No, not the kind of money problem you or I might have. It's unlikely that he'll ever come up short at the end of the month. But he does have problems with two aspects of his wealth: his lifestyle and his financial arrangements. In the hands of a more skillful politician these wouldn't be serious problems, but in Romney's case he's been so tone deaf that they're starting to hurt him.
The first problem Romney faces is his well known extravagant lifestyle. There's nothing wrong with being wealthy, but in American society it's considered somewhat déclassé to flaunt it unless one wants to wind up like the freak show Donald Trump has become. It's certainly a drawback for a politician running for office. I can't recall ever seeing a successful politician who ran on the concept that he's richer than most people and therefore knows better. Every politician runs as a "man of the people" with varying levels of success. Romney was born into wealth and increased it substantially during his career. But that career, buying and selling companies for millions and even billions of dollars, is not something the average person can sympathize with or even envision.
There's nothing inherently upper class about being an equestrian, I live in horse country and plenty of non-1%ers have horses. They even engage in dressage. But they generally don't get $70K tax deduction (technically a passive loss carryover) for doing so. There's nothing wrong with having a large house, even a large vacation house. But having a car elevator is pushing it, and actually hiring a lobbyist to push for changes in local zoning laws is way beyond what Democrats could even hope to make up. The fact that he's engaging in this type of behavior while running for President (something he's been working on for at least the past six years) implies a kind of tone deafness that is really extraordinary for an American politician. As Michael Gerson points out,
Romney’s wealth is not ill-gotten. His problem is political. He talks about money as though engaged in a discussion with his stockbroker. So $374,000 from paid speeches is “not very much.” He is “not concerned about the very poor,” on the assumption that the safety net is enough for them. His wife “drives a couple of Cadillacs.” While not a racing enthusiast himself, Romney has “some great friends that are NASCAR team owners.”
All of these individually wouldn't matter that much, but taken together it paints a picture of someone who lives a lifestyle far beyond average (and even many wealthy) Americans. That's a problem for someone running for President at a time when the poor and middle class are told they have to sacrifice things like affordable health care and a secure retirement. By itself it's not insurmountable, but it is a drag on the campaign. It also doesn't help that Romney's tax plan (such as it is) will increase taxes on the middle class and lower then for the wealthy even if using highly unlikely assumptions in evaluating it.
Next we get to the heart of the matter, Romney's financial arrangements. These stem from the fact that he was born wealthy and increased his wealth substantially during his tenure at Bain Capital, a firm he co-founded. Bain engaged in several actions that while legal are political poison, including asset stripping, raiding of pension plans and loading up acquired companies with debt.
First things first, let's get rid of the idea that Bain (or any other company) functions as "job creators". Companies only add jobs when they have to. if they found a way to operate a company with a single employee while making their profitability goals they certainly would do so. Any job creation that occurs is despite, rather than because of, the owners requirements for financial return on the assets invested. Even Mitt Romney admits this. Bain was no different, and often quite a bit more ruthless, than other ownership groups in these areas. In fact, they pioneered the use of increasing leverage at purchased companies to guarantee a healthy return to themselves. Most people, when hearing about Bain's business practices, are very surprised to hear that Bain ensured it's initial return on an investment whether the company succeeded or not. It's another example of the "heads I win, tails you lose" attitude of Wall Street and does not play well with most voters in the fallout from the continuing financial crisis.
There are several symptoms of the kind of wealth Romney became accustomed to, the key political issue arising from this is his refusal to release more then 2 years worth of his tax returns (and incomplete release at that). It's already clear that he used offshore accounts, and while there's no proof of tax avoidance that's by far the main reason such accounts are used. There was a recent report that Italy still considers some of the transactions he made when acquiring Italian companies questionable at best. And there's the very unusual issue of having tens of millions of dollars in one's 401K account (which are limited to annual contributions in the $5K - 50K range).All of these are conditions exclusively engaged in by the very wealthy, and while I'm sure Romney was scrupulously careful to make sure that they were all legal they still stink. They stink even more when coupled with a financial reform plan that seeks to reduce the taxes of the wealthy and increase it on the poor and middle class.
The tax returns really are a millstone around Romney's neck. Every time the issue is brought up, Romney and the Republicans are forced to play defense. You really don't want to be in a situation where two words completely disrupts your campaign, and can continue doing so right up to the election.It's the first sign in a long time that the Democrats haven't completely forgotten how to play hard ball politics, and it seems to enrage Republicans. That's a big advantage since people tend to make more mistakes when they're emotional about a subject. More and more Republicans are asking Romney to release his returns, they can see where this is heading and they don't like it.
Expect to hear a lot more about these issues in the fall because, no matter what some on the right say, how one acquires a fortune and how it is handled are very legitimate political questions.