Season the chicken: Pat the chicken dry. Sprinkle with salt, pepper, oregano, dried basil, and red pepper flakes if using.
This gives the chicken a head start on flavor.
Optional sear for deeper flavor: Heat 1 tablespoon olive oil in a skillet over medium-high heat. Sear chicken 2β3 minutes per side until lightly browned. Transfer to the crockpot.
If skipping the sear, add the chicken directly to the crock.
Build the sauce base: Add sliced onion and garlic to the crockpot. Stir in crushed tomatoes, tomato paste, chicken broth, olives, capers, remaining 1 tablespoon olive oil, and vinegar. Nestle the chicken into the sauce so itβs mostly submerged.
Cook low and slow: Cover and cook on Low for 5β6 hours or on High for 2.5β3.5 hours.
Chicken should be tender and easily pulled with a fork but not falling apart into shreds unless you prefer it that way.
Finish with fresh herbs: In the last 15 minutes, stir in the torn basil and parsley. Taste and adjust with salt, pepper, or a splash more vinegar for brightness.
Serve: Spoon the chicken and sauce over pasta, rice, or quinoa. Or serve with toasted bread to mop up the sauce.
Top with extra basil and a sprinkle of Parmesan or feta if you like.