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Ramaswamy vs DeSantis: Who Will Be the One to Challenge Trump?

(David Molnar/The Republican via AP)

We are less than five days away from the first 2024 Republican presidential primary debate and it is already shaping up to be an interesting affair. If you would have asked most on the right who would be chasing at former President Donald Trump's heels, the answer would have been clear: The second favorite was bound to be Florida Gov. Ron DeSantis. But we have already seen how that has turned out, haven't we?

After a lackluster announcement of his presidential campaign on X, the social media platform formerly known as Twitter, and a few missteps here and there, DeSantis has failed to make the expected splash. This has allowed entrepreneur and author Vivek Ramaswamy to threaten the governor's position as second-place frontrunner. The question is: Which man will pull far enough ahead to challenge Trump, who still retains a healthy lead over the rest of the pack?

Up until this point, polling has shown DeSantis ahead of all other contenders aside from Trump. But two recent polls show that Ramaswamy has rapidly closed the gap. In one survey, the entrepreneur pulled one point ahead of the governor. A recent Emerson College poll showed the two candidates tied at 10 percent. This latest figure shows an 11-point drop for DeSantis from the previous survey.

It appears Team DeSantis recognizes the threat Ramaswamy poses to their position among Republican candidates. The New York Times reported on documents coming from a firm working with a pro-DeSantis organization detailing the governor's strategy in the upcoming debate:

Ron DeSantis needs “to take a sledgehammer” to Vivek Ramaswamy, the political newcomer who is rising in the polls. He should “defend Donald Trump” when Chris Christie inevitably attacks the former president. And he needs to “attack Joe Biden and the media” no less than three to five times.

A firm associated with the super PAC that has effectively taken over Mr. DeSantis’s presidential campaign posted online hundreds of pages of blunt advice, research memos and internal polling in early nominating states to guide the Florida governor ahead of the high-stakes Republican presidential debate next Wednesday in Milwaukee.

The trove of documents provides an extraordinary glimpse into the thinking of the DeSantis operation about a debate the candidate’s advisers see as crucial.

“There are four basic must-dos,” one of the memos urges Mr. DeSantis, whom the document refers to as “GRD.”

“1. Attack Joe Biden and the media 3-5 times. 2. State GRD’s positive vision 2-3 times. 3. Hammer Vivek Ramaswamy in a response. 4. Defend Donald Trump in absentia in response to a Chris Christie attack.”

Meanwhile, Team Ramaswamy appears nonplussed about the idea of going toe-to-toe with DeSantis. In response to the revelation about the governor's debate strategy, Tricia McLaughlin, a senior adviser for the entrepreneur, said his job "is to introduce himself and his vision to the American people," and that the "boring, canned attack lines from a robotic candidate doesn't change that."

She added: "If DeSantis struggles to use a spoon, I can't imagine he is particularly agile with a sledgehammer." This was a reference to Trump's assertion that the governor eats pudding with his fingers. You gotta love politics in 2023, right?

Both Ramaswamy and DeSantis will be under gargantuan levels of pressure to perform in this first debate. Indeed, it could have a heavy impact on the trajectory of the rest of the race. These candidates will have to employ strategies that play their strengths while playing on the weaknesses of the other.

Let's start with DeSantis. The governor still remains a star on the right due to his governance of the Sunshine State. His handling of the COVID-19 pandemic, while not as liberty-focused as some have suggested, is still leaps and bounds better than many of his contemporaries. With a booming economy in Florida and a pugilistic approach to the evils of the woke movement, he remains a formidable foe despite his lagging campaign.

As DeSantis' campaign undergoes a reset, a powerful showing at the debate could be the boost the governor needs to re-establish his position as the best candidate to replace Trump. The fact that his strategy was leaked to the press could be a setback, but not a major one if he plays his cards right. DeSantis needs to emphasize his performance as governor and the bona fides he established as a worthy opponent of the activist media. 

Unlike Ramaswamy, the governor actually has governing experience, a fact he should hammer home repeatedly. He must continually remind the base why they fell in love with him in the first place. While Ramaswamy has relied on his charisma and positioned himself as a man with ideas, DeSantis can counter by pointing out what he has accomplished already in the state of Florida.

A positive step that the governor's campaign has taken over the past few weeks has involved focusing on immigration and laying out a plan for the economy instead of basing his message primarily on being an anti-woke crusader. If he continues in this direction, and articulates a bold vision at the debates, he might just be able to fend off his opponent's attacks.

On the other hand, Ramaswamy, as a newcomer and outsider, presents a fresh new face for the conservative voting base. Having been a highly successful entrepreneur and written the book on woke corporatism, he has a decent shot at being the figurehead to challenge the former president.

Ramaswamy's superpower lies in his ability to communicate his ideas and convictions in a way that resonates with those who listen to him. As someone who isn't a fan of many of his stances, I can still acknowledge that the man is a persuasive communicator. Not only that, there is no denying that the candidate is a highly intelligent figure in the conservative movement.

Team Ramaswamy might benefit from focusing on positive messaging rather than going on the attack against DeSantis. Yes, this is a primary debate, so he will have to show he can throw some punches. But his strength lies in his ability cast his vision for America and bring new ideas to the table. The candidate has suggested reforms like raising the voting age and getting more militarily antagonistic with Mexican drug cartels. These positions seem to have challenged the imaginations of many on the right---even those who may not fully agree with them.

Also, it is worth noting that Ramaswamy is the youngest person ever to run for president. The GOP has historically struggled to win over younger voters. The candidate would be wise to emphasize the fact that he might be able to succeed where other conservative politicians have not with this demographic. If Ramaswamy continues to brand himself as a bold newcomer with fresh ideas, he might have what it takes to persuade the base to give him a chance over DeSantis.

For both candidates, this debate will be critical. Depending on how they perform, the event could make or break their campaigns depending on how well they keep their composure while brushing off the inevitable attacks that will come from the rest of the field. The fact that Trump will not physically be in the room gives these individuals a better chance of establishing themselves as serious contenders. If either of these folks wishes to gain the lead, they better come prepared with their A-games.

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