Baller, maybe. Thinker, for sure.
If you'd like to truly understand his strategy and game plan, reading the book Winning Ugly would be a great start. Although it is a sort of tennis manual for the recreational player, he uses himself as an example of how as a player he would beat tougher opponents who had more "tennis skills" by using his strengths against his opponents weaknesses.
Most players go into a match just hoping to play well, and they figure that if they play well they will win and if the don't it is more likely that they'll lose. Gilbert knew that this is not the best way to think of a match. He knew that he could beat better players, even if he wasn't playing particularly well that day.
Brad Gilbert would start the match hours or even days before the actual match began. He would do this by sizing his opponent. He would research not only their strengths and weaknesses but also their tendencies and by being prepared for the "outer variables" that one may encounter during a tennis match against specific opponents he was always ready for what was to come.
For example, he knew McEnroe's game probably even better than McEnroe himself. He knew that when McEnroe was down in a match, he would use the crowd to distract his opponents, and basically threw a show which would delay the match, get his opponent to relax and drop their guard and then take control of the match. The funny thing is that his opponents would not even see it coming.
Gilbert knew this "show" was inevitable, and his strategy was to use McEnroe's own strength (getting the crowd riled up) to his advantage. Instead of being upset with McEnroe's showmanship or even worse becoming a part of the audience, Gilbert would keep his focus and would even actually keep hitting some serves or shadow swinging to keep himself from cooling down. When McEnroe would realize his best "shot" didn't work against Gilbert, he had nothing left to win with.
Two more things that Gilbert would do are:
1. He would go to the opponents strength to neutralize it. For example, if his opponent's best shot happened to be the forehand crosscourt, he would hit to the forehand on purpose and would be ready to take the toughest blow from his opponent and basically just block it back. The funny thing about tennis players, is that when they hit their best shot and the ball comes right back, they tend to overhit or under hit the next shot. When a player uses his most powerful weapon and they receive a neutralizing shot back, they tend to not be able to handle it.
2. Gilbert was a master at playing the score. Tennis is a mental game, most of the match is won between points and every player has to fight in an emotional battle. Gilbert had a way to strategize each point depending on the score to maximize his chances of winning. For example, anytime the score reads 30-something, players are faced with what he called a "set up" point, and the best way to deal with a situation where the score has "30" on it, is to play a traditional point. First serve in, no drop shots, no lobs, no funky business, just play a high percentage point and taking his strength (forehand) to their weakness (backhand). If his opponent threw a winner, then so be it, Gilbert was not about to lose any set up points for going for broke or trying something fancy. By winning more "set up" points and set up games (when game score reaches 4) than his opponents, Gilbert would always have an overall advantage in a match.
Ultimately Gilbert would always do what most tennis players are reluctant to do. Mental homework.
