When Theodore Roosevelt became president in 1901, he quickly established a reputation as a trust buster, railing against the power of giant corporations. In 1902 he ordered a Sherman Act lawsuit aimed at dissolving the Northern Securities Company, the first of 45 antitrust cases pursued during his administration. For the 1904 election, Roosevelt amassed a $2.2 million war chest ($52 million in today’s dollars), mainly by hitting up businessmen who had reason to fear him. The donations included $150,000 from Wall Street banker J.P. Morgan, $100,000 from railroad tycoon George Jay Gould, $125,000 from Standard Oil, and $150,000 from three insurance companies.

When Roosevelt’s Democratic opponent, Alton Parker, claimed corporations were trying to curry the president’s favor by donating heavily to his campaign, the Hero of San Juan Hill called it “a wicked falsehood.” Embarrassed by publicity about his financial support from big business, Roosevelt took up the cause of campaign finance reform, pushing it in his 1905 and 1906 addresses to Congress.

Thus was born the Tillman Act of 1907, which banned corporate contributions to federal campaigns. Nearly a century later, national campaign finance regulation reached its apex thanks largely to another politician determined to prove he was not corrupt.

John McCain was one of five senators who met with federal regulators in 1987 and encouraged them to ease up on the Lincoln Savings and Loan Association, which was under scrutiny for risky investment practices. The taxpayers ended up bailing out the California-based S&L’s federally insured depositors two years later at a cost of $3.4 billion. For his role in the debacle, Lincoln’s chairman, Charles Keating, served more than four years in prison (although his state and federal fraud convictions eventually were reversed because of juror misconduct and faulty jury instructions).

Keating had been the single most important benefactor of McCain’s early political career. Between 1982 and 1987, he had steered $1.4 million in campaign contributions and gifts to the five senators who intervened on his behalf. McCain received $112,000 of that, along with nine trips on Keating’s jets to the Bahamas and elsewhere. In 1991 the Senate Ethics Committee reprimanded the Arizona Republican for his “poor judgment.”

Like his idol Roosevelt, McCain denied any wrongdoing (at least for the first couple of decades; in his 2007 book Hard Call the senator finally admitted to “self-interest” in doing a favor for “an important supporter”). But by his own well-worn account, the Keating Five scandal drove McCain to sponsor legislation aimed at removing the taint of money from politics, an issue that helped define his reputation as a “maverick” and played a conspicuous role in his 2000 campaign for the Republican presidential nomination. “The thing I learned was that it’s not only impropriety that counts,” he said during that campaign. “It’s the appearance that’s just as important.”

Thus was born McCain-Feingold, a.k.a. the Bipartisan Campaign Reform Act of 2002, a law that took Roosevelt’s self-serving crusade a few steps further than the Supreme Court was willing to tolerate. To McCain-Feingold’s supporters, the law’s ban on “electioneering communications”—TV or radio messages sponsored by unions or corporations that mention federal candidates close to an election—was a logical follow-up to the ban on corporate donations championed by Roosevelt.

McCain’s single-minded focus on campaign finance reform won him much applause from journalists, who largely shared his view that money in politics, as he put it in 2001, “affects everything: the tax code, the military, Medicare, Social Security, gambling—you name it.” Yet by 2008, after six years of evidence that McCain-Feingold did not reduce money in politics, McCain was no longer talking about it. When he ran for president against Barack Obama, his own party platform repudiated his signature legislative accomplishment, insisting on “the free-speech right to devote one’s resources to whatever cause or candidate one supports.”

When the Supreme Court struck down McCain-Feingold’s ban on electioneering communications in Citizens United v. Federal Election Commission, the reach of the ruling surprised advocates on both sides of the issue. But it was a foregone conclusion once the Court confronted the implications of letting politicians restrict speech in an effort to avoid the appearance of their own corruption. 

Senior Editor Jacob Sullum (jsullum@reason.com) is a nationally syndicated columnist.