In a large bowl, add the chicken, cover with wine, and set aside.
Quarter the potatoes, leaving the skin-on. Place in a large pot, cover with water and bring up to a boil over medium heat. When the potatoes are cooked, drain and place in a medium bowl. Mash the potatoes, season with salt and set aside.
In a small pot, combine apple and cream and reduce over medium heat 15 minutes.
Drizzle olive oil in a large skillet over medium high heat, add the bacon and crisp 3 to 4 minutes. Remove to a plate.
While bacon crisps, remove the chicken to a work surface, reserving the wine. Cut chicken into large bite-size pieces, season with salt and pepper, dredge in flour then brown in bacon drippings. While chicken browns chop vegetables. Remove the chicken to a plate, then add 2 tablespoons olive oil to the skillet, season the vegetables with salt and pepper and add bay leaf and thyme. Cover pan to sweat vegetables 5 minutes then remove lid, stir in 2 tablespoons flour, cook 1 minute then stir in wine, add chicken back to pan and simmer together to thicken and the chicken is cooked through, a couple of minutes more.
To a food processor, add the apple-cream and brie, process until smooth and season with salt. Combine apple-brie mixture with the mashed potatoes.
Serve chicken with wine over brie mashed potatoes.