He's had over 3,500 cases, which is excessive. He has great wealth and it has already been established that our court system isn't free of corruption or fairness. If we were to look at the merits of those 'wins', was it due to the facts playing to his favor? Did his overwhelming resources lead to the demise of his opponents?
Source:
http://www.usatoday.com/story/news/politics/elections/2016/06/01/donald-trump-lawsuits-legal-battles/84995854/
Honestly, I don't know the intimate details of those lawsuits and I doubt you do either. What I would like to see is a significant investigative report of his business dealings, along with Clinton. Unfortunately, the media doesn't do that as well as before.