Heat 2 tbsp olive oil (30 ml) over medium. Add 2 crushed garlic cloves (2), smashing and swirling until fragrant and lightly colored.
Add the tomatoes and juice (800 g), breaking them up. Reduce to medium low and cook 30 min, stirring and crushing occasionally until thick.
Meanwhile, in a mini food processor pulse 3 garlic cloves (3) with 1/4 tsp salt until minced, add pine nuts (2 tbsp) and grind. Add basil (25 g), blend, then drizzle in olive oil (30 ml) with machine running to a thick paste.
Stir pesto into the warm sauce, add Parmigiano (25 g) and black pepper. Serve over fresh pasta.