inside). I'm not crazy about rare meat but don't mind a little pink inside. Simply increase or decrease the cooking time depending on whether you like your steak more or less done and also depending on the thickness of your steaks. These steaks turned out so tender and juicy.
I snapped a couple of quick photos of tonight's meal below. Enjoy!