The two sports aren't really all that similar.
Baseball is disproportionately impacted by luck.
There's a reason why the last ~50 years you've pretty much only seen Iowa, Okie State, Penn State, Iowa State AZ St, a year of Minny, OSU in there and...that's going back to Bobby Kennedy's assassination.
Lets take the best Wrestler on Penn State and the best player on the Yankees(and best RHH Hitter arguably ever). What are the chances Mesenbrink is perfectly healthy and just terrible in the post-season or at least about 75% of what he is in the regular season? They're pretty low, right?
Yet with Judge... they're not so low. It's been the last 5 post-seasons.
So... I get what you're saying, things can change, but the best team ALMOST always wins in Wrestling. The Best team in Baseball... the most TALENTED team, most dominant team... they usually don't win. You can hit a ball 110 MPH off the bat and it gets caught or you can hit a ball 19 MPH off the bat like the '01 World Series when Luis Gonzalez singled on a blooper to CF off the greatest closer of all-time.
Baseball dynasties are incredibly rare. Wrestling Dynasties are not.
Also, Wrestling is not really a team game. It's an individual sport in which you just add up all the individual scores. So... not the best analogy.