Heat 1 tablespoon olive oil in a large nonstick skillet over medium-high heat. Season the pork with salt and pepper and add to the skillet. Cook until browned and just cooked through, about 3 minutes per side. Remove to a plate and loosely cover with foil to keep warm.
Wipe out the skillet and heat 1 more tablespoon olive oil over medium-high heat. Add the corn, red onion and 1/2 teaspoon salt. Cook, without stirring, until the corn starts browning, about 3 minutes. Stir and continue cooking until charred and tender, about 2 more minutes. Add the garlic and red pepper flakes and cook until softened, about 30 seconds. Stir in 2 tablespoons vinegar and the honey; remove from the heat.
Combine the arugula and the remaining 2 tablespoons olive oil and 1 tablespoon vinegar in a large bowl. Season with salt and pepper and toss. Divide the pork and arugula among plates. Stir the basil into the corn mixture and spoon over the pork.