http://warlight.net/MultiPlayer?GameID=4656454 Why do you think Teddy wins despite his lower income?

Becuase he is preventing the enemy from getting the bonus?

Teddy had a safe bonus that wasn't threatened until much later. Summer spent troops doing things that were not ideal, like sitting in Africa not being used, or attacking Brazil and then sitting for a turn.

The biggest thing, though, was that Teddy could force moves (defense of Russia) and therefore control his opponents options. If Summer had a safe bonus, then Teddy would have lost that ability and would have had a much harder time predicting his opponent.