Mitt Romney’s campaign has faced criticism from both sides of the aisle for declining to publicly disclose more than two years’ worth of tax returns. The Fix’s Chris Cillizza and Aaron Blake reported:

Romney’s biggest struggle in the general election — and the Republican presidential primaries in 2008 and 2012 — is and has been convincing people that he understands them.

His Mormon faith (a religion shared by a tiny fraction of the American public) coupled with his upbringing (his father served as governor of Michigan and ran for president) are two major differences between the former governor and many of the people he is trying to win over.

Add his personal wealth — Romney made nearly $22 million without earning a salary in 2010 — and the former Massachusetts governor faces of trifecta of problems as he seeks to convince voters that he understands them at a gut level.

That struggle to connect is borne out in polling. In a Washington Post-ABC News survey conducted this month, 50 percent of people said that Obama “better understands the economic problems people in this country are having,” while 40 percent said that Romney had a better grasp of those issues. (Among political independents, the news is better for Romney; 44 percent say Obama better understands the economic problems faced by regular people, while 42 percent say Romney does.)

It’s not likely that Romney — whether or not he releases a substantial portion of his past tax returns — will ever be entirely relatable to the average person. And in an election in a time of relative prosperity, that connection issue might doom his chances.

Washington Post Opinion columnist Matthew Yglesias provided some hypothetical scenarios of what could be found in Romney’s tax returns, including profits and a low tax bill as a result of the 2007 economic crash:

The vast majority of American families lost wealth in the housing bust of 2007-09 and the financial crisis that came in the middle of it, and millions lost jobs or earnings. But it was possible for a canny or lucky investor to profit from the chaos — especially for a wealthy individual with access to unusual financial products. Maybe Romney made a lot of money through bets on skyrocketing foreclosures or well-timed investments in bailed-out banks. There’s nothing wrong with smart financial planning, but making money on the crash could be awkward for a politician.

President Obama’s ad campaign has also played up the fact that Romney at one point had a Swiss bank account. Yglesias also provided analysis of what could lie in these records, as they were not provided as part of his 2010 tax return disclosure:

We know from the tax documents Romney has released that he once had a Swiss bank account, a fact that the Obama campaign has played up in ads. But his 2010 tax return did not include a Report on Foreign Bank and Financial Accounts form (“FBAR” to accountants) detailing his offshore investments. In 2009, the Swiss government began to relent on its traditional banking secrecy rules, and banks turned over information about tens of thousands of American tax scofflaws to the U.S. government. To help deal with the crush, the IRS staged a limited-time amnesty in 2009 for American citizens with previously nondisclosed foreign accounts to pay their back taxes without penalty. It’s possible that earlier tax documents or the 2010 FBAR would show that Romney took advantage of the amnesty. While legal, this would amount to a problematic confession of past wrongdoing.