In 2012 and 2013, the campaign spent $31,267 purchasing gifts from the company, which is owned by Reid’s granddaughter, Ryan Elisabeth Reid. All told, she took in nearly seven times more cash than all vendors of donor gifts combined during that period of time.

In 1998, Reid invested $400,000 in an undeveloped residential property located on the outskirts of Las Vegas. Reid’s partner in the deal was attorney Jay Brown, whom Ralston describes as a “master manipulator.” Reid transferred his share of the property to a company Brown controlled in 2001. By transferring the land to Brown’s firm, Reid avoided legal liability and some taxes. But Reid didn’t note the transfer -- or that he had any stake in the company -- in his financial disclosure forms, despite rules requiring such transfers to be reported. By 2004, Brown’s company sold the land, which had been rezoned for a shopping center, and Reid received $1.1 million. He reported the sale as if he had always had control of the property.

When the Associated Press asked Reid about the deal during a 2006 interview, he hung up on the reporter. A spokesman later said that “there were several legal steps associated with the investment during those years that did not alter Senator Reid's actual ownership interest in the land.” However, there was no physical proof that Reid had any stake in Brown’s company. The story may have caused Reid public embarrassment -- he amended his ethics reports to include the full history of the property -- but he walked away from the deal some $700,000 richer.

That isn’t the only problematic land deal Reid was involved with at the time. In 2002, he put $10,000 into a pension fund controlled by another friend, Clair Haycock. The payment gave Reid a sizable parcel of land in Bullhead City, Ariz. According to the Los Angeles Times, Reid purchased the land for one-tenth of its estimated value (and one-fortieth of what it had sold for a decade earlier). Two actions created suspicion afterward. First, Reid sponsored an $18 million earmark for a bridge that would connect Laughlin, Nev., and Bullhead City. This bridge would likely increase property values in the area. Reid also introduced legislation that would benefit Haycock’s lubricant company. Reid aides denied that his support for the earmark or lubricant dealer bill was related to the land purchase. By 2011, Reid’s initial $10,000 investment was valued at between $250,000 and $500,000. The property did not appear in his 2012 disclosure.

While some of Reid’s most lucrative deals involved land, he also benefited from investments in stocks. Near the end of the 2005, he invested between $50,000 and $100,000 in the Dow Jones U.S. Energy Sector Fund, which held shares in several major oil companies. According to National Review, the fund closed at $29.15 on the day Reid purchased. Nearly three years later, in August 2008, Reid sold some of his shares, which closed that day at $41.82. Two months later, Reid-supported legislation that would cost oil companies billions in taxes and regulatory fees passed. The Energy Sector Fund’s shares plummeted to $24.41 each.

While six-figure investments and million-dollar land deals most greatly impact Reid’s wealth, he also manages to save money through some of the perks that come with being the most powerful politician in Nevada (and the U.S. Senate, for that matter).

In 2004 and 2005, for example, he received ringside seats to three boxing matches from the Nevada Athletic Commission. Arizona Sen. John McCain attended one of the fights with Reid and paid $1,400 to reimburse the commission. Reid did not. However, after receiving criticism for accepting the tickets while considering legislation involving the commission, a Reid spokesman said that the senator would no longer be accepting “these kinds of credentials in the future.”

For years, Reid also took part in the bipartisan tradition of riding on corporate jets at a discounted rate. Between 2001 and 2005, he took 35 trips on corporate planes. Ethics rules required him to reimburse the firms -- such as MGM Grand and U.S. Tobacco -- the cost of a first-class plane ticket, which is significantly less than a private jet rental rate. Two years after the Jack Abramoff scandal, the Senate enacted new rules requiring senators to pay prohibitively expensive charter rates to ride on a corporate jet.

While in Washington, Reid stays in a one-bedroom condo he owns at the Ritz-Carlton. Each year, residents contribute money to a holiday bonus fund for Ritz staff. Between 2002 and 2005, Reid spent campaign cash -- not his own money -- to contribute a cumulative total of $3,300 to the holiday fund. His office said that his lawyers had approved the transfers and that a clerical error had prevented them from being properly disclosed. (The explanation was suspect, as several ethics experts said the expenditures clearly violated campaign finance regulations.) Reid reimbursed the campaign and admitted no intentional wrongdoing.

“There is kind of a pattern. He’ll do something pretty bold. There’ll be a lot of publicity about it, and he’ll step back. But then it happens again,” observed Sebelius. “It’s not as if somebody has made a mistake, learned from it … and it never happens again. This keeps happening.”