Heat 2 skillets each with 1 tablespoon EVOO over medium-high heat. Season chicken with salt and pepper and add to first skillet, cook chicken 12 minutes, turning once.
Meanwhile, add bacon to second skillet. While bacon cooks, halve trimmed leeks lengthwise then slice 1/2 inch thick and vigorously wash in a colander then dry on kitchen towel. Add leeks to bacon and saute to soften 5-7 minutes. Sprinkle flour over the leeks 1 minute. Stir in stock and tomatoes and reduce heat to a simmer.
When chicken is done remove to platter and deglaze the pan drippings with wine, scraping up the bits and color 30 seconds, pour drippings into the gravy pan, stir to combine.