When Jeb Bush first made clear that he was running for president, one of the knocks against him was that he might be a bit rusty out on the trail. The last time he’d run for office was in 2002, when he was reelected governor of Florida. Thirteen years is a long time to be away from the day-to-day life of campaigning. People’s attitudes change, the prevailing political sentiment changes, and suddenly you have to police every single word you say to deny fodder for the traveling press corps and the army of gaffe-hungry video trackers stalking your every movement.

And Jeb proved himself a stumbling, gaffe-ish candidate early on. What’s amazing, though, is that he hasn’t really gotten any better as time has passed. He’s still gaffing and tripping over his words and saying things that don’t make tons of sense. Last week, Jeb went down to South Carolina and served up his best Mitt Romney impersonation, explaining how he’ll win over traditionally Democratic black voters:

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Bush pointed to his record on school choice and said that if Republicans could double their share of the black vote, they would win the swing states of Ohio and Virginia. "Our message is one of hope and aspiration," he said at the East Cooper Republican Women’s Club annual Shrimp Dinner. "It isn't one of division and get in line and we'll take care of you with free stuff. Our message is one that is uplifting -- that says you can achieve earned success."

That “free stuff” bit is what’s causing Jeb trouble, with its implied message that black voters vote Democratic because they want or expect government handouts. There’s also the noticeable incongruence of a presidential candidate with two former presidents in his immediate family evangelizing the need for black voters and others to make their own success in life. But perhaps the biggest problem for Jeb is the disconnect between his message and the policies he’s proposing.

Jeb’s dismissal of “free stuff” in favor of hard work and aspiration comes off as hollow when you remember that he just released a tax plan that is specifically designed to make wealthy people much, much wealthier without them having to lift a finger. The plan is dressed up as a “populist” attack on a narrow slice of wealthy America, but overall more than 50 percent of the tax cuts he’s proposing would be funneled right to the top one percent of earners. Those lucky few would receive, on average, an $82,000 tax cut, while the lowest earners in the country would pull in a cool $227. If I’m a lower income voter of any race and I hear Jeb Bush extolling “earned success” and lambasting the notion of government handouts for people like me while he’s rewriting the tax code to send several hundred billion dollars to himself and his country club pals, I’d be inclined to think he’s full of shit.

This is standard-issue Republican tax policy, but other Republicans are a bit smoother when it comes to squaring the nakedly regressive quality of their tax proposals with their professed concern for the little guy. Marco Rubio, for example, has offered tax plan that would represent a massive giveaway to the country’s wealthiest people – taxes on their incomes would be cut, and taxes on their investments and estates would be eliminated. It would redistribute income upwards much in the same way that Jeb’s plan does. But Rubio argues that this massive subsidy for rich people will help the middle class because the wealthy will invest it and create jobs like the one his immigrant father held down as a young man.

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But Jeb doesn’t have an up-from-nothing story that he can use to convince people to vote against their own economic interests. Instead, he’s coming at this in perhaps the most patrician way possible. He’s telling voters that while he and the rest of the top tax quintile legislate themselves a massive tax windfall, the layabouts at the bottom of the ladder will get an encouraging pat on the butt and a cheerful, firm reminder that those bootstraps aren’t going to pull themselves up.