Donald Trump is a shameless flip flopper. Can Ron DeSantis make voters care?

It’s been a running joke since even before his 2016 run, but Trump has taken both sides on just about anything you can take a side on. He’s been a third party presidential hopeful, a New York social liberal, and a nonstop Monday morning quarterback on cable and radio and especially Twitter, with a decades-long trail of contradictory positions along the way.

But so far nobody has managed to damage him much with it, and it hasn’t been for lack of trying.

“Cruz tried it, Jeb tried it, Marco tried it,” said Tim Miller, a former top aide to Jeb Bush’s 2016 campaign and specialist in opposition research. “That doesn’t mean it won’t work in another context, but is it really going to be his old white papers from the Reform Party that do it?”

As Trump’s critics tried in vain to point out during his first run, even some of his most famous policy stances in 2016 — opposing Mideast interventions, tacking hard right on immigration, and even keeping out Syrian refugees — were flip flops, and often recent ones.

In one contentious Fox News debate that year, the moderators were so frustrated with Trump’s slipperiness that they came prepared with video clips of him contradicting his stances in his own words, to little avail. He even abandoned an immigration position from his own campaign website in the middle of the debate, saying “I’m changing, I’m changing” (the campaign then quickly walked that flip flop back).

“I think he can say two opposite things in the course of a minute and believe both of them,” his then-rival Sen. Ted Cruz, R-Texas, groused afterwards.

Several top Never Back Down officials — including Ken Cuccinelli and Jeff Roe — were key players on that 2016 Cruz campaign, which sought to consolidate conservative support by highlighting the senator’s consistency on issues that activists care about most (albeit with some mid-campaign flips of his own).

There are signs DeSantis might pursue a similar plan and hope for better results with an earlier and more focused attack that uses Trump’s flip flops to undermine his credentials on the right.

“We’re always going to look for an opportunity to highlight the contrast between DeSantis delivering on his promises and Trump doing something different than what he said he would do — or being pulled in a different direction depending on who he talks to last,” one advisor to Never Back Down told Semafor.

In addition to responding to Trump’s attacks, one ad from the super PAC highlighted Trump’s momentary interest in gun control measures favored by many Democrats after the Parkland high school shooting. DeSantis has also suggested that Trump was bullied by his advisors during the pandemic into not overriding CDC guidance and firing Dr. Anthony Fauci, and taken credit for prodding him to carry out his promise to move the embassy in Israel.

It will take work, though. Whatever he’s said before, Trump’s brand with Republican voters in 2023 is still the candidate who pledged not to touch Social Security and Medicare in his first election (don’t ask about his Medicaid promise) and then passed a fairly conventional Republican tax cut. DeSantis’ brand is still being defined, and he has not fully renounced his old positions yet or released a campaign platform that might override them.

“DeSantis, as an elected official, congressman, and politician, thought it was a good idea to rip Social Security and Medicare from seniors,” Steven Cheung, a spokesman for the Trump campaign, said when asked about the former president’s past statements. “President Trump will actually protect those important programs from being eliminated.”

Trump can point to a 6-3 Supreme Court majority that overturned Roe v. Wade as proof of his conservative commitments — something he couldn’t do in 2016. And, of course, he’s far from the only politician to lie or change positions, even if he’s a massive outlier on frequency and severity. There’s always someone else’s inconsistency to point to if supporters need further rationalization (Joe Biden’s 50-year career is especially ripe) and he has no shame about doing so.

Finally, there are plenty of skeptics who wonder whether any kind of policy checklist approach towards “true” conservatism can be effective against Trump, whose appeal seems to come from somewhere more visceral.

“I’ve never heard somebody say they really liked Donald Trump because of his stance on a particular position,” Alex Conant, another 2016 veteran who worked on Rubio’s campaign, said. “They like him because he’s a fighter.”

Democrats have been engaged in their own struggle with Trump on this topic lately. After they pointed to Trump’s 2019 comments arguing the debt ceiling was “a very, very sacred thing in our country” that should not be used as a hostage in negotiations, Trump blithely responded in his CNN town hall that the situation was different “because now I’m not president” and that Republicans should force a default if necessary. He was consistent on that point, at least: fact checkers noted when he was president that he called on Republicans to use the debt ceiling as leverage under President Obama as well.

While Trump sometimes seems invulnerable to attack, polls have long indicated voters are aware of his honesty issues, and they may have played a role in his 2020 loss. A Quinnipiac Poll in March found only 29% considered Trump honest, the lowest figure they’d ever recorded for him, while 65% said he was not. For DeSantis, voters were split 39-39, suggesting he may have a better opening to make his case.