The first “October surprise” didn’t take very long to come out as the NY Times released an article dissecting and speculating about three pages of Donald Trump’s 1995 tax returns that were leaked to them last month. While Hillary Clinton supporters are tripping all over themselves to scold Trump for possibly not paying certain taxes, including the federal income tax, for up to 18 years, Trump supporters are scampering about saying that he’s brilliant and pointing to this as proof that he’s the right guy to get all of this stuff cleaned up.

Meanwhile, there’s a chance that Trump is sitting back and watching the carnage as his latest plan unfolds before us all.

The snap response to this concept is that there’s no way he would do it. Why would he do damage to his own chances by leaking information that could hurt him in the eyes of voters? To answer that question, we must first check our premises. First, does this really damage his chances? If it does, could doing so mitigate worse damage that he might be expecting? If it doesn’t hurt his chances, is there a potential gain that can come from all of this?

Let’s start from the beginning. Does it hurt his chances? With his core voters, absolutely not. Nothing could hurt his chances with them. Nothing. What about his reluctant supporters? Are people like Mark Levin and Ted Cruz going to yank down their endorsements? Will those in the “but, Hillary” crowd switch votes? No. How about the all-important undecided voters? Some of them might lean away from him for now, but those who haven’t made a decision yet likely aren’t going to finalize their choice for Hillary now just because something that has been speculated about for a year has inched closer to being proven factual.

Now, let’s give it the benefit of the doubt and say that it does some real damage to his standing with voters. Could this be mitigating future damage? If he plans on releasing his returns in the future or fears that they will be released by someone outside of his sphere of influence, then preparing the masses to find out about his tax practices would be a prudent move. By bringing it partially into the news cycle, it desensitizes the masses for a future blow if his taxes are released and show the same basic trend of tax avoidance. Of all the scenarios, I see this as the least likely, but again I also don’t believe this leak does lasting damage to his chances.

If it doesn’t hurt his chances, why would he do it? Could it be that he has more damaging items in his tax returns that he really doesn’t want people to see? If that were the case, then leaking these parts of his tax returns now gives everyone a red herring to chomp on as he coasts into election day without releasing his full returns. The media will peck at him. Team Clinton will challenge him. Pundits will speculate. At the end of the day, most voters will believe that he simply doesn’t want to be embarrassed by the combination of huge losses on paper and his practices of avoiding paying taxes through legal loopholes. Speculation about ties with Russia, a complete lack of charity, investments in China, or major loans from foreign banks will all fall to the wayside.

Could he pull it off? Of course. Those who believe that he’s just not that clever didn’t notice the he was the likely leak of the John Barron “embarrassment” or Melania’s nude photos or any of a slew of “damaging” events that have kept him in the spotlight without allowing media time to breath. Remember, his “good brain” doesn’t work like most people’s. He can suffer embarrassment like a champ. This election cycle has proven that he has no shame and fears no bad press. His minions have been programmed to turn any lemons he serves into lemonade while the media has made undecided voters so overwhelmed with negative stories that they no longer feel shock when Trump’s name is attached.

The other end of this conspiracy theory is just as valid as any of the rest of it. Is he trying to lose? Is the Trump Media Empire more than just a consolation prize? If it’s his one and only goal, then all of his actions for the last two years (or longer) suddenly make perfect sense.

I’m not a betting man, but if I were, I’d take 50/50 odds that he is behind the leak. Why? Because the pages that were leaked were no more accessible than any other pages of his returns. Someone wanting to damage Trump who was inside the organization could have just as easily pulled a full-Snowden rather than this conspicuous nibble.