In asking this question lets ask another one that is related. Does it matter whether the person is a self-made billionaire or if the wealth was inherited? And here is still another question. Does it matter whether these donors were activist in politics before the Citizens United decision? In other words, if there are newbie donors among the group are they motivated to give to their preferred candidate for different reasons?
Now a few asides before getting to these questions. In the old days there was machine politics. There was the notion of a smoke filled room where the real decisions were made. Jimmy Carter has gotten some attention recently for calling the U.S. an oligarchy. Bernie Sanders has been saying the same thing for quite a while. Sanders has a Norman Rockwell painting of a town meeting featured in that piece. Not that it didn't happen, but it is misleading as a caricature of our past politics. Everyone knows from the history books the name of Boss Tweed and Tammany Hall. That stuff didn't end in the 19th century. When I was a grad student at Northwestern (starting in 1976) the first Mayor Daley was still running Chicago, and his machine was still functioning strong, though it did start to break down after Daley passed away and his successor Bilandic didn't get the plows out during the massive snowstorm in 1979.
There is also the issue of dynastic families and national politics. This goes far back, at least to John Adams and his son John Quincy Adams. (Whether there were family dynasties present in colonial politics, I do not know.) Keeping it in the family is a different way to concentrate power.
Is it possible that power in politics has always been concentrated in America and that the only thing which is new is that the locus of this concentration has changed?
This is not to defend concentration of power as a good thing, but simply to observe that we're a republic not a direct democracy. Further, to the extent that our interests and views are heterogeneous and our influence individually essentially nil, the nature of the politics itself encourages special interests with some power to express that in a way. Consequently, concentration of power is something that an economic analysis of politics would predict. One should not expect it can be eradicated entirely, but there may be good and bad ways of doing this. In my view, that is a better way to frame the issue around Citizen's United than to hearken back to a Norman Rockwell ideal, one which doesn't give a good picture of how things really were.
Now back to the puzzling. I recently read a piece by Malcolm Gladwell that he wrote five years ago about how entrepreneurs really make their money. It is an interesting read in itself because it challenges the popular notion that it is high risk tolerance, "animal spirits" if you will, which distinguishes the entrepreneur from the rest of the population. In contrast to the popular view, Gladwell argues instead that the entrepreneur is highly risk averse, in constant search for the sure thing, and able to pounce on it when the sure thing has been identified. This can happen if (a) the rest of us are slow to see the sure thing because we don't spend the time looking for it and (b) even if we spotted it we wouldn't pounce because we don't trust ourselves and think there is more risk than there actually is.
The opposite of the Gladwell story can be found in Daniel Kahneman's book Thinking Fast and Slow, in the part of the book where he takes on the arguments of Jim Collins made in Good to Great. Kahneman says Collins cherry picked winners after the fact. Before the fact, the great success story in the making is impossible to identify. Hence, much of the entrepreneur's success should be attributed to having a run of good luck.
Keeping both of these views in mind, let's use as example the candidacy of Rick Perry, which from my outside perch illustrates the puzzle. Perry has gotten some very big contributions, yet he has to be considered a dark horse in this race. Here are some possible ways to explain the large contributions that Perry has received.
(1) Perry has improved dramatically as a candidate. He is much better than he was four years ago. It's just that the public doesn't know this yet. (This explanation is consistent with Gladwell's depiction of the entrepreneur.)
(2) There is a big upside to becoming President. For these donors' making a campaign contribution is like buying a lottery ticket for the rest of us. Donors look at the upside, not at the expected reward. (This explanation is not consistent with Gladwell. It may not even be consistent with Kahneman, who surely would argue that the probability assessment of success matters. This explanation is consistent with what I said above about frivolous reasons and yacht racing.)
(3) Running for President is a kind of personal marketing that can produce reward apart from winning the election. The donors expected to do further business with Perry after the election and Perry's value in those transactions gets enhanced by his running for President now. (This seems much more likely to me than the first explanation and is also consistent with Gladwell.)
(4) This is simply returning a favor to Perry, who was loyal to the donors in the past. Perry solicited the contribution and they responded to the solicitation with generous contributions.
(5) This is the first Presidential election since Citizen's United where there isn't an incumbent President running. Lacking prior experience the donors don't completely understand what makes sense here. So they are willing to try things to learn from the experience.
(6) Contributors are more interested in having leverage with their candidate than they are in backing a likely winner. Jeb Bush, who measured by contributions until now is clearly the front runner, already has such a large war chest that he is less malleable to influence by the marginal large donor, especially those who haven't had a prior relationship with him.
It may be possible to extend the list. It is sufficient for my purposes and what I have to say next. The dynamics of the race may be influenced by the presence of the large donors in ways where it wasn't in the past. In particular, a poor early showing need not be cause to drop out of the race, because overall contributions may be ample to continue. Dark horse candidates like Perry will need to take risks to try to vault the field. Negative campaigning is likely as a way to do that. The various hopefuls will beat each other up. Even if Donald Trump fades, the type of behavior he exemplifies is apt to continue.
In other words, the large donors who are not backing one of the front runners seem to be playing a Prisoner's Dilemma and it is a puzzle why they would opt into such a game rather than sit it out. This recent piece makes the same point about the Republican's playing a Prisoner's Dilemma.
In fact, though, Citizens United has created a new dynamic within the Republican Party. Call it the politics of plutocratic patrons, and at the moment it is causing the GOP to eat itself alive.
But it argues that the wealthy donors are winners here, because they've become king makers. I think that claim is wrong. Most of them will be losers in that their preferred candidate won't get the nomination. And it may be in aggregate that the Republican field gets twice as much in contributions as the Democrats, yet the Republicans still don't win the election. In that case, it seems to me, these donors will themselves come to conclude they are losers. The question, then, is why they don't seem to have the forethought now to project that possibility. Alas, it may be impossible to really study this because the donors likely wouldn't allow social science researchers to get close enough to learn deeply about donor motivation.
What are the implications of this sort of thinking? First, in considering Citizen's United the pernicious impact that so many care about may be more prominent in Congressional races and State races. Those races are less likely to produce a variety of donors who compete with one another via backing different candidates. Second, using political campaigns as self-promotion for outside of politics is detrimental to the process. It is something to discourage and provides an argument for limiting campaign contributions. Third, it may be that this election cycle is unique and that for the race in 2020 the donors figure out how to coordinate among themselves so as to avoid the Prisoner's Dilemma, even if such coordination runs counter to the libertarian philosophy that so many of them seem to hold. However, it seems possible to me that enough of these donors are pig headed and that what we'll actually see four years down the road is a replay of what we are seeing now.
This gets me to the last point. Some people treat personal wealth as a kind of badge, with the uber rich better than the rest of us with their wealth offering proof of that. This sort of mindless spending in support of unlikely candidates is evidence to the contrary and supports the position that these folks should pay more in taxes. Or at the very least they should stop throwing stones by criticizing government spending. The glass house they live in is very large.