• Preheat the oven to 350°F.

Roast the Garlic:

• Trim the top 1/4-inch off the head of garlic and place on a piece of foil, cut side up. Drizzle with olive oil and a pinch of kosher salt.
• Wrap in the foil and roast for 40 to 60 minutes until the garlic cloves are brown and tender.
• Remove from the oven and let cool.

Meanwhile, Cook the Potatoes:

• Add the potatoes to a large pot and cover with water. Add 2 teaspoons salt and bring to a boil. Cook until the potatoes are very fork-tender, about 15 minutes.
• Once the potatoes are tender, drain the potatoes and let sit in the colander to release the steam (this will help to have any excess moisture removed).
• After moisture has been released, add to a large mixing bowl (if using a hand-held mixer) or a stand mixer fitted with the whisk attachment.
• Once the garlic is cool enough to handle, squeeze out the cloves into the mixing bowl with the potatoes.
• Add the butter, milk, and broth and whisk on medium-low speed until smooth and most of the liquid has been absorbed. Add the remaining 2 teaspoons of salt and black pepper and whisk again on medium-low speed until the potatoes are well-whipped and creamy.
• Add the chives and gently fold into the potatoes. Serve immediately.