I looked back at last year's tournament (using even numbered years). The very last season filled was 1990. In round 1, the 1990 teams won 95, 90, 88 & 80 games... easily the best division, Not only that, but in round 2, the two 1990 teams that made it to round 2 both made the playoffs.
The second and third to-last seasons to fill were 1984 and 1982. The division winner in 1984 won 95 games in round 1. The division winner in 1982 won 101 games in round 1 and went on to win the World Series in round 2.
The point is that a team from any division can win this tournament. It all depends on how well you draft your team.