President Trump's full-court press for tax reform has revived scrutiny of his personal finances and highlighted the mystery that still surrounds how much he paid in taxes for most of his adult life.
Faced with a separate controversy related to the extravagant travel expenses racked up by members of his Cabinet -- primarily by Health and Human Services Secretary Tom Price -- the president's aides have struggled to downplay any suggestion that their tax reform plan caters to the wealthy men and women who hold senior positions throughout the administration.
The outline released by Trump administration officials this week contains a number of proposals that would benefit Americans of more modest income, such as an increase in the standard deduction and an expansion of eligibility for the child tax credit.
But other elements of the tax plan could overwhelmingly help the country's highest earners, such as the elimination of the estate tax and of a tax that aims to prevent wealthy Americans from using tax breaks to avoid paying too much on their income, known as the alternative minimum tax or the AMT.
And Trump, who has refused to release his tax returns despite the enormous pressure brought to bear on him during the campaign, is known to have paid as much as $31 million in income taxes in 2005 alone due to the AMT, according to a portion of his returns from that year that leaked to the media.
"To get this through, even if he wasn't wealthy, he was going to have to make the political sale of his lifetime," said Ford O'Connell, a Republican strategist. "There's a reason why this hasn't been done for 31 years. It requires bipartisan support, and frankly, Republicans get crushed in the messaging game every single time. This is solely a game about messaging."
Gary Cohn, Trump's top economic adviser and one of the key negotiators of the administration's tax plan, faced a barrage of questions on Thursday about how the proposals could further enrich the billionaire president.
"American taxpayers care about what they take home. They care about what they have to spend," Cohn told reporters at the White House. "That's what they care about. That's what I care about. I care about what I pay in taxes. I bet you, you care about what you pay in taxes."
Cohn argued the elimination of the AMT would not necessarily allow people like Trump to skirt their tax obligations because the removal of many deductions would close loopholes for those high earners.
"On the AMT, I'm not going to get into deep calculations on AMT, but at a broad-brush level, when you do the AMT, once you get rid of the deductions of state and local taxes, that's the biggest add-back in AMT," Cohn said. "AMT becomes irrelevant once you get rid of the deduction of state and local taxes."
Trump pitched his tax reform plan during a speech Wednesday in Indiana, where Democrat Sen. Joe Donnelly will face an uphill battle for his re-election next year. Donnelly is one of several vulnerable Democrats on whom Trump may lean to pass a plan that Democratic leaders have decried as a hand-out for the rich.
"I'm doing the right thing and it's not good for me, believe me," Trump said during his tax reform speech.
The potential savings his plan would bestow upon his family and other wealthy Americans quickly became one of the dominant storylines surrounding the proposal, however.
Although Trump's opponents seem to have concluded that lobbying for the release of his tax returns is futile after roughly two years of failure, they seized on the possibility that the administration's plan could pad the pockets of its highest-ranking officials amid a private jet scandal that has produced uncomfortable optics for a White House filled with independently rich officials.
O'Connell argued Democrats have exaggerated uncertainty about whether Trump's family will profit from the tax reform plan because the president plainly will, noting questions about his undisclosed tax returns are unnecessary because the answers are already clear.
"Let's say his tax returns are released, they'd still say the same thing," O'Connell said.
"Guess what, find me a president who wouldn't benefit from tax reform," O'Connell added. "Because chances are they have $100,000 to their name."
Trump and his aides, however, have labored to present their plan as a middle-class windfall that would offer as few benefits as possible to the rich while still spurring broader economic growth.
The administration has laid out an ambitious timeline for driving the reform package through Congress.
Cohn said Thursday that the White House hoped to see the plan progress through the House in October and emerge from the Senate in November and expressed his expectation that the final product would hew closely to the outline put forward by the administration this week. To do so, Republicans would need to set aside months of division and chaos to join with an unpopular president to pass legislation for which he is expected to campaign aggressively over the coming weeks.