Hard to say based on what you put down. other than the soft handshake which may be a code word for "gay" and thus perhaps a sexual orientation discrimination case, if they don't think he had a sense of urgency they can fire him. He should consult with an employment lawyer in Chicago.
The short answer is probably yes. Depends on if the person was drinking in the bar and was intoxicated. Also, depending if you were on public property like a sidewalk or on private property, you may sue the property owner. Call a personal injury lawyer.
Why not get a prenuptial? You can also keep the money in a separate bank account and never co-mingle the money but it can be challenged and then it would be up to a Judge to decide if the money was co-mingled or not. The prenuptial is the way to go.