CNN  — 

For months on the campaign trail, President Donald Trump has questioned Joe Biden’s mental acuity and used his branding skills to cast his opponent as someone who isn’t up for the job.

The wisdom of that strategy will be tested as the two men enter the debate arena Tuesday night.

Trump will meet the former vice president for their first one-on-one matchup in Cleveland, Ohio, in a precarious position five weeks before the election. He faces an imperative to rattle his opponent or force him into a mistake that shakes up the race at a time when he is trailing Biden by nine points in an average of national polls – with ballots already being cast – and newly on the defensive after a New York Times exposé showing he only paid $750 in federal income taxes the last time he ran for president and his first year in office.

In the lead up to the debate, Trump – who has never proved to be a particularly agile debater – has shown few signs of a coherent strategy to dramatically alter the course of the race. But these three consequential debates present his last chance to do so. To the chagrin of some of his advisers, Trump has managed to set perilously low expectations for Biden as travels around the country telling voters the former vice president has no idea “what’s going on.”

“He’s a dumb guy, a dumb guy, always known as a dumb guy,” Trump said during a Middletown, Pennsylvania, rally Saturday.

The President also does not seem to have changed many minds as he continues to tout his “perfect” handling of the coronavirus pandemic, which has killed more than 200,000 Americans – even though a majority of voters give him poor marks on that score. And Trump is all but certain to squander precious minutes during the debate re-litigating debunked conspiracy theories about Ukraine, Russia, Hillary Clinton, Hunter Biden and his own impeachment that resonate with few voters beyond those who already support him.

He previewed one of those theories at his White House press conference Sunday evening when he baselessly charged that Biden is on drugs, repeating claims from a tweet earlier that day.

“I’m not joking. I’m willing to take a drug test and I think he should too,” Trump said from the White House podium, as two of his debate coaches, former New Jersey Gov. Chris Christie and former New York Mayor Rudy Giuliani, looked on. “Check out the Internet. Plenty of people say it,” Trump said.

View Trump and Biden head-to-head polling

Biden has generally ignored those kinds of wild accusations, and when asked Sunday in Wilmington what he needs to accomplish in the debate, he replied: “Just tell the truth.”

Biden’s deputy campaign manager Kate Bedingfield responded to Trump’s drug test taunts late on Sunday: “Vice President Biden intends to deliver his debate answers in words. If the president thinks his best case is made in urine he can have at it. We’d expect nothing less from Donald Trump, who pissed away the chance to protect the lives of 200K Americans when he didn’t make a plan to stop COVID-19,” she said in a statement.

Passing the commander-in-chief test

With the debate looming large as one of their last chances to persuade voters, it’s an open question whether both men can keep the debate substantive Tuesday night and avoid the swift descent into the gutter politics that Trump seems to relish.

Republican and Democratic strategists pointed out in interviews this week that the debates are unique this year because Trump is such a polarizing figure and many voters will tune in with their opinions already hardened and unlikely to change.

Still, both men need to reach those pockets of voters they have battled over throughout the election: suburban moderates, soft Republicans and center-right independents, particularly those within blue-collar families in the Midwest, who gave Trump a chance in 2016 and are now skeptical that he deserves another four years.

With Biden expected to drill Trump for his cavalier and often heartless response to the pandemic, several GOP strategists said Trump’s best chance of winning back those voters is to avoid being drawn into a defensive posture on his handling of the coronavirus – and instead focus on the economy.

That is one key area where Trump has maintained voter trust, while portraying Biden as an empty vessel for socialist-leaning forces in the Democratic Party who want to raise taxes and increase regulations that the President says would cripple small businesses.

“If you are Trump, part of your mission here is making sure that any center-right voter who voted for you in 2016, and mostly votes Republican, has a reason to stay with you. The best policy ground for him to fight upon is the economy,” said Scott Jennings, former special assistant to President George W. Bush and a CNN contributor.

Jennings added that as Biden tries to dwell on Trump’s missteps in his handling of the pandemic, the President “can’t get bogged down re-litigating the past” and must “constantly try to move the conversation to more fertile ground – and that’s the future, the recovery.”

Jennings acknowledged that while some of those center-right voters don’t approve of Trump when it comes to the coronavirus, “it is entirely possible, maybe even likely, that group would be willing to concede they trust Trump more on the economic recovery from coronavirus than they would trust Biden.”

Biden has an opportunity to persuade anxious voters that he would be the steady, competent and experienced commander-in-chief who could lead the nation out of its three-pronged crisis of the pandemic, the recession and the roiling debate over systematic racism and police brutality.

The New York Times reporting about Trump paying no federal income taxes in 10 out of 15 years, beginning in 2000, could help Biden drive home the contrast between Scranton, Pennsylvania, and Park Avenue that has become a key part of his messaging.

The former vice president’s challenge Tuesday night will be to “defend his record without being defensive” as Trump tries to “rattle his cage” with offensive taunts and personal attacks about his family, said Dan Pfeiffer, who was former President Barack Obama’s senior adviser for strategy and communications at the White House. (Trump telegraphed that part of his strategy with his references to Hunter Biden at his Sunday news conference).

“What has put Biden in this position (as the leader in the race) is that he seems like someone who could be president,” Pfeiffer said. “There’s a stature gap between Biden and Trump, and Biden has to be careful not to narrow that gap by getting pulled down in the mud with Trump.”

Another key test for Trump is whether he can resist his worst instincts in the form of gross exaggerations, factual inaccuracies and fringe conspiracy theories that have eroded voters’ confidence in his leadership.

While Trump’s speeches and interviews are often rife with inaccuracies, Frank Fahrenkopf, the co-chair of The Commission on Presidential Debates, told CNN’s Brian Stelter Sunday that it won’t be the debate moderator’s role to fact check the candidates in real time Tuesday night.

Fox News’ Chris Wallace will moderate the first debate, which is expected to focus on six topics: “The Trump and Biden Records,” “The Supreme Court,” “Covid-19,” “The Economy,” “Race and Violence in our Cities” and “The Integrity of the Election.”

“The moderator is a facilitator,” Fahrenkopf said on CNN’s “Reliable Sources.” “We don’t expect Chris or our other moderators to be fact-checkers. The minute the TV is off, there are going to be plenty of fact-checkers in every newspaper and every television station in the world. That’s not the role, the main role of our moderators.”

Trump has to remain on the offensive, said Brett O’Donnell, a veteran debate coach who prepared GOP presidential candidates including George W. Bush, John McCain and Mitt Romney for some of their presidential debates. “I’ve described this as the ultimate disrupter versus the consummate career politician,” O’Donnell said.

Facing Biden – whom O’Donnell describes as “the most conventional politician in a long time to be a party’s nominee” – Trump has a chance to use “Biden’s record from 47 years in politics to flesh out where he would take the country” and should also try “to push him as far left as possible,” O’Donnell said, to blunt Biden’s appeals to moderate voters.

“What makes the President difficult to debate is that he does stuff through branding. He doesn’t make these long-drawn out substantive arguments. … He just sort of brands you to make a point and then hopes it will be filled in after the fact,” O’Donnell said.

Biden’s ability to rebut those labels – whether about his mental acuity or the notion that he would lead the country toward socialism — will be one of his central challenges.

Polling gaps for both Trump and Biden

The President will also be looking for ways to address his enormous gender gap with Biden, who is leading him among female voters by some 30 points. (Biden is trailing Trump with men).

Trump may have taken a step in that direction with his Supreme Court nomination of Amy Coney Barrett, a mother of seven, to the Supreme Court in a well-choreographed ceremony Saturday night in which the federal appellate judge skillfully conveyed the attributes of her judicial philosophy while looking like a relatable figure to the key voting bloc of suburban independent and Republican-leaning women.

Trump has alienated many female voters with his style, his tweets and his callous comments about coronavirus deaths – like his recent statement at an Ohio rally that the coronavirus “affects virtually nobody” just as the US was crossing 200,000 deaths.

The ability of both Trump and Biden to try to make the debate a direct conversation with the average voter in the midst of their heated exchanges will shape the extent to which they are able to persuade. One aspect of that is showing Americans they understand the pain and anxiety the pandemic has wrought — though empathy has never been an area of strength for Trump.

“Both of these guys forget their audiences, and it will be interesting to see if they’re just debating each other all night long,” O’Donnell said. “The President has a great opportunity to speak to some of those suburban security moms through what’s happening in the cities; and he has an opportunity to speak to them through the Supreme Court pick.”

Whether he seizes that opportunity is another question. Because while message discipline and restraint may be the best tools he has to turn around his flagging campaign, Trump has often failed to use them.