Prep the butternut squash by peeling, halving and seeding it; then cut into 1/4" pieces.
In a medium saucepan, cook the squash with the milk, cream and salt over medium heat until very tender, stirring frequently for about 30 to 40 minutes.
Use a slotted spoon to transfer to a highs speed blender and purée until very smooth. If the purée is too thick, add a little of the remaining hot dairy.
Make the Apple Jam Glaze
In a small saucepan over medium heat; combine the apple jam, butter and apple cider vinegar until it just starts to boil.
To cook the pork chops
Preheat your oven to 350 degrees.
Heat a cast iron skillet on medium-high with enough canola oil to coat the bottom, just until it starts smoking.
Season the pork chops with kosher salt and freshly ground pepper.
Sear the pork chops on the first side until browned.
Turn the chops over, reduce heat to medium-low and pour the apple jam glaze on top.
Baste the chops and cook for a few minutes on second side, then transfer to the oven to finish cooking until the internal temperature reaches 140° F.
Rest the pork chops for at least 5 minutes (the internal temp will climb to about 145° F), then serve with the butternut squash purée and top with any of the glaze that is left in the pan.
Notes
Save the extra milk & cream mixture for a soup or mashed potatoes.
The Butternut Squash Purée can be made ahead of time and reheated.