The Clintons and the Carny

Edgar Allen “Ed” Gregory Jr. built a fortune on fairgrounds and midway lights, but his legacy is a blend of crooked carnival games, bank fraud, and a politically explosive brush with the Clinton White House. By the time President Bill Clinton granted clemency to Gregory and his wife, Vonna Jo, in 2000, the couple had already become a case study in how old‑fashioned small‑town grift can intersect with modern Washington influence - and how a carnival magnate could help drag a president’s in‑laws into a pardon scandal.​

Ed Gregory rose to prominence in the traveling amusement business, running one of the country’s better‑known midway operations in the Southeast. Through companies like United Shows of America and Gregory Entertainment, he supplied rides, concessions, and carnival games to state and regional fairs across multiple Southern states, including Tennessee and Alabama. The Gregory outfit became a fixture on the fair circuit, known for large, flashy set‑ups that made it a significant player in what was, by design, a cash‑heavy, barely regulated world.​

Carnival midways have long had a reputation for “crooked” games—concession booths where the odds are quietly tilted, balls are under‑inflated, rims are shaved, or targets are subtly rigged to make winning far harder than it looks. While detailed, itemized case files on every Gregory‑run game are not part of the public record, contemporaneous descriptions of his business emphasize the traditional cash‑intensive, game‑heavy mix that gave carnival operators enormous discretion and opportunity for skimming. It was also common practice for carnival operators to pay off local officials, in the form of contributions, to look the other way when fair-goers complained about rigged games. In that environment, it is not surprising that a man who thrived on the midway would also be comfortable pushing the edge in more formal financial arenas.​

Gregory’s carnival success was substantial enough that he and his wife moved into banking - an unusual but revealing pivot. They gained effective control of a small federally insured bank in Alabama, blurring the lines between their fairground entrepreneurship and conventional finance. That shift set the stage for the criminal case that would eventually require presidential forgiveness.​

In the early 1980s, federal investigators and banking regulators concluded that Gregory and his wife had abused their positions at the Alabama bank. According to later summaries, both Ed and Vonna Jo were charged in connection with bank‑fraud‑related conduct, including misusing bank funds and violating banking laws governing insider loans and transactions. The details fit a familiar pattern from that era’s small‑bank scandals: treating the institution as a personal piggy bank, steering favorable financing to associates and themselves, and ignoring basic safeguards meant to protect depositors and the federal insurance fund.​

The Gregorys ultimately pleaded guilty in federal court. Both received probationary sentences rather than long prison terms, but the convictions put a permanent stain on their reputations and constrained their ability to work in regulated financial institutions. For a time, the case seemed like a localized example of 1980s banking misbehavior - serious, but not particularly newsworthy outside Alabama and the carnival trade.​

Behind the scenes, however, the Gregorys continued to cultivate political connections. Ed Gregory was known in Tennessee political circles, and his carnival business gave him ready access to state‑level power brokers and local officials. The bank fraud case did not end his entrepreneurial life; it simply nudged him back toward the less regulated, more discretionary world of fairs, entertainment, and private deals, where his skills at working relationships remained valuable.​

The story took a dramatic turn in the late 1990s, when Ed Gregory hired Tony Rodham, the younger brother of Hillary Rodham Clinton, as a consultant. Rodham, a sometimes political operative with a string of jobs and ventures, had longstanding struggles to establish a stable career independent of his sister’s rising political profile. For Gregory, bringing Rodham into his orbit offered clear advantages: access to a man whose brother‑in‑law was President of the United States and whose sister was First Lady and soon‑to‑be U.S. Senate candidate from New York.​

According to later reporting and congressional testimony, Gregory paid Rodham hundreds of thousands of dollars over several years. Some of that money was described as consulting fees tied to efforts to expand Gregory’s carnival business overseas, including a 1998 trip that Gregory financed for Rodham to the United Arab Emirates to explore potential fair or entertainment deals there. Other funds were structured as loans, with Gregory or his businesses backing Rodham’s debts.​

Whether these arrangements produced any real economic benefit for Gregory is debatable; the foreign carnival project never materialized into a major, lasting presence in the Gulf. But the relationship clearly bound Gregory and Rodham financially at precisely the moment when Gregory most needed high‑level help: he wanted his federal fraud conviction wiped off the books.​

In March 2000, near the close of Bill Clinton’s second term, the president granted full pardons to Edgar Allen Gregory Jr. and his wife, Vonna Jo, for their 1980s federal bank‑fraud convictions. The U.S. Department of Justice’s Office of the Pardon Attorney had opposed the pardons, arguing that the Gregorys’ conduct and the relatively modest time that had passed since their offenses did not justify such relief. Clinton overrode that recommendation, an action the White House later defended as part of his discretionary constitutional authority.​

What made these two otherwise obscure banking cases politically explosive was the revelation that Tony Rodham had personally lobbied his brother‑in‑law, the president, on the Gregorys’ behalf. In early 2001, as Clinton’s last‑day clemencies came under intense scrutiny in Congress and the press, Rodham acknowledged that he had asked Bill Clinton to pardon Ed and Vonna Jo Gregory, describing them as friends and insisting this was the only clemency request he brought to the president.​

Rodham and the Clintons portrayed the request as a personal favor grounded in the Gregorys’ supposed rehabilitation rather than a paid influence job. Hillary Clinton, facing her new role as U.S. senator from New York, said publicly that her brother had not been compensated to seek the pardon and that the Gregorys were “decent people” who deserved a second chance. But congressional investigators and reporters began to dig into the financial relationship between Rodham and Gregory, and the picture that emerged undercut the idea that this was a simple act of friendship.​

House Government Reform (later Oversight) Committee inquiries found that Ed Gregory and his business interests had, in fact, paid or loaned Tony Rodham around $240,000 over several years in consulting fees and financial support. Some of these loans remained unpaid and were still entangled in Gregory‑related bankruptcy proceedings even after Gregory’s death in 2004. To critics, that looked uncomfortably like a financially dependent in‑law using his proximity to the Oval Office to deliver something of immense value - federal pardons - to a benefactor.​

The committee’s findings did not prove a direct quid pro quo in the strict criminal sense; there was no charge that Gregory had explicitly purchased a pardon. Instead, the picture was one of informal influence: Gregory hired and bankrolled the president’s brother‑in‑law, the brother‑in‑law took his case personally to the president, the Justice Department objected, and the president granted pardons anyway. In Washington’s ethics discourse, that was damning enough.​

The Gregory episode unfolded in parallel with the even more famous Marc Rich pardon and a cluster of other controversial Clinton clemencies that seemed to trace back to donors, friends, or political allies. Together, they fed a narrative that Clinton’s final‑year use of the pardon power was overly influenced by personal relationships, money, and the lobbying of family members - brother Roger Clinton in some cases, brother‑in‑law Hugh Rodham in others, and here, Tony Rodham on behalf of the carnival magnate and his wife.​

For Ed and Vonna Jo Gregory, the practical impact of the Clinton pardons was significant: legally, they were restored to full civil rights with respect to the offenses, their federal bank‑fraud convictions vacated by presidential grace. Symbolically, too, the pardons offered a measure of vindication, allowing supporters to claim they had been overly punished or unfairly stigmatized for their 1980s conduct. Ed Gregory died in 2004, a free man in the eyes of federal law, though the financial and reputational fallout from his cases and the subsequent investigations lingered.​

In the broader Clinton story, however, the Gregory case became one more example trotted out whenever critics discussed “pardon scandals.” The image was powerful: an old‑school midway boss, whose fortune had roots in rigged games and a crooked bank, employing the president’s brother‑in‑law as a globe‑trotting consultant and ultimately receiving a presidential pardon over the objections of career Justice Department officials. It highlighted how relatively small, provincial actors—carnival owners and small‑town bankers—could leverage personal and family connections to reach the very top of American power.​

From the outside, Gregory’s arc looks almost like something out of a political novel. A carnival operator steeped in the culture of “step right up” and tilted odds leverages his money and connections to buy into banking, where he again bends the rules and gets caught. Convicted and constrained but still wealthy and connected, he turns to a new kind of game: influence. Hiring Tony Rodham and sending him abroad on carnival business, Gregory positioned himself so that when the time came, he could ask for - and plausibly expect - help from someone just a phone call away from the president.​

Bill Clinton’s decision to pardon Ed and Vonna Jo Gregory did not, by itself, change the course of American history. But it did offer a revealing glimpse into how the lines between small‑time grift and high politics can blur. The Justice Department said no; a politically connected in‑law said yes; the president sided with family and friends. A pair of bank‑fraud felons who made their money on the midway ended up with one of the rarest prizes in American public life: a presidential pardon.​

In that sense, the Gregory story is less about one couple’s crooked carnival games or one bank fraud case than about the enduring power of access. On the fairgrounds, Ed Gregory knew that the house sets the rules and the marks often never see the mechanism that keeps the odds stacked. In Washington, in the final year of the Clinton presidency, he helped demonstrate that the same principle can apply - quietly but effectively - on the biggest midway of all.

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