In recent history, two candidates from Massachusetts ran for president. Ironically, both ran against members of the Bush family. The Obama campaign is using these as its model for running against a third candidate from Massachusetts, Mitt Romney.
In 1988, George H. W. Bush ran against Michael Dukakis who was the current governor of Massachusetts. It was an open election (no incumbent) but Bush ran as a third term of the Reagan administration.
Dukakas won the primary largely on the basis of the "Massachusetts Miracle" meaning his state's economic performance. Unfortunately, this collapsed between the end of the primaries and the Democratic National Convention, robbing Dukakis of his strongest point.
Bush ran a campaign emphasizing that Dukakis did not share the values of regular Americans. Two examples where requiring school children to say the Pledge of Allegiance daily and early parole for violent criminals. They gave Willie Horton as an example. Horton was given early parole and used it to rape and kill someone. They also ran ads attacking Dukakis on the water quality of Massachusetts Bay which the EPA had rated poor. Finally, Bush suggested that Dukakis was weak on defense.
Dukakis's campaign never really developed a coherent message for why he should be elected and the candidate made several missteps. One was appearing in a tank to try to appear stronger. This image was so laughable that it was still a punchline on a Futurama episode 14 years later. Dukakis stumbled when asked if he would parole someone who had raped his wife. And the Massachusetts Miracle turned into the Massachusetts Nightmare (ironically, one of Romney's qualifications is that he cleaned up the budgetary mess that Dukakis left behind).
The Bush/Dukakis campaign figured prominently in the book "What's the Matter With Kansas?" which held that Republicans exploited wedge issues such as the Pledge of Allegiance to entice voters into voting against their economic interests (meaning Democrats).
In 2004, George W. Bush ran against John Kerry. This time, Bush was the incumbent. Kerry won the primaries on the basis of his military service in Viet Nam. His message was that we needed a war hero in the White House while the country was at war.
As with Dukakis, Kerry's biggest qualification blew up in his face when it came out that his war service had only been for three months and he was better known for being a war protestor.
The Bush campaign attacked Kerry as being a rich, out-of-touch liberal. They ran ads from his testimony before Congress where he accused everyone stationed in Viet Nam of committing horrific war crimes every day. Kerry came close to winning an Electoral College victory but lost the popular vote by a decisive margin.
Considering the state of the economy, the Obama campaign can be seen as using wedge issues to get voters to vote against their economic interests. At the least it can be said that Obama is not running on his record. His campaign is attacking Romney as a rich and out-of-touch and has tried to turn one of his strongest points, his time at Bain Capital, against him.
How successful will this strategy be, even if it is based on two winning campaigns? There are significant differences between the present election and the ones in 1988 and 2004.
First, the Bushes attacked their opponents as Massachusetts Tax-and-Spend Liberals. This formulation was invented by Ronald Reagan and was so successful that the 2008 candidates insisted that they were "progressive" rather than "liberal". Obama is trying to attack Romney as the most conservative person to ever run for president. It is hard to believe that voters will believe that Massachusetts would elect such a man. The Obama campaign originally planned to discredit Romney's term as governor but only ran one add early in the campaign (which fact-checkers tore apart). The dissonance between "conservative" and "governor of Massachusetts" may be why they backed off from these attacks. It is best not to remind voters of his term as governor.
Both Dukakis and Kerry had the issue that they won the primaries on turned against them. This will not be the case with Romey. Newt Gingrich started attacking Bane early in the primaries and Romney won anyway. By election day voters will be sick of hearing about Bane.
Romney is harder to attack as being an out-of-touch rich guy than Kerry was. Kerry was the son of an ambassador and grew up as a member of the rich and powerful elite (although his family's wealth was at the low end). During his college days he hobnobbed with the Kennedys He eventually married one of the world's wealthiest women who, in turn, inherited her considerable wealth.
Romney was not born rich. His father worked his way up the corporate ladder and the family did not have any real money until Mitt was in high school. During his time as a missionary in France he was living on a meager allowance equivalent to $7,000/year in today's money. While Romney is quite rich, he earned his wealth himself. By the time his father died, Romney's personal fortune was so great that he used his father's inheritance to fund a scholarship fund.
The biggest problem for the Obama campaign is that the background is different today than in the other election. In 1988, there were no overriding issues. The country was at peace and the economy was doing well. In 2004, Bush still had a store of good-will left from his response to the 9/11 attacks. The insurgency in Iraq was just starting and most people counted the war in Afghanistan as being won.
In contrast, Obama has a poor economy to answer for and his biggest aaccomplishment, Obamacare, is a divisive issue.
Obama has been counting on the "likability" factor. While his overall approval rating is down as is his handling of the economy, most voters still say that they find him more likable. Romney has a good chance of turning this around. The Obama people have been emphasizing how "strange" Romney is. While it is true that Romney can come across as a 1950s sitcom father, this may not hurt him as voters see more of him.
So, even by basing his campaign on previously successful campaigns, Obama faces a number of problems in winning reelection.