Perheat oven to 400 degrees F.

Peel off the loose papery husk on the outside of the garlic head. Slice off the top to reveal the tops of the raw cloves. Drizzle with olive oil and wrap the head of garlic in foil. Roast until caramel colored and tender, about 40 minutes.

Peel the Potatoes and cube into 2-inch pieces. Fill a large pot with cold water and add Potatoes and bay leaves. Bring the water to a boil and continue to simmer until Potatoes are just fork tender, but not falling apart.

Completely drain the Potatoes and place it back on the heat. Keep the burner on the lowest setting until the Potatoes have completely dried out. The dryer the Potatoes, the more liquid they will reabsorb. Remove the bay leaves at this time. 

Using a ricer of Potato masher, mash Potatoes. Gently squeeze the roasted cloves from the roasted garlic bulb into the mashed Potatoes and mix until smooth.

In a small sauce pan melt butter into the milk until both are hot. Using cold dairy will compromise the texture of the Potatoes. Add the milk and butter to the Potatoes stirring quickly with a large spoon until fully absorbed. Salt and pepper to taste.