In 1969 the Cubs, managed by Leo Durocher, built a substantial lead in the newly created National League Eastern Division by mid-August. Ken Holtzman pitched a no-hitter on August 19, and the division lead grew to 8 1⁄2 games over the St. Louis Cardinals and by 9 1⁄2 games over the New York Mets. After the game of September 2, the Cubs record was 84-52 with the Mets in second place at 77-55. But then a losing streak began just as a Mets winning streak was beginning. The Cubs lost the final game of a series at Cincinnati, then came home to play the resurgent Pittsburgh Pirates (who would finish in third place). After losing the first two games by scores of 9-2 and 13-4, the Cubs led going into the ninth inning. A win would be a positive springboard since the Cubs were to play a crucial series with the Mets the very next day. But Willie Stargell drilled a 2-out, 2-strike pitch from the Cubs' ace reliever, Phil Regan, onto Sheffield Avenue to tie the score in the top of the ninth. The Cubs would lose 7-5 in extra innings. Burdened by a four-game losing streak, the Cubs traveled to Shea Stadium for a short two-game set. The Mets won both games, and the Cubs left New York with a record of 84-58 just 1⁄2 game in front. Disaster followed in Philadelphia, as a 99 loss Phillies team nonetheless defeated the Cubs twice, to extend Chicago's losing streak to eight games. In a key play in the second game, on September 11, Cubs starter Dick Selma threw a surprise pickoff attempt to third baseman Ron Santo, who was nowhere near the bag or the ball. Selma's throwing error opened the gates to a Phillies rally. After that second Philly loss, the Cubs were 84-60 and the Mets had pulled ahead at 85-57. The Mets would not look back. The Cubs' eight-game losing streak finally ended the next day in St. Louis, but the Mets were in the midst of a ten-game winning streak, and the Cubs, wilting from team fatigue, generally deteriorated in all phases of the game. The Mets (who had lost a record 120 games 7 years earlier), would go on to win the World Series. The Cubs, despite a respectable 92-70 record, would be remembered for having lost a remarkable 17½ games in the standings to the Mets in the last quarter of the season.

Who managed the Cubs in 1969?