As the Illinois Judicial Inquiry Board investigates powerful Cook County Judge E. Kenneth Wright Jr. for claiming improper property tax exemptions in Will County, a new Injustice Watch examination raises ethical questions about Wright’s Chicago property holdings.The investigation revealed Wright obtained four properties through the estates of his former law clients, sometimes serving as a beneficiary and an executor of the estates. In two cases, records show, his dead former clients filed property tax appeals on property owned by Wright — one more than two decades after the client’s death.Records also show Wright repeatedly failed to disclose ownership in some of his Chicago properties in required ethics statements.And now, two families of his now-deceased former clients have come forward in interviews with Injustice Watch to claim Wright took advantage of his position of trust — in one case, by allegedly engaging in an overly familiar relationship with a law client before she died, and in the other, allegedly betraying the wishes of a longtime friend.“He did this underhanded,” said Deborah Elligan, 75, the daughter-in-law of deceased Wright client Lydia Adams, who signed a will enabling Wright to buy her home at a discount.Wright, 83, declined numerous requests to be interviewed and did not respond to detailed emails outlining the allegations in this report.The loyal Democrat was tapped to become a judge in 1994 and rose to become a highly respected presiding judge overseeing dozens of colleagues in Cook County Circuit Court's First Municipal District. Before joining the judiciary, he was a solo practitioner handling mostly estates.The investigation — which included thousands of pages of land and court records, interviews with surviving relatives of his deceased former law clients, and consultation with legal scholars who suggest the judge may have breached his ethical obligations — revealed how little scrutiny Wright’s background and finances faced as he rose to prominence in the Cook County judiciary. This year — as Wright faced a retention vote in the Nov. 5 election — Injustice Watch flagged his residency conflict during a routine background search for its judicial election guide. The search found Wright had a general homestead exemption on his Joliet ranch house since at least 2005, and another senior citizen tax exemption on that property since 2018.Officials at the Illinois Secretary of State also confirmed Wright’s drivers’ license has listed the same Joliet address since 1977. The Illinois Constitution requires judges to live in the jurisdiction where they serve, and state law allows homeowners to benefit from tax exemptions only on their principal residence.Law professors who examined the facts surrounding how Wright obtained his properties said courts generally prohibit estate lawyers from engaging in business transactions with their clients because such dealings suggest undue influence, financial exploitation or perhaps even fraud.“Anytime an estate planning attorney receives a substantial gift from a client’s will, it raises potential ethical and legal issues,” said Peter Wendel, a law professor at Pepperdine University. “An attorney who engages in such conduct has a lot of explaining to do.”Another Wright client, Elmer Scott, ran a Morgan Park hardware store and owned several South Side properties until his death in 2006 at age 84. During the 1990s, records show Wright represented Scott in property and probate matters. But their friendship — and Wright’s legal advice — continued after Wright became a judge, according to Rose Scott, 79, who is Scott’s widow.Rose Scott said she followed Wright’s guidance because she trusted her former husband’s friend and attorney and was unsure how to assert her rights in court.She said she was shocked to learn Wright took title to her husband’s former home.“People with titles and positions are expected to do right by others, but as soon as his [Elmer Scott’s] eyes were closed, this person starts raking in,” she said.In 2003, Cook County Circuit Court Chief Judge Timothy Evans appointed Wright as the presiding judge of Cook County’s First Municipal District, putting him in charge of more than 40 other judges in Chicago’s housing, evictions and small claims courts.Following Injustice Watch’s initial October report on Wright’s residency conflict, he told leading bar associations his Will County property tax exemptions were inappropriate and he had moved to revoke them. Will County officials confirmed Wright had corrected the record and eliminated the exemptions.The Illinois State Bar Association and the Chicago Bar Association advised a “no” vote for Wright’s retention to the bench, and both groups are now reviewing how they evaluate judges’ performance and fitness for office.The conflict nearly cost Wright his job, but he narrowly won retention in the November election. To read the full Injustice Watch investigation, please go here. David Jackson reports for Injustice Watch, a nonpartisan, not-for-profit journalism organization. Injustice Watch Reporter Kelly Garcia contributed.