Ken, I'm a little confused by your diagram ...
Picturing the harbor in Chicago, if you were outside the breakwater headed in on a starboard tack, that would make the wind out of the north, right? So if the other boat was on a reach headed into the harbor would that also put him on a starboard reach? That would put you on a crossing path with both of you on starboard (I'm not questioning your judgement but when you know you are on starboard and the other boat is crossing, it is easy to assume the other is on port). If this is the scenerio, you still are stand-on because you are leeward. The ex-power boater factor may be in play also because if you both were under power and the other boat was approaching from your stbd side, the other boat would be stand-on.(Does the diagram show the gap in the breakwater and the other boat heading out or are you already inside with the other boat entering and the wind is actually from the southwest? That's why I am confused a bit ... you seem to imply that both of you are headed inside. If the diagram shows both of your boats, then even the under-power situation puts you as stand-on so the other guy is still messed-up).We actually had a poster in here recently who thought that starboard tack meant that the boat was heeled to starboard. People can get confused easily. Regardless, I would have been shaken up myself and upset with somebody who needlessly caused an un-necessary confrontation on a pleasant day. The world is full of all types!BTW, are you a city dweller or suburbanite?