As a Will Rogers Democrat , I’ve been watching with delight as Donald Trump states, re-states, and then doubles-down on statements that seem almost perfectly designed to offend the median voter and put other Republican presidential hopefuls—now a not insignificant percentage of the entire party—in uncomfortable positions. The whole thing is almost too good to be true.
Then in the fading wakefulness of last evening, as the brain starts making random connections that are both crazy and creative, it hit me in a flash: what if it is too good to be true?! 
That is, what if Trump is pursuing the Stephen Colbert strategy of setting himself up as a parody of the looney right, and simply seeing how far he can go? Consider the following seven characteristics that point in this direction.
1. As has been pointed out in numerous forums , for most of his life Trump has been not only a Democrat, but as Dana Milbank has pointed out, a fairly progressive Democrat at that.
2. His “born again Republican” schtick does not have any obvious motivation—nothing equivalent to Ronald Reagan’s battles with Communist-influenced unions in Hollywood—and he flipped almost immediately into an extreme position.
3. His positions, first as a “birther” and now as a combination of an anti-immigrant know-nothing, Putinesque Great Dictator and Green Lantern seem almost optimally designed to embarrass the GOP by focusing attention on the looniest of the loony ideas floating therein. To date he is completely ignoring Republican leadership appeals to stop the madness.
4. What, exactly, is “Trumpism”?: it seems to change by the day but in addition to overt racism, includes such howlers as secret plans to impose his will on a country holding $1.2-trillion in US debt. In contrast, the libertarianism—if that’s what it still is—of Rand Paul may seem a bit fringe, but at least it is a coherent ideology with a long political and intellectual history.
5. No one gives Trump even a remote chance of winning a general election, however successful he might be in primary elections in small states. But he could certainly thoroughly disrupt those already problematic Republican primary debates.
6. Trump may or may not be threatening to run a Ross-Perot-like third-party candidacy if—which is to say, when—he doesn’t get the GOP nomination. This would almost certainly throw the electoral votes of Michigan, Ohio, Pennsylvania, Florida, Virginia and possibly North Carolina to the Democrats, at which point we could save some time and effort by skipping the election altogether and just appointing Hillary.
7. Like Colbert, Trump is a television entertainer: let us not forget that.
Trump, bluster notwithstanding, seems to be paying at least some price for these antics, though of course if he is worth any significant fraction of what he claims, he is nowhere near the poverty level, and in the meantime it appears that he will be providing lucrative employment for legions of contract lawyers.
But whether or not it is an act, this is going to be a tough tiger to dismount. And if Trump is, in fact, doing this—with thus far devastating effectiveness—as a favor to Hillary Clinton and the Democratic Party, probably the best comparison is not to Colbert, but to the undercover but nonetheless heroic and self-sacrificing Severus Snape. Hey, they already appear to share the same hair stylist!
9 Dec 2015: For the update, five months out, see https://asecondmouse.wordpress.com/2015/12/10/seven-updated-observations-on-trump/
1. “I am not a member of any organized political party. I am a Democrat.”
Read more at http://www.brainyquote.com/quotes/authors/w/will_rogers_2.html#6z1ffTDwfSkujHaa.99
2. The conservative Washington Times—I’m not a regular reader, and found this only as the result of Google—is apparently also having some of these same doubts.
3. Google “donald trump democratic donations” for a long list of essays to this effect.
4. To say nothing of the price his employees must be paying: the thoroughly loathed “Trump Winery” is just a few miles from here and I’m certain few if any of the people working there expected to be signing on for this sort of thing.
5. Though this is quite a recent development, as Chris Cillizza pointed out just three weeks ago.