John McCain’s campaign has said it was going to go negative and proved it with attacks from running mate Sarah Palin and McCain himself on Barack Obama’s patriotism. Of course, as anyone who’s been following politics for some time well knows, negative campaigning is a double edged sword. Sometimes, like with George H.W. Bush in 1988 and Harry Truman in 1948, not to mention the greatest negative ad of all time, it can work wonders. Other times, it simply signals that one candidate is far behind and wants any sort of boost in the polls, leading to negative ads that take attention away from the issues he or she is losing on. Yet there’s one other aspect of negative campaiging that can prove especially damaging to a candidate who decides to walk down that path – the risk of highlighting skeletons in one’s own closet. And that’s exactly the can of worms John McCain has opened with his newest campaign strategy.

McCain has taken the low road recently, highlighting Barack Obama’s associations with convicted developer Tony Rezko and, more importantly “domestic terrorist” Bill Ayers, now a university professor in Chicago. Obama did work in the same non-profit group as Ayers, as well as at the same university, but their relationship was never terribly close (certainly not as close as McCain’s relationship with Charles Keating). Of course, the Obama campaign has hit back with the above video highlighting McCain’s central role in the Lincoln Savings & Loan scandal that ended up costing American taxpayers billions of dollars in the late 1980s.

As FiveThirtyEight.com recently pointed out, negative campaigning works well in one particular scenario: if the negative information is coming from something that has recently surfaced in the news. For instance, let’s say that Bill Ayers blew up a building tomorrow and caused hundreds of deaths. Suddenly, to question Obama’s assocations with the man would be extremely newsworthy and timely. Yet Ayers hasn’t done anything of that nature in over 35 years. To bring him up is certainly appropriate, considering his past, but the allegations (which are rather ridiculous considering that Obama wasn’t even 10 years old when Ayers was at his craziest) aren’t exactly damning. McCain’s associations with Keating, on the other hand, are a completely different story.

The Keating Five scandal plays directly into the current economic crisis by serving as a prime example of John McCain’s philosophy on government regulation of the economy (or lack thereof). It shows McCain as a politician more concerned with kickbacks and contributions than with the well-being of American taxpayers. In a year when people are going to vote with their pocketbooks with an eye on their 401k, to see a candidate out there who played a central role in the last huge American financial crisis trumpeting his deregulatory and maverick credentials isn’t exactly going to sit well.

In the end, you can’t fault John McCain for doing anything he can to win an election (it wouldn’t be the first time he did whatever it took to get ahead). But you have to think that this latest strategy, considering his past and the current economic situation, is doomed to backfire. And backfire spectacularly.

For me, the most ironic part is the McCain-Palin campaign’s attempt to portray Obama as someone who’s “palling around with terrorists” when McCain himself used to get free trips to the Bahamas from Charles Keating, a man who could be considered a domestic terrorist for stealing the savings of over 20,000 American citizens.