1 1/2 cups tawny port
2 tablespoons white truffle oil, plus more to taste
1/8 teaspoon truffle salt
Pinch of sugar
1/2 cup high-quality mayonnaise
1 tablespoon white truffle oil, plus more to taste
1 small clove garlic, minced
2 tablespoons fresh lemon juice
Vegetable oil, for brushing
1 1/2 pounds coarsely ground beef (ask your butcher for a blend of top round and brisket, if possible)
4 slices Il Boschetto al Tartufo or other truffle cheese
4 brioche or Portuguese buns, split
Unsalted butter, melted, for brushing
Make the glaze: Bring the port to a simmer in a small saucepan over medium-high heat. Cook until slightly reduced and syrupy, about 10 minutes. Remove from the heat and whisk in the truffle oil, truffle salt and sugar; add more truffle oil to taste. Let cool slightly.
Make the aioli: Whisk the mayonnaise, truffle oil, garlic and lemon juice in a small bowl; add more truffle oil to taste. Set aside.
Cook the burgers: Preheat a cast-iron or other heavy-bottomed skillet over high heat. Lightly brush the skillet with vegetable oil. Form the beef into four 3/4-inch-thick patties, 4 inches each. Cook until the bottoms are seared, 4 to 5 minutes. Flip and cook about 4 more minutes for medium. Top each burger with a slice of cheese and let melt, about 1 more minute; remove to a plate. Brush the cut sides of the buns with melted butter and toast in the skillet, 30 seconds to 1 minute.
Spread the aioli on the bottom buns; top with the burgers. Whisk the glaze and drizzle over the burgers; cover with the top buns.
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