First, he thinks that it would be an unfair advantage:
DC is at the very heart of the country’s power structure. It is the part-time residence of every one of our federal elected officials. While voters may indeed lack proper representation, giving DC the added clout of two Senators and a number of representatives, plus all the other perks that come from statehood, would vastly tip the scales in DC’s favor.The problem with this theory is that the interests of Members of Congress as part-time and temporary residents of Congress often clash with the interests of the people who actually live in the District. So if anything, permanent District residents are bound to be in worse shape, not better shape, than residents of Alaska or North Dakota if they want to govern themselves without Federal government influence. This is easy to see, since the District is not currently (nor has it as far as I know ever been) a paradise overflowing with government spending or any other clout-derived benefits.
Second, Kain doesn't like the idea of a city-state:
[I]f DC can be its own state based solely off of the size of its population, why shouldn’t other cities also become states? New York City has far more people than DC. Perhaps each of the Burroughs could become a state.Well -- why not? Makes as much sense as having large mostly empty states, to me. Obviously, for various historical reasons, the fifty states are what they are -- but there's no underlying logic or sense to them. After all, prior to 1960 there were no states remotely like Alaska or Hawaii, but those have worked out just fine. There's little question in my mind that current residents of the District think of themselves as citizens of a politically separate jurisdiction, certainly more so than people in "North Dakota" presumably thought prior to their statehood. Thinking that a city can't be a state is just prejudice, not argument.
Third, Kain believes that there's a principle at stake here:
Then again, the representative system in this country was never meant to be entirely based on population. As with every other aspect of our government, our electoral system acts as a set of checks and balances. That may be frustrating, but it is what it is...This is why we have two bodies in Congress – the House and the Senate. Each state gets equal representation in the Senate, but not in the House. Granting DC statehood makes sense if we’re going to base our representative structure on population alone, but that’s not how this country works, and that isn’t likely to change any time soon.Here's the thing about representation, something that is I think fairly little known: political representation is a really, really new idea, historically speaking. For example, you won't find it in Shakespeare, because it hadn't really been invented yet. By 1776 it was an established and recognized fact in England, but there was very little systematic thought about it yet (Burke's famous speech to the Electors of Bristol was in November, 1774).. So in large part, the Framers were making it up as they went along; Madison's insights into democracy and representation were really very new, really original. It wouldn't be surprising at all if their understanding of representation was not fully mature. Folks back then thought that women didn't need to vote, and they had ideas about representation to support that notion, but they got that wrong -- and they got representation of arbitrary pieces of land wrong, too, to the extent they believed in it. Anyway, as we know, the House/Senate distinction wasn't made on principle; it was a compromise forced on everyone by political necessity. So while we're stuck with it, we don't have to embrace it as a virtue or a founding principle.
The truth is that the American political system has rejected representation of places, not people, at every other stage of the political process, ever since the "one person, one vote" Court decisions of the early 1960s. And as far as I can tell, everyone is pretty much OK with that in virtually every context. No one is arguing that states would be better off -- more democratic -- if they had upper chambers apportioned by counties, not population. The Senate is an unfortunate anachronism, one that we're stuck with, but not one that can be justified with any recognizably contemporary democratic theory.
(And don't even think about trying the old Reagan saw about the states creating the Federal government and not the other way around. Perhaps 13 states could make that argument (against 37 the other way), but even there a map a 1770 Virginia isn't going to remind anyone too much of 2010 Virginia...and the Constitution is authored by We the People, not We the States).
None of this demands that representation of the citizens of the District can only be achieved through statehood, as opposed to the Maryland option. But Kain's arguments against statehood in principle strike me as wrong or misguided. In reality, as with all statehood decisions, it comes down to political expediency, but in my view supporters have nothing to be embarrassed on the merits, certainly not the merits on democratic grounds, of DC statehood.