After a number of years of "rebuilding", though they didn't really call it that in those days, the Cubs were true contenders in 1927, featuring Hack Wilson in his first big year (.318/.401/.579 with 30 home runs), and a solid pitching staff anchored by Charlie Root and Guy Bush, who would help lead the Cubs to several pennants beginning in 1929.
The '27 Cubs were in first place most of July and August, and after splitting a doubleheader with the Phillies on August 27 in Philadelphia, they were 73-47, 3½ games ahead with 34 games remaining. That was a lot of time, but...
Well, you can guess what happened next. The Cubs, likely weary at the end of what would be an 18-game road trip (not uncommon in those days, but still), lost seven in a row, 10 of 11, and 16 of the next 23. Instead of being up 3½ games, they trailed by 8½ -- losing 12 games in the standings in three weeks' time.
They righted the ship somewhat with a five-game winning streak, and trailed the first-place Pirates by 4½ games with six remaining as Pittsburgh came to Wrigley Field for a doubleheader Saturday, September 25. The Pirates were to be the Cubs' opponent for four of the six games. They'd need to take all four, a difficult but not impossible task. (And then the Cubs would have had to pass the Giants and Cardinals, too; the Cubs were in fourth place.)
Pittsburgh's Pirates are about to rise and sing, "It won't be long now." The treacherous ground that laid between them and a pennant was just about hurdled yesterday when their class drove them through the Cubs in both ends of a double header before 32,000 customers, who seemed perfectly willing to see the McCarthy gang lose so long as it was the Pirates who were winning. In both struggles the Cubs discovered that on certain days Vic Aldridge and Ray Kremer are fellows who are unbeatable. In the initial encounter Aldridge held his one time mates to four hits, but support, particularly on a catch by Lloyd [Sprout] Waner with two men on base played as prominent a part as the Hoosier schoolmaster's right arm. Kremer was hit a bit harder in the nightcap, but he kept the blows scattered over a wide territory and the Cubs, now mathematically out of the pennant fight and without a chance for third place money, couldn't even make threatening gestures after the Pirate artillery once had swung into action.
In those days, with salaries low, teams that didn't win pennants definitely jockeyed to finish second or third, because those clubs did get a share of the postseason pot, not insignificant to any player, almost all of whom had to take offseason jobs to help make ends meet.
For the Cubs it was the beginning of more than a decade of contending, with four pennants to come. Let's hope the next decade is as kind to the modern Cubs.