Lilly last pitched for the team that originally drafted him on June 4, 2014. He finished his career with a 130-113 win-loss record, a 4.14 earned run average, and 1,681 strikeouts. During the spring of 2014, the Chicago Cubs hired him as an assistant. Lilly is married to his wife, Natasha, who works at a veterinarian. The couple is active in animal rescue and advocacy. They have one child together, a son named Theodore Roosevelt Lilly IV, who was born in 2010.