We talked about this in Slack yesterday!
In 2010, which does not predate league 1, but does predate launching Ottoneu with FanGraphs, James Shields had a -75.6 point outing. In 2019, Mike Fiers had a -75.5 start.
Aaron Judge had a cool 47.5 points yesterday, which pales in comparison to Shohei dropping 65.4 last season (3 HR, 2 2B, SB).