What jobs did he hold before his appointment to the District Court? If he was not a judge I don't know how Trump could have been able to predict anything. I didn't bother to look up Tipton's background, but I know plenty of District Court appointees were not previously judges. Even if he was a judge it wouldn't necessarily have provided any clues.
The main thing Trump has to think about in a second go round is who he was depending on the first time around for his judicial appointees and try to figure out a different group of people to rely on.
It’s interesting to note that judges appointed by Democrats never turn out to be conservatives. But plenty of judges appointed by Republicans turn out to be liberals.
Funny how that works out.