Right or wrong, there’s a perception that Illinois politics is a game played best by a well-connected few. This next story won’t improve that image.

Some of the state’s political insiders make big money by lobbying the politicians they help elect. And because of vague disclosure rules, these relationships are not always reported.

By all accounts, Mike Kasper is a brilliant guy and an ace lawyer. He has a lot of powerful friends. And in politics and government, success often boils down to who you know.

“I’m, I’m Mike Kasper. Most of you know my name,” Kasper said at a press conference last winter.

The reporters Kasper was talking to there did know his name, especially after he successfully argued Rahm Emanuel was eligible to run for mayor.

“Have you ever considered living on a permanent basis, anywhere else…other than Chicago?” Kasper asked Emanuel during testimony before an election board hearing officer.

“Never,” Emanuel replied.

Kasper is also top lawyer and treasurer for the Democratic Party of Illinois, and a close ally of its chair, House Speaker Mike Madigan. Kasper used to work full-time for the Illinois House, and still picks up government work - some paid, some unpaid.

One high profile example: a couple years ago, Madigan tapped him to help boot Governor Rod Blagojevich.

“The House prosecutor may now proceed to examine the witness,” directed Illinois Supreme Court Chief Justice Thomas Fitzgerald in the January 2009 proceeding.

“Thank you, your honor, members of the Senate,” Kasper began.

These days, Kasper is defending the favorable political boundaries Democrats drew during redistricting. But his most prosperous association with state government is as a lobbyist.

Kasper’s firm represents Arlington Park Racecourse, lobbying on the recent gambling bill. It also lobbies for ComEd in its push for a new smart-grid, a bill Governor Pat Quinn vetoed, but which may be revived by the legislature this fall.

It’s in lobbying like this that Kasper ends up making use of his government connections, including with lawmakers he’s helped in elections. But it’s not easy for the public to see where those relationships exist.

Campaign legal work only occasionally shows up on campaign finance forms. So some politicians are accepting free legal services from a lawyer who’s also a lobbyist, without disclosing what’s essentially a gift. The director of the state board of elections said that’s because these legal expenses fall into a “gray area” of the law.

Mike Kasper declined to be interviewed for this story, “respectfully,” he said, out of concerns over attorney-client privilege.

I called about a dozen politicians he’s worked for in recent years. Only a handful took my calls, and even fewer would talk on tape. They included state Rep. Monique Davis, a Chicago Democrat.

Kasper worked for Davis in the 2008 election, when he tried to get her opponent disqualified from the race. Campaign finance reports indicate Kasper did not charge for that work, and Mike Madigan’s campaign picked up the tab for miscellaneous costs.

Kasper also worked pro bono for Davis a couple years ago, when she was sued for overdue rent on her Chicago office.

“Mr. Kasper is an excellent attorney,” Davis said. “He’s a very down-to-earth individual. I think he’s the kind of person that anyone could trust.”

We know from interviews and public documents that Kasper has lobbied lawmakers he also did legal work for. Davis said Kasper has never lobbied her, though she said even if he had, there would be no inherent conflict.

“I guess there would be a conflict if one were asking someone to do something that was not legal or ethical,” Davis said. “But I am not aware of any such behavior on my behalf or Mr. Kasper’s behalf.”

“When you’ve got a situation where someone is wearing multiple hats, there are going to be gray areas,” said Kent Redfield, professor emeritus at the University of Illinois at Springfield.

Redfield teaches a course on lobbying, and is a longtime watchdog for these sorts of things. He said there is a potential problem in the intertwining relationships like those Kasper has, and the access and influence that come from them.

“There’s a perception that it’s all kind of one big inside baseball game, and there aren’t any Democrats or Republicans, there’s just people with power, manipulating the system,” Redfield said. “And that’s very corrosive to public support of the political system.”

Redfield says that risk can be addressed by more transparency: require disclosure for all legal work provided to candidates, and make lobbyist reports easily searchable, so the web of relationships is out there for all to see.

To some extent, Mayor Rahm Emanuel has done this at the city level. Using Chicago’s online database, we know Mike Kasper’s firm collects a very healthy six figures from clients to lobby the city.

The city now run by the very mayor he helped elect.