You know its true and I hadn't considered it that way.
In fact in Star Trek 6 if it wasn't for the patch on Kirk's back and the chameloid it wouldn't have been good for Kirk. But I guess he knew Spock would always find a way to catch him.
Well its like what Kirk said in Trek 5 "I have always known I would die alone"
He has always known that his crew and good friends would work together with him to the end.
In Generations he did technically die alone even though Picard was with him. Kirk's crew and his Enterprise was gone. He was alone.