Preheat oven to 450 degrees F.
Place a pot of water on the stove and bring to a boil for the pasta. Salt water, add pasta and cook to just-shy of al dente. It needs to have a real bite left to it because it will sit in the sauce for 2 minutes later on and continue to cook. Heads up: you will need 2 ladles of starchy cooking water just before draining, about 1 1/2 cups.
Place the grape tomatoes on a cookie sheet with the garlic. Coat the tomatoes and cracked garlic with 3 to 4 tablespoons extra-virgin olive oil and season with lots of salt and pepper. Roast 20 minutes.
Season the steaks with salt and pepper. Rub with a clove of cut garlic. Coat the steaks lightly in extra-virgin olive oil.
Chop the scallions, whites and greens. Thinly slice the sage and finely chop the parsley. Combine the scallions and herbs with the Gorgonzola crumbles.
When you are a few minutes away from taking the tomatoes out of the oven, heat a skillet over high heat. Add the steaks and caramelize the meat on both sides, a minute and a half per side should do it.
Take the tomatoes and garlic out of the oven. Turn the oven off. Top the meat with the gorgonzola and transfer the skillet to the oven. Let the meat sit in the hot oven 4 to 5 minutes. The Gorgonzola will melt down over the meat and the steaks will be tender and pale pink inside.
Remove the roasted garlic from the skins and mash into a paste with the side of your knife. Transfer the garlic paste to the bottom of a pasta bowl. Using a fork, mix the garlic into 2 ladles of starchy pasta cooking water, about 1 1/2 cups. Add the tomatoes to the bowl and mash them with a potato masher until a sauce forms and tomatoes are well combined with garlic broth. Add penne, grated cheese, arugula and basil and toss a minute or 2 to allow the pasta to soak up flavors.
Serve meat with pasta alongside.