While Bruce Rauner was running for governor last year, former DuPage County Board Chairman Bob Schillerstrom endorsed him – hosting a campaign fundraiser that netted $25,000, donating $1,000 from his own political fund and introducing Rauner to other potential backers.

“I was a supporter of the governor early on,” Schillerstrom said in an interview.

Rauner, who won the November election and took office earlier this year, has now become a supporter of Schillerstrom, not only appointing the fellow Republican to the Illinois State Toll Highway Authority board of directors in May, but earlier this month naming him chairman of that panel, which oversees billions of dollars in road projects in northern Illinois and more than 1,500 government jobs.

Was Rauner’s appointment a “thanks” for Schillerstrom’s political help?

No, according to the governor’s office, which released a press release at the time of the appointment saying Schillerstrom’s “experience as the DuPage County Board Chairman will bring a unique perspective to the board. Schillerstrom served three terms with the DuPage County Board. He had a reputation for doing more with less taxpayer money while lowering property taxes. He also held a number of leadership positions within the county and community.”

But Schillerstrom’s appointment could raise questions for another reason: His law firm, Indianapolis-based Ice Miller LLP, has been doing legal work for the tollway since at least 2008. In the past several years alone, the firm has been paid $236,945, according to the tollway.

Ice Miller is involved in two current bond deals that may net the firm another $200,000, according to records and interviews.

Schillerstrom said he’s not directly involved in those deals, and a tollway spokeswoman said Schillerstrom “will forgo any financial participation from Ice Miller’s work on these transactions.”

Schillerstrom initially said he could benefit from the tollway business indirectly – because he’s an equity partner at Ice Miller’s Lisle office sharing in profits from a variety of legal work. He later said he misspoke and won’t benefit from the tollway legal work in any manner.

Either way, Ice Miller will finish the current bond transactions because “leaving now could stop or delay the deals,” Schillerstrom said. But the tollway and Ice Miller have agreed the law firm will not work on future bond sales, so long as Schillerstrom is at the tollway.

“We want to make sure there’s no conflict,” Schillerstrom says. “We recognize that going forward with me on the board we have to change this.”

His law firm was tapped in March to provide legal counsel on the two pending tollway transactions: A $400 million bond sale that will help pay for road projects, including possibly the widening of the Jane Addams Tollway; The refinancing of $350 million worth of bonds, originally issued in 2007 and 2008.

The $400 million deal could close as soon as July, netting the law firm $100,000 in fees, according to the tollway. The other deal could close at any time, and could bring up to $100,000 in fees to Ice Miller.

Schillerstrom, who has been an attorney at Ice Miller since 2004, said he informed Rauner’s staff in advance of the appointment that the firm worked with the tollway.

Ice Miller is part of a rotating pool of 10 firms that provide legal counsel to the tollway on public bond offerings and related debt-issuance counseling, according to the agency.

A four-year contract with Ice Miller expires 2017 but “to avoid future conflicts” Ice Miller and the tollway are going their separate ways, a tollway official said.

Schillerstrom left the DuPage County board in 2010, when he briefly ran in the GOP primary for governor.

Since 2012, Schillerstrom has been a registered lobbyist, with clients that have included an Indiana technology firm and the South Suburban Joint Action Water Agency.

Schillerstrom is stopping his lobbyist activities, saying, “I will not and cannot be a lobbyist if I’m a tollway director.”

Rauner has gone outside Illinois to pick many of his close advisors, as he works to fulfill his promise to “shake up Springfield.”

But Schillerstrom – who was DuPage County chairman for 12 years – can’t claim to be an outsider.

While on the DuPage County board, Schillerstrom drew attention for awarding contracts to Victor Reyes and John Wyma, lobbyists with ties to then-Chicago Mayor Richard M. Daley and ex-Gov. Rod Blagojevich, respectively. And news accounts have noted that Schillerstrom softened his opposition to O’Hare Airport expansion as Ice Miller started winning bond work from Chicago Democrat-controlled government agencies.

Schillerstrom also has deep political ties to Michael Vondra, a controversial businessman once allegedly targeted by Blagojevich for a campaign cash shakedown. Vondra was not accused of wrongdoing.

Meanwhile, Schillerstrom acknowledged in 2010 that he was interviewed by the FBI in the investigation of John Glennon, a former DuPage County lobbyist who was indicted in the federal probe that eventually landed Blagojevich in prison. In 2012, Glennon was sentenced to two years of probation for his role in a kickback scheme. Schillerstrom said he was interviewed as a potential witness, not because he did anything wrong.

As chairman of the tollway’s board – a position most recently held by Paula Wolff – Schillerstrom is paid $36,077 a year and receives health insurance. That’s in addition to his annual pension of $119,640 from the Illinois Municipal Retirement Fund stemming from his DuPage service, according to interviews and records.

This isn’t the first time questions have been raised about one of Rauner’s appointments. The Better Government Association previously reported that a recent appointee to the Illinois Gaming Board – the government agency that regulates gambling across the state – heads a nonprofit that took donations from the state’s most lucrative casino, Rivers in Des Plaines.

This column – a regular feature called The Public Eye, appearing in the Chicago Sun-Times – was written and reported by the Better Government Association’s Andrew Schroedter, who can be reached at aschroedter@bettergov.org or (312) 821-9035.