Though Donald Trump has raised and spent considerably less than many of his Republican rivals in the 2016 election season, Trump has never shied away from injecting money into the political process. Over the last several decades, Trump has spent millions of dollars – as a donor, lobbyist, and activist – to help build and then protect his real estate and business interests.

Trump boasted about the access and influence his money has bought him during the first Republican debate in Cleveland.

"I was a businessman. I give to everybody. When they call, I give," he said. "And do you know what? When I need something from them two years later, three years later, I call them, they are there for me."

Though politicians at various levels have been "there" for him for decades, Trump's success as a donor and influence-peddler has been inconsistent.

Trump's participation in politics began in 1971, after he took control of his father's development firm. To curry favor with the ruling Democratic machine in New York City, Trump donated to mayors and candidates for the city council.

On one occasion, he made a $50,000 loan to a candidate running for council president, only to pay off the loan himself. Trump also dodged the state's contribution limit of $50,000 for individuals and $5,000 for corporations by making payments through eighteen subsidiary companies. In 1985, he made $150,000 in donations to local candidates.

Though Trump was never found to have violated any laws, a report on the city's construction industry determined that “official corruption is part of an environment in which developers and contractors cultivate and seek favors from public officials at all levels.”

After expanding his real estate empire in the 1980s – with the help of mob families located in both New York City and Philadelphia, Trump then turned his sights on Washington in a series of attempts to turn the federal government against his competition.

The law caused Indian casinos to spring up across the country, including along the east coast, which threatened to undermine Trump’s regional dominance.

Trump filed a suit in federal court claiming that the law violated the Tenth Amendment and that it unconstitutionally privileged Native Americans over other citizens, but the case floundered.

Later that year, Trump visited Capitol Hill as Congress considered amending the law. Trump hoped that his access to Democrats – purchased with tens of thousands of dollars in donations to members of Congress, including members of the Senate Indian Affairs Committee – might be instrumental in restricting the growth of Indian casinos.

But Trump’s off-script congressional testimony rankled the panel. Commenting on the owners of the successful Foxwoods Casino in Connecticut, Trump doubted the authenticity of the Mashantucket Pequot Indians. “They don't look like Indians to me," he said. "They don't look like Indians to Indians."

Having failed to curtail the growth of Indian casinos, Trump then lobbied a newly-Republican Congress in 1995 to increase taxes on their earnings. He persuaded Republicans on the House Ways and Means Committee to insert a provision denying Indian casinos an exemption from paying a 34 percent corporate income tax on their profits. Democratic committee members referred to the provision as the “Trump amendment.”

After an unsuccessful fight to stop the construction of an Indian casino in New York (an effort that cost him and his associates $250,000 in legal penalties for undisclosed lobbying in 2000), Trump switched strategies: instead of fighting the growth of such casinos, he decided instead to try to profit from it.

Trump spent approximately $10 million to help the Eastern Pequot tribe – whose reservation neighbors that of the Connecticut tribe that operates Foxwoods – gain tribal recognition from the Bureau of Indian Affairs (BIA). Trump had signed a deal with the smaller Paucatuck faction of the tribe claiming exclusive rights to negotiate the construction of a casino on the tribe’s land.

But in 2002, after the government granted tribal status to the Eastern Pequots, the tribe – led by the larger of the two factions – voted to offer the contract to a rival developer. Trump demanded $500 million from the tribe in lost income in exchange for dropping his lawsuit against the tribe, but he eventually backed down.

Trump's courting of members of both parties shows that Trump has used his wealth largely for financial rather than ideological reasons. By donating to Republicans and Democrats, Trump has ensured that regardless of who holds power, he will have access to key lawmakers.

“It’s not that there’s a quid pro quo," said Roger Stone, a veteran of Richard Nixon and Ronald Reagan's presidential campaigns and a lobbyist who worked for Trump as early as 1980. "But they don’t even listen to you unless you’re a donor."

It is in light of this long history as a Beltway insider that Charlie Black, whose firm once represented Trump, called Trump's anti-Washington populism "ironic."

Nevertheless, even critics of Trump – who claims that members of Congress are "bought and paid for" and said in the Cleveland debate that the "system is broken" – are happy to hear that he seems to have changed his tune, even if Trump attended meetings with powerful donors a month after announcing his candidacy in June.

Trump said in the August debate that he plans to fix the broken system, and he stated later that month on CBS's Face the Nation that donors to his campaign should not expect anything in return -- unless, that is, they are people who "want to see our country be great again."

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