Trump Keeps Promising Cash on the Campaign Trail—but Has a Poor History of Following Through

Chad de GuzmanWed, October 21, 2026 at 10:31 AM UTC

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U.S. President Donald Trump arrives to speak at a midterm campaign rally at Pitt-Greenville Airport in Greenville, N.C., on Oct. 20, 2026. —Kent Nishimura—AFP/Getty Images (Kent Nishimura—AFP/Getty Images)

Donald Trump is betting that the promise of more money in Americans’ pockets will translate into support at the ballot box. With his approval ratings low and November’s midterms just weeks away, the President has made a series of financial pledges in a bid to preserve Republicans’ majorities in Congress.

At a Kansas rally on Monday, Trump announced that the Administration is offering an $8 billion aid package to help American farmers offset higher diesel costs in the current harvest season. Diesel has remained above $6 per gallon since mid-September, per the American Automobile Association, as oil prices have been pushed up by the war with Iran, which Trump started in late February.

Some rural voters, who helped elect Trump in 2024, have grown disillusioned with him, but he continued to court them in Kansas, adding: “When the Republicans win, we will pass even more funding for our farmers. We love our farmers.”

Several opinion polls show that rising costs of living are top of mind for voters ahead of the elections. Some polls rate the President’s handling of the U.S. economy as very poor. Disenchantment with the current political and economic system has also reached a point where socialism has grown more popular among Americans.

Trump’s efforts to woo voters with offers of cash gained attention in September, when he explicitly promised a Dallas crowd that his Administration would dole out a $5,000 dividend to every American adult if the GOP maintains its majorities in Congress. But with about 240 million adult citizens, the proposal would cost around $1.2 trillion—a gargantuan financial undertaking that even some in his own party questioned how the U.S. could afford. Democrats, meanwhile, called the dividend proposal a vote-buying scheme.

The same month, the Administration promised to refund more than 950,000 Obamacare enrollees in 30 states $500 each for “overcharges” collected by the Biden Administration. Earlier this month, it promised a one-time $90 payment per person to help more than 20 million enrollees pay for their Medicare premiums. Some voters have already reported receiving these payments.

While mentions of these handouts have earned cheers at Trump’s supporter-packed rallies, it is unclear if they will translate to any additional earned votes. Voter turnout in the U.S. is historically lower during midterm and off-year elections, and Trump, in a bid to boost the GOP’s chances, has repeatedly called on his supporters to imagine that he is on the ballot.

It’s also unclear if voters are sold on Trump’s cash-based solutions. For example, a Wall Street Journal poll in September found that 64% of respondents thought Trump’s proposed $5,000 checks were a “bad idea right now.” And even if Republicans won the election, an Economist/YouGov poll from September found that most voters are skeptical that Trump would deliver—and they have good reason to be.

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What happened to Trump’s past cash proposals

Trump has made many big promises, but he hasn’t always kept them.

He has repeatedly floated the idea of giving a $2,000 stimulus check or tax rebate to most Americans, supposedly funded by revenue from the global tariffs he’s imposed throughout his second term. But since making that promise in November 2025, as of this month, such dividends have yet to materialize. TIME has reached out to the White House for comment.

When his on-and-off friend Elon Musk was implementing a cost-cutting initiative across the federal government last year, Trump said he was considering using some of the savings to give Americans cash. “We’re thinking about giving 20% back to the American citizens, and 20% down to pay back debt,” Trump said in February last year. That plan also never materialized.

During his first term, while he was seeking re-election in 2020, Trump promised that his Administration would send $200 discount cards to 33 million older Americans on Medicare to help them pay for prescription drugs. Critics slammed the plan for lack of a clear funding source and how it appeared to be designed just to court voters, but his term eventually ended without distributing those cards and he did not pursue the policy in his second term that began in 2025.

To save Americans in economic freefall during the COVID-19 pandemic, Trump in 2020 promised to get money to them “as quickly as possible.” It also coincided with his campaign for re-election. Eligible adults were able to receive as much as $1,200 as well as $500 per qualifying child. By October that year, the Internal Revenue Service delivered more than 160 million payments totaling over $270 billion. Although he did make good on his promise, the effort did not help Trump’s re-election, however, as he lost the 2020 presidential race to former Vice President Joe Biden.

Trump pours his own cash into election

Trump appears to be ramping up his own political spending to ensure the GOP’s political victory on Nov. 3. “I have spent, or will be spending, over 400 Million Dollars by Election Day,” he posted on Truth Social on Tuesday. “More than 300 Million Dollars has already been spent on Advertising, Direct and Indirect Voter Contact, Rallies, Rally Arenas, Telerallies, Get Out the Vote Programs, Election Integrity, and more.”

Trump’s super political action committee, MAGA Inc., allocated $277 million, a record amount for a second-term President, from the start of September through the first two weeks of October to help the GOP in the midterms, according to the latest Federal Election Commission filings.

The latest filings also show that MAGA Inc. received about $25 million in donations during that period. Some of the biggest donors include Trump-allied billionaire Diane Hendricks, Blackstone CEO Stephen Schwarzman, and casino-resort developer Steve Wynn.

MAGA Inc. has raised about $473 million since Trump’s re-election in 2024.

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Source: “AOL Breaking”