Chicago City Wire

Back in his hometown of Ossining, NY, Jamie Shapiro's father was 7-0 running for judge. Undefeated.

Here in his adopted city of Chicago, by age 59, Shapiro himself was still winless. His record: 0-4, remarkable even in Cook County judicial annals, where lawyers who ardently pursue the security of pedestrian circuit bench slots are seen as tacky, ignominious, even.

But Shapiro, the family court judge who controversially stripped shared custody of an 11 year old boy from a Pilsen mother because she hasn't taken a coronavirus vaccine, adapted.

Once a anti-Machine "progressive," upon entering the Chicago legal scene in the 1990's, he railed against the state's system of electing judges as favoring the politically-connected over "more qualified" outsiders like himself. Living on the city's north side, he courted gay and lesbian groups with promises to discount legislators' intent and to use his discretion to "interpret" laws in ways that would favor their positions.

As state chair of the far-left Independent Voters of Illinois-Independent Precinct Organization (IVI-IPO), Shapiro even dared to slam Barack Obama, then a U.S. Senator, claiming his 2007 endorsements of black candidates Todd Stroger (for Cook County Board President) and Dorothy Tillman (for Chicago Alderman) weren't "principled" but "of political expedience."

"It may be understandable," he told the Chicago Tribune. "But it's not justifiable."

That was then.

In 2018, Shapiro was suddenly successful in his fifth attempt to win election to the bench. He won a six-year term, expiring in 2024.

Two years later, Steve Garrison of Injustice Watch reported that Shapiro was part of a small group of "longtime friends" of south side Chicago Ald. Edward M. Burke (14th), the longest-serving alderman in Chicago history.

Shapiro and Burke had become so close, Garrison reported, that they had become business partners, forming an investment club called "Table of Wisdom LLC."

Burke was indicted in April; federal prosecutors called him "thoroughly corrupt" in a 14 count corruption indictment.

"Bonnie Fitzgerald McGrath"

Shapiro maiden victory in 2018 came, in part, thanks to thousands of dollars in loans from his elderly parents, Sandra and Edwin (who served as Ossining Town Justice from 1980-2011; he died in 2017), who gave their son a campaign budget 15 times that of his top rival.

But he still may have lost if it weren't for Benita Taman, aka “Bonnie Fitzgerald McGrath," who Injustice Watch reported entered Shapiro's 2018 race as a "sham candidate"-- backed by Shapiro's money and with a fake Irish ballot name-- to split female votes that would have gone his top rival, Robin Shoffner, a black woman.

Shapiro, who will earn $212,500 this year as judge, won with 45.6 percent of the vote. McGrath won 16.1 percent, Shoffner 26.6 percent.

Shapiro's political consultant, who Illinois State Board of Elections records show he paid nearly $270,000, denied the report. 

Shapiro attended William & Mary Law School before joining the U.S. Attorney's office in Chicago. In between unsuccessful runs for judge, he ran a criminal defense practice and worked as an arbitrator. 

In 2002, he drew attention for representing Eileen Bakalla, one of the two women who, for nine years, kept the names secret of the two men--James Degorski and Juan Luna-- who committed the 1993 Brown’s Chicken massacre in Palatine.

Shapiro was appointed as a judge in 2007, but ran and lost for the seat in 2008. He was re-appointed in 2009 by the Illinois Supreme Court and served until 2012, when he ran again and lost again.

Also in 2007, he publicly defended then-Illinois Treasurer Alexi Giannoulias over charges his family's bank made loans to criminals, arguing they were irrelevant because banks cannot deny customers based on their criminal history.

“Even if it happened to be true that his family’s bank made loans to alleged crime figures, banks are not allowed discriminate ogasint prospective customers on any basis other than their creditworthiness," he said.

Shapiro once described his job as judge as navigating "various shades of gray."

"I'm not a strict constructionist. The law is various shades of gray. Rarely is the law a black-and-white issue.' When the law is clear, I do follow it—but the law often gives judges discretion, and I interpret the law quite liberally," he told the Windy City Times.