Courts do grant damages for loss of profit or opportunity....

Courts do grant damages for loss of profit or opportunity. Usually the main issue is proving that there was a clear opportunity available and, if you had of taken the opportunity, that a "more probable than not" profit would have been made. This is a causation test, and you are right in that it can normally be hard to prove for commercial opportunities a plaintiff may have missed. However, Sheehy is on pretty strong ground on this issue, as there's no doubt of the probable profit, as all he has to do is point to the SP history.

However, the other thing he would have to establish is as a question of fact that he was "more likely than not" to have been able to have picked the top AND to have sold all of his shares. He needs to lead actual evidence, not just that he "could of", but that he "would of". Relevant evidence might be what he did with any options that were actually granted. While I think some damages for lost opportunity may be granted, I do think that it would certainly be discounted from the SP high. Courts know that hindsight is 20/20 and are unlikely to accept that it was probable that he "would have" been picked the market top and sold all of his holdings. Perhaps the court might take an average SP over a certain period, assuming that he wins.

My opinion only and do seek independent advice.