His first wife, Minnie, did get pregnant but it was an ectopic pregnancy and ended at 6 weeks. She was still able to have children but never did. According to Lisa Stein's bio, Syd may have impregnated actress Lucille Ricksen, who would have only been 14 or 15 years old. She died in 1925 and gossips at the time thought it was from a botched abortion that Syd arranged, but her death certificate stated that she died from tuberculosis.
There's no evidence that she died of a botched abortion (her death certificate says otherwise)–or that she was ever even pregnant. Syd got into much worse trouble with a woman a few years later when an actress named Molly Wright accused him of sexual assault (he bit off one of her nipples during sex). She filed charges against him that were settled out of court. This incident put an end to Syd's film career.
I remember reading that when Lisa Stein Haven was writing her Sydney bio, she had trouble at times with the darker sides of Syd's personality, but that talking to the Chaplin kids about their memories of Syd as their uncle helped her find his more sympathetic side. This picture kind of captures that, I think.Carrie