Start by making your chutney: combine all of the ingredients, except the raisins, in a large saucepan. Bring to a boil, lower to a simmer, stirring occasionally, and cook for 50 minutes to an hour until most of the liquid is evaporated. Take off the heat and add the raisins.
To make the squash, heat the oven to 425. Slice the squash in half lengthwise, scoop out the seeds, and slice into 1/2 inch rings. Toss on a cookie sheet with the maple syrup, enough olive oil to coat everything, and lots of salt and pepper. Roast in the oven for 20 minutes, flipping halfway through, until the squash is deep golden brown on both sides.
To make the chops, grind the coriander seeds, fennel seeds, and peppercorns in a spice grinder just until coarsely ground (you don't want a powder or it'll burn). Season the chops all over with lots of salt and the spice mixture.
In a large cast iron skillet, heat a splash of the grapeseed oil until very hot. Lay the chops in on their side with the fat-side down. Render the fat until golden brown, then lay the chops flat in the skillet -- they should sizzle -- and cook, without moving, for 2 to 3 minutes until deep, dark brown. Flip over and cook on the other side. Start taking the chops' temperature in the middle -- you're shooting for 135. Keep cooking, flipping every few minutes, until you reach that temperature.
Remove the chops to a plate and let rest for 5 to 10 minutes. Serve with the squash and lots of the chutney.