By letting more films compete for the top trophy, the academy is merely following where others have led. Call it "cultural inflation": a growing number of opportunities for the less deserving to get a taste of ultimate victory, as part of a growing aversion to disappointing anyone.
For children, this manifests itself in giving every member of the soccer team a trophy regardless of how well he or she or the team performs. And just as some have concluded that such an exercise in building self-esteem may teach an unrealistic lesson about real-world winners and losers, so may cultural inflation mislead us about what is good or bad, and even change the standard.
Yet cultural inflation is not only a function of money. It is equally a function of modern democracy. Put simply, people in a democratic society such as ours don't understand why they can't always get what they want. The culture obliges by pandering, which is what the Oscars are doing by expanding the field. It is a form of cultural demagoguery that doesn't dare disappoint people -- the adult equivalent of those children's soccer trophies. In effect, we live in a "panderocracy."
Basically, Gabler fears that "the motion picture academy may risk tarnishing the Oscar, especially if votes are split and an outlier wins." Of course, he needn't worry because under the five-nominee format, we've already been blighted by such Best Picture winners as The English Patient, Titanic, and above all (or should that be below all?), Crash.
But let's pretend that the Academy represents an entity that generates reputable critical consensus -- it's in a position to refine or redefine the parameters of quality pictures by becoming a force of positivism rather than negationist. It's a sign of greater aesthetic maturity to like a lot of things than to like very few. To put the matter another way, our tastes should be defined by what we like, as opposed to what we don't like. (For example, I don't like most performances on SYTYCD, because my taste in dance is still pretty immature. On the other hand, I'm liable to bump universally reviled R&B or African folk music at any given time, so I'd consider my taste in music to be relatively mature.)
Likewise, then, an expanded shortlist of Best Picture nominees isn't a sign of coarsening cultural values, it's a chance for films that don't fit the prescribed Oscar-bait formula (a dour drama that grapples facilely with middlebrow ideas) to get time in the sun, as I mentioned above about Pixar films. Furthermore, any opportunity for people to reassess the artistic validity of different genres is an overall win, in my book, and the Oscars is as wide a venue as you can get in this regard.
And a digression that people who aren't interested in sports can safely ignore: Gabler also mentions baseball as one analogous example to the Academy's lowered standards. It used to be that "major league baseball teams had to win their league championship over the course of a long season to qualify for the World Series." Leaving aside the fact that teams still have to win their leagues to move onto the World Series, he overstates how much the expanded playoffs have diluted the quality of World Series teams. Since the institution of the wild card and the divisional round, the team with the better record has won its series 54% of the time. Hardly better than a tossup! Why, in the good old days, when baseball had only one round of playoffs before the World Series, the better team won a mighty 60% of the time! This 6% difference is stark and outrageous! (I computed both percentages -- based on Baseball-Reference.com -- in a raw, dirty way </sexy stats talk>. A more thorough approach would consider Pythagorean winning percentage instead of actual winning percentage, but I'm not an actual SABR nerd.)
Not only is his baseball example wrong, but in the context of the other sports he mentions (college hoops and football, the NFL), the MLB remains the most exclusivist league in terms of allowing teams into post-season play (8 per year out of 30 teams).