There was a time when the mention of Cook County Circuit Court Clerk Dorothy Brown wasn’t synonymous with questionable ethics and woefully outdated technology.

Even before the most recent string of stories surrounding Brown, her husband and Gov. Pat Quinn’s anti-violence program, Brown was increasingly viewed as an entrenched politician who for years signed off on dubious practices in her office, including taking cash contributions from her own employees.

During the last several months, the Chicago Sun-Times — led by Springfield Bureau Chief Dave McKinney — has detailed a series of events that are as troubling to taxpayers as they should be worrisome to Brown and her husband, Benton Cook. Taxpayer money from Quinn’s $54 million anti-violence program flowed to Cook, who as it turns out is a convicted felon, according to Sun-Times reports, which also revealed a criminal grand jury probe is underway targeting the Chicago Area Project, which employed Cook.

When we first obtained a copy of that subpoena, it was somewhat startling to find it bore Brown’s signature. Her office said an employee penned it, not Brown herself.

“Whether or not there really is a conflict with Dorothy Brown, and the grand jury process — I don’t really think there’s an issue at this point,” Cook County Inspector General Patrick Blanchard said then. “Could there be down the road? Depends on what happens.”

The Sun-Times on Friday revealed a proxy vote from Brown steered some of the cash from the anti-violence program to her husband’s group.

The potential for conflicts here are tripping over each other.

For her part, Brown has offered little more than a sound bite in response to the spate of stories, calling an investigation involving her husband a “political witch hunt.”

Her office asks for questions in writing. It says it isn’t subject to the Illinois Freedom of Information Act.

Through a spokeswoman, Brown has told the Sun-Times she and her husband were not involved in wrongdoing.

There was a time when things were different.

Like so many politicians in Illinois, Brown first appeared on the political scene as a candidate promising reform and a more open government.

Relatively unknown, she made a bid for city treasurer in 1999 against incumbent Miriam Santos, who happened to be under criminal indictment at the time.

Brown, a lawyer and certified public accountant, was the general auditor for the CTA and president of the National Women’s Political Caucus of Greater Chicago, and she was viewed as an independent. She wasn’t tied to the machine and had a different way of doing things.

For instance, she easily could have gone negative against Santos but didn’t, which some believed may have cost her the election. Brown lost by a few percentage points but mopped up in black wards, including in her home 8th ward, where she had a 4-to-1 advantage over Santos.

The day Brown lost, she made an upbeat declaration about her first-time candidacy.

“This isn’t the last you’ve heard of Dorothy Brown,” she told the crowd. “I will be back.”

By November, she was declared to be a “shoo-in” for the Democratic circuit court clerk’s job.

Brown won the nickname “the church lady” because she tapped into a loyal following from black churches.

Brown knocked out the “machine” candidate, Chicago Ald. Patrick Levar, a close ally of then-Cook County Democratic Party Chairman Thomas Lyons.

So by 2000, with the help of the late Squire Lance, a respected political and community organizer, she was elected.

She won the office. And the spoils.

She took over what is today a 2,300-employee office, one of the last true bastions of political patronage in Illinois.

Ethics questions began to arise before she made it through her first four-year term. Employees began to complain they felt pressured to volunteer for Brown’s campaign, to attend fundraisers or to kick in to Brown’s campaign fund.

They also said they felt forced to donate cash to Brown’s annual birthday party. This all happened, mind you, in a post-Gov. George Ryan climate when most politicians recognized the inherent conflict of interest of tapping employees for campaign money — a practice Ryan espoused.

Brown made headlines when employees began complaining about her “Jeans Day” fundraisers, which involve staffers paying cash to wear denim to work on Fridays. Some staffers said they not only felt pressured to fork over the money — anywhere from $3 to $10 — but questioned just where the money went. After insisting the money went for charitable causes and an employee picnic fund, Brown eventually dumped the fundraiser.

“She’s one of those cases of a reformer gone wrong,” longtime Chicago political consultant Don Rose says. “She more or less joined forces with the regulars. She got into the big money and lots of patronage … Dorothy, unfortunately, found that politics is not only public service but privately beneficial.”

Rose says one of the main attractions of the job was the number of patronage jobs. As we’ve learned through the decades, the ability to hand out jobs significantly raises your clout rating.

“The clerk hasn’t had to do that much; it’s a moderate-level professional office, record-keeping basically,” Rose said. “I think you hear the legal community complain. It’s a pretty sloppily run office.”

In 2012, following the election to her fourth term in office, Brown stopped accepting campaign donations from employees.

Today, however, she’s also under scrutiny with her husband following a Better Government Association and FOX32 report that detailed how a donor gave a parcel of land to Cook and Brown for free, which they turned around and sold for $100,000.

Story after story has hit Brown over the years on ethics. While she’s not had success climbing the ladder — losing a 2010 bid for Cook County board president and a 2006 attempt at the mayor’s office — she’s easily kept her position.

Brown most recently fended off a threat by Ald. Ricardo Munoz (22nd), who was seen as the reform candidate.

How did she do it?

“They are out there protecting her. The Burkes, the Berrios’ and the Madigans,” Rose says. “She’s part and parcel of the organization now.”

Sound familiar?