- Jerkass Woobie: Bruce. He's cold, distant, ruthless, and tyrannical. But when Jonathan Poe and his teacher come into the chess club, Bruce is appalled to learn that Jonathan isn't getting proper schooling, and Jonathan's teacher gets in a not-so-subtle dig in at Bruce, saying that Jonathan is a lot like Bruce used to be, except that Jonathan, "never quits." Later on, when Josh and his family are about to go to Chicago, Bruce goes to Fred and warns him that if they haven't prepared Josh properly, and Josh ends up getting crushed, "it will destroy him, and there will be nothing left. You don't know what that can do to a person." Fred looks Bruce in the eye and says, gently, "I think I do."
- Jonathan can also count. He's rude and obnoxious, but it's clear that he has been molded this way by an uncaring teacher. After Josh wins the tournament, Jonathan is heartbroken. The difference is, if Josh had lost, he would still have a caring family and friends (and a proud teacher) to prop him up. Jonathan has no one. There is a faint ray of hope for Jonathan; after the tournament, you can see Jonathan turning away from his teacher; perhaps he has woken up to the fact that this is not the way for him to live his life. (It is notable that Jonathan's real-life counterpart, Jeff Sarwer, has indeed turned out to be a well-adjusted adult, in spite of the abuse he suffered as a child.)
- Protagonist Title Fallacy: Despite the title containing the name "Bobby Fisher", the main character is really Josh Waitzkin.
- Self-Deprecation: The trainer Pandolfini comes over as a total Jerkass (although he claims he just does what he has to do to make Waitzkin a great player - the whole drama is based on this conflict). Well, Pandolfini was the films chief chess consultant...
YMMV / Searching for Bobby Fischer