On the other hand, it is extremely unlikely he will get anything near the order of magnitude of what he's asking for, unless the judge well and truly hates, and I mean hates Zuckerberg and facebook. And the appeals judge, and so on, up the chain.
One reason for this is that the judge is going to be weighing on the one hand this guy's thousand dollar investment, and on the other hand, everybody else's millions of dollars of investment, and asking if harming the millions of dollars of investment is proper on behalf of the guy who put in $1k.
If Zuckerberg is determined to have signed this all away, then the incorporation and all the shareholder agreements, and statements, etc. are void and fraudulent. This impacts not just Zuckerberg, but the other parties he is in business with.
It is nearly inconceivable that a judge would trash the entire corporate structure of Facebook based on this suit. Now, that said, he may sit Z down and say "I'm dumping this problem on your lap, fix it, buddy" by leaving the door open for personal fraud claims and damages to the corporation.
Regardless, in the end a judge is going to be asked if a $1,000 passive investment really should be worth billions of dollars in 6 years. The answer to that question in our country is 'no.'
Also, no way in a cold and frozen hell will DST and MS allow this guy to sit on the board and vote shares. The legal forces arrayed against him are going to be seriously, seriously formidable.
Look for a multimillion dollar settlement. Less than $100mm.