Well that makes no sense. If they can dominate the league as they did the first 20-30 games then explain why "they aren't that good this year".
Are you saying that the first part of the season was "luck"?
I advise that you pay him no heed. He oozes defensive pessimism; he refuses to hope that the team will win it all this spring, as this would open up the way for potential disappointment if the team loses in the playoffs.
In other words, he can simply say "I told you so" if they lose, but if they win it all, he'll bat his eyes and sheepishly smile and act as if he's the team's biggest fan.
The team deserves better than this, IMO.