"Mitt Romney looks like the guy who comes to lay you off" - Mike Huckabee.
A lot of his problems stemmed from that 2009 article about how to handle Detroit. What he described in the article was a structured bankruptcy backed with US gov't money to hold them over. However the headline conveyed the equivalent of DROP DEAD NEW YORK!!! from Gerald Ford's days.
I spent years splitting hairs on this point to defend Romney between 2009 and 2015, but at the end of the day it was a mess he could have easily avoided just by keeping his mouth shut.
Romney also stepped in it with his book, similar to Jeb Bush on immigration, but on health care. What this illustrates is the danger of political books, and the fact they take a few months to get out into circulation and politics moves much faster. Just as Jeb was embarrassed by his book claiming to support only a path to legal status after Rubio had been working the grounds on a 2013 compromise that included a path to citizenship.
Romney contrasted Obamacare from his MA healthcare plan on the basis that Obamacare had a public option, and Romneycare did not. This was the case when the book was composed, but not by the time it hit the shelves. The public option had been dropped making Obamacare hard to differentiate from Romneycare Oops, back to the drawing board. Romney then failed to come up with a consistent narrative after that point. His best bet was a Federalist approach of letting states design their own plans and giving them the money to help facilitate that.
But beyond all of that, it would have been rather difficult for Romney to overcome his Bain Capital days in any case. Too many displaced workers and too many video clips that wrote themselves.
Were it not for social issues, lingering Gay Marriage opposition and the War on Coal narrative, Romney would have done even worse in the Midwest.
Ironcially though in 2008 primaries pundits were calling Mitt the strongest Republican candidate for states like Michigan and the Midwest in general. They believed he would be weaker in the south though(In 2012 it turned out to be the opposite)
It was right after the Michigan Primary when Romney easily won and Chris Matthews was talking about how Romney might be there best candidate for that region
That was almost a year before the article "Let Detroit Go Bankrupt" was published.
Romney ran on a proposal to boost investment in energy and transportation Technology, which McCain ever the ardent fiscal conservative when it comes to subsidies, lambasted as a bailout. Romney defeated McCain in Michigan and it revived his sputtering campaign. Romney had also made big issues about currency manipulation (which he would bring up again in 2012 but failed to make it stick), bad trade deals in some of the later debates and of course immigration.
Also no one had gone after Romney on Bain Capital yet and the theory was since he had been able to win MA GOV in 2002 in spite of it being hammered on in 1994 by Ted Kennedy, he would be fine. Especially if his opponent was Hillary Clinton and thus all Romney would have to do is mention NAFTA.
Also Romney didn't have to run away from health care in 2008, but could embrace it and use it against Clinton who had failed to deliver once before, saying he could "get it done". Healthcare was often listed as one of the top 3 or 4 issues and has a salient appeal in the Midwest that people have long underestimated and is a part of the reason why Obama defeated Romney so badly in the Midwest in 2012.
In the 2012 primaries, Rick Santorum was backed into a corner at one point after attacking Romney on health care because he had endorsed Romney in 2008 just two years after signing the bill. His response was, "well that was against John McCain".
Of course, Hillary Clinton was not the Democrat nominee in 2008. Obama had a lot of things going for him, not just because he was from the Midwest, but also higher minority enthusiasm and turnout (made Indiana possible), not being party to the votes and proposals in the 1990's, his support for a public option, more consistent anti-war stance and pledge to crackdown on employers of illegal aliens.
Add to this anger at the Bush administration over the economy and the war. I can see a path for Romney in 2008 against Clinton, but it is hard to see that against Obama.
