We may have just gotten our October Surprise

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For weeks I’ve been asked whether I think there will be an October Surprise and what I think it’ll be. My response has been that if it’s truly a surprise, it’ll be something that none of us saw coming, and therefore none of us could have predicted it, so there was no point in randomly guessing. But now it appears we have indeed gotten ourselves an October Surprise.

Donald Trump held a rally at Madison Square Garden on Sunday, which had precisely zero chance of helping him in any way, and had a good chance of costing him votes. For all of the contrarian hot takes about how this rally was part of some kind of secret plan by Trump and his campaign to magically whatever, the obvious reality is that this was merely stupidity. Trump’s babysitters don’t know what to do with his senility, and so instead of sending him to a swing state where he could cost himself votes, they basically threw him a party in his hometown so he could feel good about himself on his way to losing. And he’s so senile, he went right along with it.

But then came the moment where a featured speaker at the rally referred to Puerto Rico as a “floating island of garbage.” It was the insult heard round the world, and it instantly took on a life of its own. Throw in the subsequent racist remarks about Latino people in general, racist remarks about Black people, and attacks on Jews, and the rally was already Trump’s worst day of 2024 before he even took the stage. By the time Trump gave his speech it didn’t matter what he said; he’d already lost the day in horrendous fashion.

For a controversy like this to matter, it has to reach beyond the people who were already planning to vote a certain way. It has to reach people who weren’t necessarily going to vote, but have now been given a reason to. It has to reach people who were tentative about whether or not to bother voting for their preferred candidate, and needed motivation. And that’s seemingly what’s now happening.

Immediately after the Puerto Rico insult, Puerto Rican superstar Bad Bunny endorsed Kamala Harris. Then Jennifer Lopez and Ricky Martin piled on. This was playing out even as the political media was rightly serving up one headline after another about how racist Trump’s rally was. Several hours later, after the damage was already snowballing, Trump’s campaign released a statement disavowing the Puerto Rico insult. But when Trump himself took the stage, he did no such thing.

The most damaging political scandals are not necessarily the ones that are the ugliest in their own right. They’re usually the ones that serve to confirm what the other side has been saying about that candidate all along. Dan Quayle was sunk for misspelling potato, a non story, but it played directly into the longstanding narrative that Quayle was a dummy. It’s the same thing here with Trump. The narrative about him for a decade is that he’s a racist. People in the middle, who don’t pay attention to politics, don’t necessarily know whether to believe that about Trump, but they keep hearing it over and over again. And now Trump has directly confirmed that narrative by having a featured speaker hurling racist insults at Trump’s highest profile rally of the election.

How bad is this going to be for Trump? Republican candidates in tight races, including Senator Rick Scott in Florida and multiple Republican House candidates, have tried distancing themselves from the scandal. They’re worried. All of today’s headlines are going to be about Trump’s racist rally. All of the questions asked of Republican House and Senate candidates for the next several days are going to be about Trump’s racist rally. This is the story now – and it’s got legs.

There are still nine days left in this election, and we’ll see if Trump’s Puerto Rico scandal has nine days of life in it. But if this keeps growing and snowballing, are we talking about Puerto Rican voters lining up around the block to vote for Kamala Harris? There are enough Puerto Ricans in Pennsylvania, Michigan, Wisconsin, and North Carolina to deliver every one of those states for Kamala. There are enough Puerto Ricans in Florida to hand the Senate to the Democrats. And there are enough Puerto Ricans on Long Island to decide the outcome of the multiple close House races there and hand the House to the Democrats.

It’s not a given that any of the above will happen. Puerto Rican voters are going to choose to do whatever they choose to do. And they’re not the only swing voting bloc in this election. We have to keep working down the stretch to get out every last vote. But we are now looking at the very realistic possibility that the “October Surprise” ends up being Puerto Rican voters lining up around the block to chase Trump and his party from power.

Note from Bill Palmer: I'll never stop fighting for you. If you appreciate my work, support me at this crucial time:
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