Representative Maxwell Frost of Florida’s 10th District entered Jubilee’s Surrounded ready to defend the Democratic agenda. Instead, one of Congress’s youngest progressives was dropped into a room with 20 Baby Boomers, and quickly learned that it is harder to sell old Democratic promises to the generation that has already seen them fail. 

The format places one guest in the middle of 20 ideological opponents, who rotate through rapid-fire debates on a range of issues. In this case from affordability, to the promise of socialism, to whether or not the American dream still exists. For Frost, it became a generational collision as the young congressman made the case for modern progressive politics to voters with decades of experience watching Washington promise change after change, and doing little more than spend more money, raising taxes, and leave ordinary Americans behind.

One of the episode’s most viral exchanges came when Rep. Frost turned to affordability, now one of the country’s most pressing political concerns. Americans are right to be frustrated by rising prices, housing costs, and the growing difficulty of building a stable life. But the debate over “affordability” has also become tangled up with an expectation that the government should simply provide more at taxpayers’ expense.

As Frost explained the crisis, alongside how Democrats plan to solve it with greater spending and higher taxes, one guest offered a far more direct answer.

"I want to teach people is that we're going to make smart decisions as a nation, not just based on the fact that I went through this or you have to go through it, but how can we uplift our economy?" Rep. Frost said. "You saying that young people are all of a sudden going to think everything that can be paid for by other people is just not true. Why? We're not dealing with one crisis here. It's not just a crisis of student debt. We're dealing with the housing affordability crisis. Healthcare is too expensive. Getting a car is too expensive. You were talking about the student loans on top of that, the groceries, every little thing that we consume in life has gone up."

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"The reasons that things go up, three things, taxation, regulation, and currently illegal immigration," the guest said. "Those are the reasons.

In another exchange, a different guest took aim at Democrats’ push for higher taxes. As the pair debated the incentives created by taxation, Frost argued that taxes should not be treated as a punishment, but as a means of ensuring that everyone benefits from public services. 

The guest countered that, whatever Democrats call it, the party’s growing embrace of higher taxes and greater government control reflects an increasingly comfortable drift toward socialism.

And in one of the episode’s most consequential exchanges, Frost and a third guest debated whether the American Dream still exists. Democrats have increasingly spoken as though it does not, as if rising costs and economic uncertainty have made advancement impossible for ordinary Americans. 

There are real obstacles, high taxes, burdensome regulation, inflation, and a political culture increasingly comfortable with redistribution rather than growth. But the American Dream remains overwhelmingly attainable. In fact, Frost himself is evidence of it as the first Gen Z member of Congress, who worked as an Uber driver to help make ends meet while running for office.

Baby Boomers may be the butt of plenty of jokes, but they possess something younger generations too often dismiss: the perspective that comes with decades of experience. They have watched politicians make promise after promise, only to see little change for working Americans beyond higher costs, higher taxes, and more government control. That perspective may not always be welcomed, particularly by a younger Left increasingly drawn to socialism. But it remains essential if America is going to resist the idea that the country’s problems can be solved by repeating the same failed ideas.