The Cubs started 1999 off well in trying to repeat their 1998 playoff appearance. In early June they won a pair of games against the Diamondbacks in Arizona, going into first place with a 32-23 record.
The next day, Lance Johnson got picked off to end an 8-7 loss to the D'backs. The Cubs proceeded to lose 10 of 11 and went into freefall. At one point in midsummer they lost by scores of 17-6, 19-12, 14-1 and 21-8 -- in a five-game span.
August brought, at one point, 11 losses in 12 games, and then the Giants came to town to open a four-game series on a Monday evening. Paul Sullivan sums up what happened in his Tribune "recap" of... well, read on:
What's a rain delay without rain? Just another day at Wrigley Field, where the strangest things have been happening in 1999. The Cubs-San Francisco Giants game was delayed for 3 hours 45 minutes Monday night before finally being postponed, though the rain did not begin until at least 1 1/2 hours after the scheduled 7 p.m. start. The mere "threat of rain" was enough for the Cubs to delay the start, an unfortunate occurrence for children on the eve of the first day of classes for Chicago public schools. Monday's rainout will be made up as part of a double-header Wednesday.
I was at this, uh, event. It was bizarre. At 7:05, the scheduled starting time, it was not raining. It didn't start raining until around 9:20 (a little later than Sullivan's "1 1/2 hours"), which would easily have been enough time to play six or maybe even seven innings and get an official game in. At one point, our bleacher group discovered that they had Ron Santo on WGN radio with fans during the delay, so I called in and they put me on the air to talk with Santo, who couldn't believe that they weren't playing. Even in those pre-smartphone days, I knew that once it started raining, it wasn't going to stop, so I left the park when the rain began to fall. The umpires waited another hour or so before giving up.
At the time, the night-game ordinance did not allow the Cubs to play split doubleheaders, so they were forced to make this game up as part of a single-admission doubleheader, as noted by Sullivan, two days later. (The Giants swept the twin bill.) The three other dates in that series drew 25,501, 26,584 and 28,351, so you can probably assume there was a house of at least 25,000 on hand for that Monday night game, for which the Cubs had to issue refunds.
It was estimated by some that the cancellation of the date cost the Cubs about $1 million, a not-insignificant sum even by 1999 baseball standards (the Cubs' payroll that year was about $55 million). Rumors were that this was one of the factors that contributed to general manager Ed Lynch's dismissal midway through the next season.
August 1999 was the worst calendar month in Cubs history, as they went 6-24. The non-rain delay was a laughable symptom of the horribleness that was the 1999 season, where the Cubs went 35-72 after that 32-23 peak. That 107-game stretch, and one of identical length in 1966, are the worst such runs in club history.