No, reaching a settlement is not considered "winning" a suit. Companies generally settle when their legal fees for going to court would exceed the amount of the settlement. Since we know the rates that WaPo's lawyers charge, we can put a theoretical cap on the amount of the settlement. Less his own legal fees, Sandmann might have walked away with $25,000.
As for "most of them dismissed," 30 of 33 claims against WaPo were dismissed. In other words, Sandmann lost on 30 claims, and settled on 3 of them. Two of his other lawsuits were dismissed by the court, and the only lawsuit still alive is the NBC suit. That's not a legal victory; a motion to dismiss at this stage of a lawsuit assumes that everything the plaintiff said is true without taking into consideration any competing facts.
"No, reaching a settlement is not considered "winning" a suit. Companies generally settle when their legal fees for going to court would exceed the amount of the settlement."
I was going to write exactly this but didn't because it seemed too obvious to do so. The plaintiff ALSO has legal costs if they go for a ruling. This is why I said a settlement is usually considered a victory. If both parties already agree on the outcome then going trough the legal procedure is a waste of time and money. Only if sandmann's lawyers didn't agree on the settlement money then it would be advantageous to push for a ruling. Hence this could be considered 'winning' the suit even though there is no such thing on courts. only rulings(Ex, in favor of) and paying the legal fees of the other party.
As for "most of them dismissed," 30 of 33 claims against WaPo were dismissed. In other words, Sandmann lost on 30 claims, and settled on 3 of them. Two of his other lawsuits were dismissed by the court, and the only lawsuit still alive is the NBC suit. That's not a legal victory; a motion to dismiss at this stage of a lawsuit assumes that everything the plaintiff said is true without taking into consideration any competing facts.