On the field, the Cubs were a mess in 2000. They got off to a bad start, then a 17-9 July helped put them just six games under .500 by August 2 (50-56). From there, though, they went a staggeringly bad 15-41 to finish with 97 losses.
There was a July selloff, too.
March 23: Acquired Gary Matthews Jr. from the Padres for Rodney Myers
Myers had a decent 1999 for the Cubs, but posted negative (-1.1) bWAR in San Diego with a 5.48 ERA in 54 games over three seasons.
The Cubs didn’t seem to know what to do with Sarge’s son.