Preheat oven to 400°. Season squab with Chinese five-spice and refrigerate. Over medium high heat, begin to brown wings, legs and bones in peanut oil. Place sauté pan into the oven and roast until all is a rich, uniform color (approx. 15 min.). Carefully place bones in a 4 to 6 quart sauce pan.
Pour off all but 2 tablespoons of the rendered fat and return to medium heat. Add shallots, celery and carrot and carefully brown. Add the tomato paste, thyme, parsley and bay leaf to the sauce pan.
Pour off all fat from the sauté pan and add the Cabernet Sauvignon and orange juice. With a wooden spoon, carefully scrape flavorful “fond” from the bottom of the pan. Add wine “fond” to the sauce pan. Add water, just to cover. Gently simmer for 2½ to 3 hours, then strain stock and reduce by two-thirds.
Season squab with kosher salt. Add butter to a sauté pan, and brown squab on both sides. Place pan in oven and roast for 6 to 7 minutes or until just firm to the touch. As squab rests, bring sauce back to a simmer. Whisk in butter and adjust with salt and vinegar to your liking.