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Donald Trump and Hillary Clinton
Photo illustration by Sarina Finkelstein for Money; Getty Images (2)

With about a month and a half to go before America chooses its next president, Democrat Hillary Clinton and Republican Donald Trump are slated to square off in their first debate Monday night at Hofstra University in New York. Among the three topics moderator Lester Holt is slated to tackle is one that's close to our hearts at Money: "Achieving prosperity."

It's already clear that the election—coming eight years after the worst financial crisis in a generation—will be remembered as a battle over the direction of the U.S. economy. Trump, a well-known businessman without political experience, captured the Republican nomination largely by promising to protect middle-class jobs, even bucking his party's traditional stance on issues like trade and immigration. Clinton, the former First Lady and Secretary of State, represents continuity, a chance for Americans to stick with the steady, if slow, gains they've seen under President Obama.

But for all the political rhetoric—and some fairly detailed policy proposals on issues like taxes and healthcare—there is still plenty we don't know about where the candidates would lead the country. Here's what Money would press them to tell us.

On boosting middle-class incomes

The wind-up: While the stock market has long recovered from the Great Recession, and the unemployment rate is a healthy 4.9%, middle-class incomes are still below where they were in 1999. Meanwhile the United States has lost millions of manufacturing jobs over the last generation. Neither of you has put forward a comprehensive, realistic plan to help them.

The question for Clinton: "Secretary Clinton, you've said that America needs to 'meet the challenges families face in the 21st century.' According to budget scorers, your plan's biggest spending proposals include cutting the cost of college and childcare and improving our infrastructure. Those are admirable goals, but if I'm a 50-year-old factory worker, childcare and college are no longer my priorities. And while a new building project in my city might spell a job offer, President Obama has failed to get a similar program through Congress. At least among whites, you're badly losing voters in my demographic to your rival. What else would you do to help me boost my income?"

The question for Trump: "Mr. Trump, to your credit, you've put the ailing middle class at the rhetorical center of your campaign. But most mainstream economists say that your suggested remedies—deficit-swelling tax cuts, new tariffs on foreign goods from Mexico and China, and deporting millions of workers—would hurt, not help. Moody's Analytics projected that even a scaled back version of your plan would send the U.S. into a recession lasting until 2019. If the professionals turned out to be correct and your policies had the effect of shrinking the economy, would you reverse course, or double down?"

On healthcare

The wind-up: Twenty million Americans have gained health insurance under the Affordable Care Act, a.k.a. Obamacare. This represents a significant expansion, but enrollment has lagged projections made when the law was enacted in 2010. The fourth Obamacare open enrollment period starts a week before the election, with higher premiums and fewer choices than last year.

The question for Trump: "Mr. Trump, you plan to seek repeal of Obamacare on your first day in office, and you've pledged to end the individual mandate that requires most consumers to buy coverage or pay a penalty. On the other hand, you have voiced support for a very popular provision of the Affordable Care Act that prohibits insurers from denying coverage or charge more to people with pre-existing conditions. Most health policy experts agree that you can’t guarantee coverage to everyone without an individual mandate. What would you say to reassure the 20 million who have gained coverage under Obamacare that they will not lose their coverage in a Trump administration, especially those with pre-existing conditions?"

The question for Clinton: "Secretary Clinton, you have proposed expanding Obamacare to include a “public option,” a government-run choice to sit alongside the plans from private insurers. Obamacare has struggled in part because not enough healthy young people have signed up to offset the costs of covering older, sicker enrollees. UnitedHealth Group and Aetna are among the insurers who will scale back participation in 2017, citing losses. How would you encourage—or enforce—the participation of more young and healthy millennials? And how would you foster competition among insurers on the exchanges—one of the main goals of the law—if a public option draws business away from them?"

On Social Security

The wind-up: Both candidates have promised to protect Social Security it. In your case, Secretary Clinton, to expand it slightly by boosting benefits for surviving spouses and retired caregivers. The problem? With millions of boomers retiring, Social Security is projected to prompt a $69 billion shortfall for 2017, ballooning to nearly $200 billion a year by 2024. Neither of you has proposed realistic ways to address these shortfalls.

The question for Clinton: "Secretary Clinton, while you have proposed raising taxes on those making more than $250,000—which would net roughly $1.2 trillion in additional federal revenue—you have said you want to use all of this money to fund education, childcare, and infrastructure programs. In other words, while your plan wouldn't make Social Security's budget problems worse, it wouldn't fix them either. When push comes to shove, how would you propose to fill the hole: By cutting your ambitious social programs or raising taxes on the upper-middle class?

The question for Trump: "Mr. Trump you haven't explained how you'd fix Social Security, either. In fact, the policy wonks that call Secretary Clinton's plan a stretch label yours downright "unrealistic." You would cut taxes by anywhere from $4.4 trillion to $5.9 trillion. You have suggested this could be paid for with 3.5% GDP growth spurred by unleashing America's entrepreneurial mettle. But you haven't convinced many experts—even conservative ones—that this is plausible. So without an economic miracle, what would you do: Abandon your historic tax cuts or cut Social Security benefits significantly?

On the Federal Reserve

The wind-up: With the President and Congress unable to compromise on government spending over the last six years, the Federal Reserve has borne the responsibility of holding up the U.S. economy. This has resulted in near-record-low interest rates that threaten investor confidence. Meanwhile, the Fed has more than $4 trillion on its balance sheet.

The question for Trump: Throughout your campaign you’ve personally attacked Fed Chair Janet Yellen. You’ve said that she “should be ashamed of herself” and that the Fed has maintained low interest rates for “political” reasons. But since inflation isn’t at the level the Fed wants it to be, and wages aren’t rising as fast as before the recession, isn’t there a legitimate reason for the Fed to keep rates low? And if you are elected in November, will you publicly call on Yellen to aggressively raise rates?

The question for Clinton: "Many economists are worried that an indefinite period of low interest rates will make the financial markets less stable. The Federal Reserve Bank of Boston president, for example, recently gave a speech where he worried about asset prices growing too fast because of low rates. If elected, will you renominate Yellen as Fed Chair in 2018? And if not, will you demand that your nominee worry as much about potential market bubbles as about stimulating the economy?"

On college costs

The wind-up: Surveys show that American families are increasingly worried about how they’re going to pay for their children’s college education, and that many students are leaving college today burdened by tens of thousands of dollars of educational debt. We’d like to ask both candidates what you believe to be the federal government’s role in addressing this problem.

The question for Clinton: “Secretary Clinton, you've proposed making tuition at public colleges and universities free for in-state students whose families earn $125,000 or less a year. Some of the money would come from the federal government and the rest from the states themselves. Given that you'd likely have to get this plan through a Republican Congress, and that many state legislatures have recently been making substantial cuts to public university budgets, why do you—and why should the American people—believe this can really happen?”

The question for Trump: “Mr. Trump, your national co-chair and policy adviser Sam Clovis indicated in a May interview that you were opposed to Democratic proposals to make college free. More recently you threatened to crack down on universities taking "massive tax breaks for their massive endowments" if they didn't devote more of those funds to reducing the cost of tuition. It's true that some colleges have multibillion-dollar endowments, but more than half have no such reserves to draw on. How would the millions of students who attend those colleges benefit from your plan?"