Chessie System History The C&O-B&O Unity, the beginning of the Chessie System SEAtkinson, February 9, 2025February 18, 2025 The start of the C&O – B&O relationship in May, 1960 put into motion the spin toward the Chessie System as a holding company led by the C&O.for the purpose of diversifying the C&O. What begin in May 1960 was the beginnings of the Chessie System Railroads. Continue Reading