Trump has launched 3 cases where he did not obtain a court judgment after trial, but the lawsuits were resolved in his favor via settlement payments.
Many of Trump’s other lawsuits such as his suits against The Wall Street Journal, The New York Times, CNN, and others, are ongoing or have been dismissed by courts, struck down, or otherwise not yet resulted in a victory. For example, his defamation lawsuit against The New York Times was thrown out by a judge (with a chance to amend) - not a win.
There seem to be at least half a dozen notable Trump lawsuit losses or dismissals that have also been reported.
I know less than nothing about American law but my question would be, is his modus operandi simply to chance his arm? I wonder where the money keeps coming from to do that?