Preheat the oven to 375˚F (190˚C). Line a baking sheet with parchment paper.
Cut off the top third of pumpkin. Remove the pumpkin seeds and pulp (reserve the seeds for another use).
Drizzle the inside of the pumpkin with 1 tablespoon of olive and sprinkle with a pinch of salt.
Place the pumpkin on the baking sheet and bake for 20 minutes until slightly softened.
While the pumpkin is baking, make the chili: Heat the remaining tablespoon of olive oil in a large skillet with a lid over medium heat, until shimmering. Add the onion and garlic, and sauté for 2 minutes, until translucent.
Add the ground beef and cook until browned, 7-10 minutes.
Add the kidney beans, tomatoes, tomato paste, salt, pepper, chili powder, paprika, cinnamon, cumin, and water, and stir to combine. Cook for 5 minutes.
Reduce the heat to low, add the cream cheese and 1 cup of Monterey Jack, and stir until incorporated. Remove from the heat.
Once the pumpkin is done baking, remove from the oven and turn the oven to broil.
Carefully pour the chili cheese dip into the pumpkin. Sprinkle the remaining cup of Monterey Jack cheese on top, all the way to the edge of the pumpkin.
Return to the oven and broil for 2-4 minutes, until the cheese is golden brown. Watch carefully to make sure it doesn’t burn.
Remove the pumpkin from the oven and let cool for 5 minutes. Using oven mitts or kitchen towels, carefully move the pumpkin to a serving platter.
Top with chopped chives and serve with chips and crudités for dipping.