Legal Love Troubles
Redstone's children weren't the only ones who battled it out with him. The magnate was also taken to court in 2016 by ex-girlfriend Manuela Herzer (42 years his junior), who claimed that he was incompetent and had become "a living ghost." Her lawsuit also made the shocking allegation that Redstone, in his 90s, demanded steak and sex every day - um, definitely against his doctor's orders. Weirder than that, however, is that dude had not one but two live-in girlfriends - in addition to Herzer, there was Sydney Holland. They both had rule over his L.A. mansion, and were accused by household staff of being mentally and financially abusive to him.
The case brought on by Herzer was eventually dismissed when Redstone recorded a video as testimony against Herzer, calling her a "fucking bitch" and saying he didn't want her anywhere near him. Yowza.
Nevertheless, questions surrounding his competency led, that same year, to his stepping down from chairman roles in CBS and Viacom. But he never lost his ruthless charm. As late as 2018 he was reported to have used an iPad to communicate recordings of his voice saying, "yes," "no," and "fuck you." If that's not Logan Roy material, we don't know what is.