No, I am not saying this as a disgruntled Yankees fan. This is merely an objective perspective.
Is it fair that the Yankees, a team on pace to win 102 games, is virtually guaranteed to be in the do-or-die wild card game while the Indians (on pace for 91 wins) are guaranteed at least three additional games?
Yes, a team should be good enough to win its division, which the Yankees are clearly not, which is why they are just 5-8 against Boston this year. But what about counteracting teams that are not as good as the Yankees record-wise and are also benefiting magnanimously from a division in the AL Central where its foes own a combined 179-286 (.384) record?
Of course, the problem is also prevalent in the NL. The Brewers and Braves both own better records than the Dodgers and Diamondbacks. Either Arizona or the Dodgers will win the NL West, but could also end up having a lesser regular season resume than the aforementioned Brew Crew or Braves, and yet have a better security blanket and much lesser margin for error in October.
Now, a one-game match between the Brewers and Braves is certainly a compelling thought. The two clubs have never encountered each other in the postseason. Alas, this is about fairness, not necessarily what fans want.
The same argument applies. While the two may not be division champions (though the Brewers trail the Cubs by just two games, and the Braves trail the Phillies by just one), they will likely have better records than the eventual NL West champion.
In an era where leagues have gone out of their way to achieve parity, it seems that there is still headway to be made as far as a truly palpable playoff system goes.
The problem is that changes to playoff formatting have often taken a long time. From the first modern World Series in 1903-1968, it was only the World Series, which featured the two teams with the best records. Home field advantage alternated annually.
From 1969-1993 (there was no postseason in 1994 as a result of the strike), there was the additional League Championship Series (ALCS and NLCS), with the exception of 1981.
In 1995, the Wild Card was introduced, and the League Division Series became a permanent fixture.
In 2012, an additional Wild Card slot was added, and now we have the one-game playoff, or a play-in game, if you will.
So as much as many want the system to be resolved, it could be a while. At the earliest, it could take place in December 2021, when the current CBA expires.