In a large mixing bowl, season the chicken thighs with the 1st quantities of salt and pepper. Toss the chicken to coat evenly with the seasonings. Allow to sit while you heat the vegetable oil in a large skillet over medium-high heat. **This step is optional, but highly recommended. If you prefer not to sear the chicken skin, skip ahead to step 3.
Place the chicken thighs into the hot oil, skin side down. Sear the chicken for 4-6 minutes, or until the thigh releases from the pan with little to no resistance when you try to move it. Flip the thigh over and sear for 4 minutes on the other side. Sear the thighs in small batches to ensure a proper sear. Remove to a plate to hold while you sear the remaining thighs.
In a casserole, or roasting pan, add the chopped kale. Pour the olive oil over the kale, evenly, and use your hands to massage the oil into the leaves. Top with the cut squash and the garlic cloves. Season the vegetables with a tsp of kosher salt and 1/4 tsp of black pepper (and dried thyme if you're not using fresh). Toss again to make sure everything is seasoned evenly.
Top the veggies with the chicken thighs, leaving a 1/2"-1" gap between each piece. If you're using fresh thyme, add the sprigs, making sure to stick some in between the thighs, as well as on top of. You can separate the stems if need be.
Cover the pan with aluminum foil and bake for 45 minutes. After 45 minutes, remove the pan from the oven and increase the oven's temp to a low broil. Remove the foil from the top of the pan and place the pan back into the oven to crisp up the skin. Broil for 5-10 minutes or until the skin crisps. Be careful to watch them closely so they don't burn.
Remove the pan from the oven and allow to rest for 15 minutes before serving. Enjoy!
You can bulk up this meal with a side of mashed potatoes or steamed rice.