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Interactive Challenge

GuessThe Official

Ten clues. Eight officials. One question: do you know who actually runs Orland Park?

Clue 1 of 10 Easy
The Clue
This official was 26 years old when first elected — the youngest elected official in Orland Park history at the time. They entered office by defeating a 14-year incumbent. More than three decades later, they reached the top office. The only person in village history to hold three different elected positions.
Clue 2 of 10 Medium
The Clue
This official earned a law degree and spent their early career as a prosecutor in the Cook County State's Attorney's Office. They now teach at two universities — Chicago-Kent College of Law and Purdue — while also running their own law firm representing municipalities. They are a leader in Chicago Gaelic Park and leader of a Boy Scout troop. They won their first elected office in 2025.
Clue 3 of 10 Medium
The Clue
This official grew up in Orland Park from 7th grade and has lived there for 40+ years. Before winning their village board seat in 2025 with the widest margin of any trustee candidate in village history (8,279 votes), they served as President of the Orland Park Public Library Board, overseeing a $4 million remodel and keeping the library operating during the COVID-19 pandemic. They were named Mayor Pro Tem upon taking office — acting mayor in the mayor's absence.
Clue 4 of 10 Hard
The Clue
This trustee holds two degrees from Governors State University — a Bachelor of Arts from 1999 and a Master of Science in Management Information Systems from 2001. Their career is entirely in technology: six years as a Business Development Executive at IBM, then Principal Customer Success Leader for IBM's WatsonX AI platform. They grew up visiting grandparents in Orland Park every summer, and became a homeowner there in 2004. Both of their sons attended Carl Sandburg High School.
Clue 5 of 10 Hard
The Clue
This official attended St. Ignatius College Prep in Chicago — one of the city's elite Jesuit high schools — then earned a Bachelor of Science in Accounting from John Carroll University in Ohio (another Jesuit institution). They've been a licensed CPA for approximately 40 years, running their own Orland Park accounting firm with roughly 10 employees. They also teach accounting as an adjunct at Moraine Valley Community College. In September 2024 at a board meeting, they called Labor Day "one of the best socialist holidays of the year" and apologized within 24 hours.
Clue 6 of 10 Medium
The Clue
This trustee has a degree in Communications from Governors State University (earned in 2002) and has been a licensed real estate broker for over 30 years. Before winning her village trustee seat in 2019, she served on the Orland Fire Protection District Board for six years. Her husband is an Orland Park attorney. Both of her daughters attended Carl Sandburg High School and the University of Illinois. She was the Mayor Pro Tem under the previous administration — a position she no longer holds under Mayor Dodge.
Clue 7 of 10 Hard
The Clue
This trustee holds a Bachelor of Science in Thermal and Environmental Engineering AND an MBA in Finance from the University of Chicago Booth School of Business — the same prestigious business school attended by Orland Park's current mayor. They've been an Orland Park resident for over 30 years, a youth basketball coach for the Orland Youth Association, and a volunteer at both Orland Grasslands environmental preserve and the Bridge Teen Center.
Clue 8 of 10 Medium
The Clue
This trustee owns a real estate development company (2nd Avenue Development LLC) and has a background in commodities trading. They hold an MBA from DePaul University. Before winning their village board seat in 2025, they served on the village's Arts and Recreation Committee and coached youth sports at both St. Michael Parish and the Orland Youth Association. Mayor Dodge described them as having "economic chops and creative ideas about economic development."
Clue 9 of 10 Hard
The Clue
This official served in the Illinois Army National Guard — specifically in the 178th Infantry Regiment and the 44th RAOC — reaching the rank of Sergeant. They did this while simultaneously completing an MBA in Finance and Economics at the University of Chicago Booth School of Business. They grew up in Brighton Park on Chicago's southwest side, attended Kelly High School, and worked at a White Castle to pay for college.
Clue 10 of 10 Hard
The Final Clue
This Orland Township trustee — a first-time candidate in 2025 — received the most votes of all 12 candidates in the township trustee race. A local real estate agent, she ran as part of a wave of Arab and Muslim candidates who swept suburban Chicago elections in April 2025, reflecting the community's growing political power in what was once one of Illinois's most reliably conservative suburban townships. Her win was described nationally as part of a generational shift in southwest suburban politics.
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