When you settle instead of fight a lawsuit you send a message to others that you might be prone to settling more lawsuits instead of fighting. It's a weak message. It encourages more lawsuits against you. That's why he doesn't do it. He deals with hundreds or thousands of lawsuits, both as plaintiff and defendant, so if he's viewed as soft, which he is not, he would see dozens more lawsuits coming against him.

It's the same with foreign government kidnapping ransoms. If you take a weak stance that you will cave in, it encourages more of that behavior against you. Additionally, if you pay ransoms, that funds more ransoms and the cycle continues. As a policy, the U.S. does not pay ransoms to terrorists, as heartbreaking as having someone like James Foley die can be.

Trump's well known for fighting lawsuits in general but a USA Today report found that he does tend to settle personal injury suits on his properties fairly often. This is because actuaries and legal consultants find those to have far greater variance with jury awards - they're much more of an unknown quantity so companies tend to settle those because of the wild card factor. It's difficult to gauge how much Grandma will get from slipping on a hotel floor and breaking her hip. A tearful jury could award quite a bit, the variance is much higher with personal injury.