Sometimes it's just that little bit more ... " it looks like he was close to his goal when he ran into trouble." that gets you. I call it the, "I know I can make it to the next gas station." mind - that becomes a manly challenge and right of passage as a teenager. Unfortunately, in a kayak, there is often no pulling over to the side of the road to get a few hours of sleep before continuing on.
Been years since it's happened to me of course, but I can clearly recall a trip from California where I passed through La Pine on the way to Bend, just sure I wouldn't run out of gas (like there was some prize for arriving with the lowest gas tank level). I just made it, but had I figured wrong, it would have only meant some time on the side of the road and a little embarrassment, not completely exhausted, offshore, with a storm bearing down.
Leaving at 9PM at night is a head-scratcher. Maybe he was trying to use some tide/current action and has to meet that schedule.