James Pickens Jr. – Richard Webber Then
Dr. Richard Webber, the first Chief of Surgery at Seattle-Grace, was known as The Big Boss. Despite his intimidating presence, he was kind to the terrified interns. Having worked with Meredith's late mother, he recognized Meredith had inherited her mother's medical talents.
Dr. Webber lost his wife, got electrocuted, and assisted Meredith with insurance fraud, leading to his temporary firing. He continues to roam the halls of Grey Sloan Memorial, remaining the glue that holds Grey's Anatomy together.
