Brush the grill with olive oil, and season the chicken with salt, pepper (optional-add fresh rosemary) Grill them until no longer pink in the middle. Remove to a plate.
Season kale with salt and pepper and drizzle with olive oil. Grill kale until wilted, about 2-3 minutes.
Add kale to a large bowl with tomatoes, garlic, and cucumber.
Whisk together 4 Tbs olive oil, red wine vinegar and a pinch of salt and pepper. Toss salad with dressing. Serve the chicken with the kale salad.