Board Thread:Fun and Games/@comment-26815144-20161007110349/@comment-25356210-20161007145821

A reply to Legoarmy:

Sauron probably did enlist Easterlings to attack Dale. However, simply put, it's speculated the Blue Wizards foiled this plan.

Smaug, however, probably would not listen to Sauron. It's fairly certain only Morgoth himself controlled the dragons.

As for your second point... Easterlings never took Erebor or Dale.

As you can see, no stupid mistakes where made, but rather Sauron was inconvenienced.