In the United States, Republican presidential candidate Donald Trump faces a growing pile of missed payments for rallies and legal bills during his current bid for the presidency, previous campaigns, and in the private sector.

This comes only weeks before the 2024 general election, where he is set to face off against Democratic presidential candidate and US Vice President Kamala Harris, who holds a tight lead in several key polls. A Marist poll out on Wednesday shows her leading the former US president by five points, four points from a Morning Consult poll and four points from an Economist/YouGov poll.

Harris just surpassed $1bn in fundraising and has, in the past three months, raised nearly twice as much as the Trump campaign. The Trump team is experiencing a decline in small-dollar donors, with contributions of $200 or less now making up fewer than a third of donations. At this point in the 2020 election cycle, those contributions accounted for nearly half of all donations, according to an analysis by the Associated Press and Open Secrets, a non-profit organisation based in Washington, DC.

The Trump campaign’s financial challenges are only underscored by the growing list of parties to whom he and the entities he represents owe money.

While campaigns across the political spectrum have occasionally missed payments, including US Senator Bernie Sanders’s presidential campaign in 2016, Trump’s failure to meet payment deadlines stands out due to its long-term pattern.

Unpaid costs at rallies

Trump owes cities across the country for costs associated with staging a rally, including security costs, public safety expenses, allocation of resources and, in some cases, facility rentals.

One of the bills he owes is to the City of Prescott Valley in Arizona. City officials told Al Jazeera that Trump’s campaign has not paid the full costs of his local rally in 2022. The city said it is still owed $25,737.32.

A city spokesperson told Al Jazeera that they had asked the campaign to pay up front for the most recent rally held earlier this month.

This is far from the only outstanding bill the Republican nominee owes in this swing state of Arizona. The city of Mesa invoiced the campaign for an October 2018 rally. Its attorney followed up a few months later, in December, for payment of $64,477.56, but with no success.

“We believe the Trump 2020 campaign should reimburse our city for those taxpayer dollars, and we have invoiced the campaign accordingly,” a spokesperson for the City of Mesa told Al Jazeera.

“Once we learned about the nighttime event at Gateway Airport [in 2018], we took it upon ourselves to implement every measure necessary to secure the area surrounding the airport to keep everyone safe. That included setting up temporary parking infrastructure for over 12,000 people, setting up barricades, setting up temporary lighting and hiring a towing company. The invoice we sent the campaign reflects that,” the spokesperson told Al Jazeera.

The city says the campaign is not legally obligated to pay this invoice.

Mesa’s Mayor John Giles, a Republican, is among several GOP members who have crossed party lines this election cycle to endorse Democratic nominee Harris, including Wyoming’s former US Congresswoman Liz Cheney.

The city of El Paso, Texas, says the Trump campaign still owes it $569,204.63 for a 2019 rally, much of which is supposed to go to the city’s police department, according to invoices obtained by Al Jazeera. In 2020, the city hired a law firm to send notice of these back payments, but their efforts to pressure the campaign have yet to be successful.

“The city continues to seek the payment of these past due expenses, so city taxpayers do not continue to bear the cost,” an El Paso spokesperson told Al Jazeera.

The city of St Cloud, Minnesota told Al Jazeera something similar. The Trump campaign failed to pay an outstanding invoice due earlier this month. The balance, which totals $208,935.17, covers overtime pay for first responders and relocating road construction to accommodate his motorcade for a rally in the city this past July.

The city of Lebanon, Ohio, confirmed to Al Jazeera that an outstanding invoice from 2018 is still unpaid. While the rally took place when Trump was in the White House, the city has yet to receive its payment of $16,191.

The city of Spokane, Washington, told Al Jazeera that the Trump campaign owes it $65,124.69 for a rally in 2016. The unpaid invoice covers a combined 955 overtime hours for members of the city’s police force. Spokane added that two other campaigns from the 2016 presidential cycle have outstanding invoices, including the Hillary Clinton campaign, which owes $2,793.28 and the Sanders campaign, which owes $33,318.73.

Given Trump’s track record, several jurisdictions now require his campaign to pay for services up front, including Asheville, North Carolina and Tucson, Arizona, where his campaign still owes more than $81,000 for a rally in 2016.

A spokesperson for Grand Rapids, Michigan told Al Jazeera the Trump campaign owes the city $32,771.45 for its rally in July. The balance – due by October 23 – includes overtime pay for first responders. The city added that the campaign had paid outstanding balances for other campaign events held there.

Decades overdue

This all comes as former President Trump racks up legal bills for multiple court cases facing him and his campaign, including reportedly a $2m payment to Rudy Giuliani. The former New York mayor and Trump’s former personal lawyer is one of his biggest defenders in numerous court cases where Trump falsely alleged election interference. The since-disbarred lawyer faces legal fees of his own and is required to pay $148m in damages to two Georgia election workers.

In December 2023, Giuliani filed for bankruptcy protection. In July, a New York bankruptcy judge denied the request.

Giuliani did not return Al Jazeera’s request for comment.

Trump has used campaign funds to pay more than $100m in legal fees even as he continues to rack up penalties in his growing list of lost court cases.

Trump has a long history of failing to pay his outstanding invoices even before entering politics. In 2016, a USA Today investigation found 3,500 lawsuits against him over the course of three decades related to unpaid bills and compensation disputes.

Roughly two dozen lawsuits allege the former president’s companies failed to pay overtime or minimum wage to workers, similar to the complaints from cities Al Jazeera spoke to in its reporting that show that Trump’s undue payment in large part covers overtime pay.

As of 2020, Trump still owes contractors, unpaid for decades, involved in the construction and maintenance of the Taj Mahal Hotel in Atlantic City, which opened in 1990. Trump owed $70m to more than 250 contractors, many of whom hired workers of their own to fulfil services ranging from installing plumbing to guardrails. The hotel closed in 2016.

The Trump campaign did not respond to Al Jazeera’s request for comment.