Former Massachusetts governor Mitt Romney announced late Friday that he had sought an extension to file his 2011 tax returns, the newest piece of evidence of the political problem those documents have and will continue to cause him in his presidential bid.

Republican presidential candidate, former Massachusetts Gov. Mitt Romney waves after speaking at the National Rifle Association convention in St. Louis, Friday, April 13, 2012. (AP Photo/Michael Conroy)

The truth of the matter is that Romney is in a damned if he does/damned if he doesn’t situation when it comes to his tax returns.

For their part, the Romney campaign insists that the postponement of his filing has nothing to do with political timing and everything to do with the fact that some of the companies in which he invested have yet to report their earnings — making it impossible for him to calculate his income.

Looking back at how the tax return issue played out in the Republican presidential primary, it’s clear the political danger that the tax return issue poses for Romney. Romney clearly had zero interest in releasing his tax returns during the heat of the nomination fight but after a loss in South Carolina and considerable pressure from his opponents to disclose his income, Romney bowed to the political inevitable.

While releasing the returns lanced the immediate political boil for Romney, the fact that he had made $42 million without earning any income in 2009 or 2010, had a Swiss bank account and paid a tax rate of just 13.9 percent reinforced the “Romney as other” narrative that his opponents — Republican and Democrat — were pushing.

It also marked perhaps Romney’s low ebb in the race — he righted the ship with a win in Florida on Jan. 31 — and likely reinforced to his campaign that there is no political benefit to releasing his returns any time soon.

Of course, Democrats see the Romney tax return issue as a major opportunity to cast him as insufficiently transparent, begging the question of what exactly Romney is hiding.

Seeking to ramp up the pressure, President Obama and Vice President Joe Biden both released their 2011 tax returns on Friday. New York Sen. Chuck Schumer held a conference call today pushing the idea of Romney as anti-transparency. A new ad from Priorities USA Action, the main super PAC supporting President Obama, makes mention of the fact that Romney made $21 million in 2010. And so on and so forth.

Campaign politics being what it is, Democrats will keep up that tax return drumbeat against Romney for the foreseeable future. It’s an issue that fits perfectly into the narrative that President Obama’s reelection campaign wants to tell about the former Massachusetts governor: That he is a member of the wealthiest sliver of American society, and, therefore, hopelessly out of touch with what average people need or want.

The Romney campaign is not dumb. They know that Romney will take incoming from Democrats every single day between now and when he released the returns. (They are trying to push back too — noting that Democratic National Committee Chair Debbie Wasserman Schultz is refusing to release her own tax returns.)

But, they also know that the week after he became — for all intents and purposes — the Republican presidential nominee is not the time to release his tax returns and give up the momentum they are trying to build. (Perhaps an early sign of that momentum: the first Gallup general election tracking poll released today has Romney at 47 percent to Obama’s 45 percent.)

The campaign’s vagueness about when they might release the returns is intentional. It gives them considerable wiggle room to pick the right time — aka when no one is around or paying attention to politics — to put the returns out. (Early August, anyone?)

Put simply: The Romney team knows that the candidate’s tax returns are a political loser for them. The best way to deal with losing issues is minimize them to the greatest extent possible. Filing for an extension — whether that was by necessity or born of political calculation — to release his returns allows Romney to handpick that moment.