I think we are interpreting the English language differently. But I'm not going to argue about it. In the scheme of things it means nothing. How much Rob wins is not my concern. How much I win is.
But I think your statement is fundamentally incorrect. Rob has gone home without winning. He has had losing sessions. By your statement he could not leave unless he won his $2,500.
I wonder how many times Rob did win exactly $2,500? I'm going to guess he probably never did. I'm going to guess he met his win goals with wins that ranged from $2,501 up to $97,000 when he won the $25 royal at Bellagio.