When the Nationals were nothing more than a punchline and ESPN had to begrudgingly show their highlights, they would still mention the president's race and Teddy always losing. That was amazing at the time. It was a great gimmick and great marketing and years later they're still talking about it. Like it or not, we're still the worst franchise in baseball, at least for now. Any publicity is good publicity. The second Teddy wins a race, we're just another team that has weird things racing around its field and the hook is gone forever.
So no, Teddy isn't going to win the race the first time we clinch the playoffs, or the first postseason playoff game, or even game 7 of the World Series. Teddy will never win a race, nor should he.