Butternut Squash, Kale, and Cheddar Bread Pudding

I’d never actually made bread pudding before this savory version, even though a sweet, boozy bread pudding studded with raisins is one of my all-time favorite desserts. It’s rare that I have leftover bread of any kind, so it felt strange to buy a baguette with the explicit purpose of letting it get stale. Definitely worth it though.

Being a mostly meatless type, I offered to bring a vegetarian entrée to Thanksgiving, letting our marvelous hostess off the hook. While it isn’t even close to vegan or low-calorie, I think I would much prefer this to a Tofurkey. Everyone knows that the sides are the best part of Thanksgiving anyway. And the kale and squash at least gives the illusion of getting in some real vegetables.

My one tip would be to use the sharpest, best cheddar cheese you can find/afford. I skimped on that, and it just wasn’t as good as I know that it could’ve been. Another bonus: this can be made in advance and is probably even best made in advance. I spent nearly a week taking the leftovers for lunch, and it only got better as the flavors melded. Perfect for when your Thanksgiving morning is routinely taken up by running a 5K with your family.

Butternut Squash, Kale, and Cheddar Bread Pudding
source: Ezra Pound Cake

Ingredients

• 2 POUNDS PEELED SEEDED BUTTERNUT SQUASH, CUT INTO 1-INCH CUBES (ABOUT 6 CUPS)
• 3 TABLESPOONS OLIVE OIL, DIVIDED
• KOSHER SALT
• FRESHLY GROUND BLACK PEPPER
• 7 LARGE EGGS
• 2 1/4 CUPS HALF AND HALF
• 6 TABLESPOONS DRY WHITE WINE (OR HARD CIDER)
• 2 TABLESPOONS CHOPPED FRESH THYME (OR 1 TABLESPOON DRIED)
• 1 TABLESPOON CHOPPED FRESH SAGE (OR 1/2 TABLESPOON DRIED)
• 1 TABLESPOON DIJON MUSTARD
• 1 DAY-OLD BAGUETTE (DO NOT REMOVE CRUST), CUT INTO 1-INCH CUBES (ABOUT 8 CUPS)
• 1 CUP CHOPPED SHALLOTS (ABOUT 4 LARGE)
• 2 CLOVES GARLIC, FINELY CHOPPED
• 1/4 TEASPOON CRUSHED RED PEPPER FLAKES (OPTIONAL)
• 2 BUNCHES TUSCAN KALE (ABOUT 1 POUND), RIBS REMOVED, KALE COARSELY CHOPPED (CAN BE SUBSTITUTED WITH SPINACH)`
• 8 OUNCES EXTRA-SHARP CHEDDAR CHEESE, COARSELY GRATED

Preparation

1. Preheat oven to 400 degrees F. Place squash and 1 tablespoon oil in a large bowl; sprinkle with salt and pepper, and toss to coat. Spread out squash cubes on a large rimmed baking sheet. Roast until squash is tender, stirring occasionally, about 25 minutes. Set aside.
2. Reduce oven temperature to 350 degrees F.
3. Whisk eggs in large bowl. Continue whisking as you add half and half, wine, thyme, sage, mustard, 1 teaspoon kosher salt, and 1 teaspoon freshly ground black pepper. Add baguette cubes to the egg mixture, and gently fold them into the mixture to coat each side. Let the baguette pieces soak 30 minutes, stirring occasionally.
4. Meanwhile, heat 2 tablespoons oil in large pot over medium heat. Add shallots, garlic, and crushed red pepper flakes, and sauté until soft and fragrant, stirring frequently, about 5 minutes. Add kale; cover and cook 2 minutes. Uncover the pot, and stir until kale is wilted but still bright green, about 5 minutes (the kale will still be a little crunchy).
5. Generously butter a 9-by-13-inch baking dish. Using slotted spoon, transfer half of bread from egg mixture to the dish, spreading evenly. Spoon half of kale over the bread layer. Spoon half of squash over the kale layer, and sprinkle it with half of the cheese. Repeat with remaining bread, kale, squash, and cheese. Pour the remaining egg mixture over the bread pudding.
6. Cover bread pudding with foil, and bake for 20 minutes. Remove foil; bake uncovered until custard is set, about 20 minutes longer.
7. Preheat broiler; broil pudding until cheese browns slightly, about 2 minutes. Cool 5 minutes and serve.

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