Dude: think it through. Steve Job's unprecedented :) is overwhelming evidence of his intent.
When an animal trainer gives a dog a cookie for jumping through a hoop, it's beyond question that the trainer intended the dog to jump through the hoop. Even the dog understands that. That is exactly the situation here.
In your analogy, what dog got what cookie for jumping through what hoop? From context it would seem you're saying that Schmidt recieved the email with the smiley as a "reward". It wasn't sent to him though, but to some HR person at Apple (probably the one who escalated the issue to Jobs).
When an animal trainer gives a dog a cookie for jumping through a hoop, it's beyond question that the trainer intended the dog to jump through the hoop. Even the dog understands that. That is exactly the situation here.