For the hotdish filling: 

1. Heat 2 Tbsp canola oil in a large pot over medium high heat. Add the brisket, season with 1 1/2 tsp salt and a few turns of black pepper, and cook until browned on all sides, about 10 minutes.
2. Reduce the heat to medium and add the onion, carrots, and celery and cook, stirring, until softened, about 10 minutes.
3. Add the red wine and cook for a few minutes until it’s reduced by half.
4. Add the brown sugar, tomato paste, canned tomatoes, stock, rosemary and apples and simmer uncovered for 2 1/2-3 hours, stirring occasionally, until meat is tender. You want this to reduce and get quite thick and saucy, however if it reduces too far to where it’s more gloopy than saucy, add a bit more stock.
5. Meanwhile, preheat the oven to 375°F. Brush the innards of your squash with the remaining 1/2 Tbsp oil, sprinkle with 1/4 tsp salt and a few turns of pepper, and roast until a fork pokes easily into the center, begin checking at 1 hour.
6. Puree the squash and then stir it into your hot dish mixture with crushed red pepper. Taste and adjust seasoning.
7.  Increase the oven heat to 400°F. Transfer the mixture to an 8” by 12” casserole dish and top with latkes lined up in neat rows. Bake until the mixture is bubbly and the latkes are deep brown, about 45 minutes. Let cool slightly before serving.

For the latke topping:

1. Shred the potatoes and onions in a food processor or with a grater or mandoline. Place in a strainer that’s been lined with cheesecloth. Toss with salt and let sit over a bowl for 30 minutes. Gather the top of the cheesecloth and then use your hands to squeeze out as much excess moisture as you can.
2. Transfer to a bowl and mix in the eggs, lemon juice, flour, and a few turns of black pepper.
3. Heat a skillet with a 1/4” oil until shimmering. Working in batches so as not to crowd the pan, fry up loosely packed rounded tablespoons of the latke mixture until browned on both sides. Add more oil to the pan as needed. Transfer to a paper towel-lined plate and set aside until ready to use.