May 22, 2014 6:04 AM EDT

The scene was familiar for a President who has raised billions: A white lawn tent, tables set with pink and purple peonies, and a few dozen millionaires who had paid good money to dine with power. Even Barack Obama’s message had a familiar ring. “We’ve got one party in Congress right now that has been captured by ideologues whose core premise is ‘No,’ ” he told the Democratic donors who had gathered on May 19, for as much as $32,400 a couple, at a private home in leafy Potomac, Md.

The President followed up with the same pitch he has used at dozens of fundraisers in every election cycle since his 2008 campaign: Vote for Democrats, toss out obstructionist Republicans and break the partisan gridlock in Washington. Of course, that prescription failed to work in 2010 and 2012, and in a sharply divided and dissatisfied nation, it is even less likely to succeed this November. Redistricting and midterm-voting patterns have given Republicans a virtual lock on the House of Representatives and a coin flip’s chance at taking the Senate. The best Obama can hope for is more of the status quo he can’t stand.

But the President hasn’t found a new pitch to match this new reality. With at least seven May fundraisers scheduled in four states, he is stuck traveling the country peddling short-term hope while his team puts more faith in voting and demographic trends they believe favor Democrats in 2016. At times, the frustration sneaks through. “The debate we are having right now is about what?” he pleaded in Potomac. “Benghazi? Obamacare? And it becomes an endless loop. It’s not serious. It’s not speaking to the real concerns that people have.”

And so the paradox of his presidency has been on full display in places where only paying guests can attend. The most gifted fundraiser and campaigner of his generation can’t quite pick the lock of governing. The purple nation he promised has not come to pass. The partners he thinks he deserves answer to voters he cannot woo. And the debates he yearns for remain out of reach.

With his approval rating settled in the low 40s, Obama looks increasingly resigned to riding out his final years managing world crises and a tattered federal government, while doing what he can by executive action. “I’m at the tail end of my fifth year in office,” he said on that Potomac lawn, “and that gives you some perspective.” A solution, however, remains elusive.

This appears in the June 02, 2014 issue of TIME.

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