O'Boyles' Troubled Past: Financial/Ethics Scandal & Political Bad Acts

Tinley Park, IL March 2025 - Cindy O'Boyle, a candidate for Tinley Park Village Clerk under the Tinley Together party, faces heavy significant scrutiny due to her and her husband Bernie O'Boyle's troubled financial history, business failures, Cook County disclosure fines, and a record of political bad behavior. The O'Boyles have been involved in multiple financial, legal, and ethical issues over the years, raising serious questions about their stability and fitness for public office.

Financial Struggles and Legal Issues: A Troubled Past
The O'Boyles' financial difficulties began with a joint bankruptcy filing, marking the start of a series of financial challenges. Over the years, they faced multiple Federal government tax liens from the IRS, totaling over $75,000. These included liens for $19,438, $7,229, and a substantial $48,931. These liens were eventually released by the IRS, coinciding with the dissolution of two businesses where Cindy served as president. It remains unclear whether these liens were for personal taxes or related to the failed businesses. The release of these liens and the dissolution of businesses suggest a concerted effort to address their financial issues, but it also highlights the extent of their financial struggles.

At one point, Bernie and Cindy refinanced their home, a move that may have been aimed at stabilizing their financial situation. For many homeowners, refinancing is a wise move that can provide lower interest rates and reduced monthly payments, but in the O'Boyles' case it might have been done out of desperation, given their troubled financial history. What's clear is that their financial troubles continue to cast a shadow over their public roles to today. The refinancing and subsequent release of Federal IRS Tax liens indicate a period of significant financial turmoil and troubled debt restructuring for the O'Boyles, and the long-term impact of these actions on their financial stability remains an ongoing point of concern as the ask for public support and trust.

Cindy's Candidacy for Village Clerk: Can She Overcome Her Past?
Cindy O'Boyle's candidacy for Tinley Park Village Clerk is under intense scrutiny due to her financial and legal history. Her campaign, heavily financed and managed by State Representative Bob Rita and State Senator Michael Hastings, raises questions about her ability to manage public funds responsibly and maintain the integrity of the office she seeks. Cindy's financial history, including the dissolution of several businesses and the handling of multiple Federal IRS Tax liens, may influence public perception of her candidacy and fitness for office.

Cindy's campaign is taking place at a time when financial transparency and accountability are increasingly important to voters. Her ability to address and move beyond past financial issues is a critical factor in her campaign, and one that neither she nor her husband Bernie has publicly acknowledged or answered. Their support from influential figures like Bob Rita and Michael Hastings suggests that the O'Boyle's have been loyal and willing cohorts, but it also places them under heavy scrutiny from skeptical citizens. Voters are looking for assurances that Cindy can manage public funds responsibly and maintain the integrity of the office she seeks, despite significance evidence to the contrary.

Bernie's Reelection Woes: A Commissioner Under Fire
Bernie O'Boyle has been reelected twice as a Park District Commissioner, with campaigns notably financed by Hastings and Rita. His tenure has been without highly controversial, as he's failed to file his mandatory Statement of Economic Interest (SEI) on multiple occasions, receiving written notices from the Cook County Clerk warning of consequences including substantial fines and potential removal from office. Despite repeated warnings, Bernie failed to file his SEI again, resulting in fines exceeding $95,000. Facing removal from office, Bernie eventually filed his SEIs only after his failures became public, noting "N/A" across all questions. Bernie has yet to acknowledge his failures or provide any explanation for his bizarre behavior, ignoring multiple written warnings to comply over the course of more than two years. The public is left to speculate whether it was out of deception, arrogance, or simple incompetence. None of these are acceptable answers.

Bernie's repeated failure to file his SEI raises serious questions about his adherence to legal and ethical standards required of public officials. The substantial fines and potential removal from office underscore the severity of these lapses. His actions have not only financial implications but also affect public trust in his ability to fulfill his duties responsibly. The community's response to these issues will be crucial in determining his future in public service, assuming he is not removed from office by the Cook County States Attorney, Will County States Attorney, or the Illinois Attorney General. Bernie faces consequences from all of these offices, as well as over $95,000 in fines. It's unclear whether Bernie must pay those fines personally or could be bailed out by benefactors Hastings and Rita. Based on their histories, it's entirely possible they might abandon both O'Boyles if the become political and financial liabilities.

Harassment and Intimidation: Bernie's Campaign Tactics
Bernie O'Boyle has been caught on home security recordings harassing citizens at their front door on multiple occasions and making false statements. His Tinley Together team has made a practice of visiting and revisiting homes with One Tinley Park yard signs, leaving some Tinley Park citizens feeling intimidated and harassed. During his 2023 campaign, which he won by an embarrassingly small margin of only 28 votes, Bernie told one homeowner that the Park District would never take ownership of the Tinley Park Mental Health Center before the State of Illinois fully remediated all of the polluted land. Bernie was either lying to the homeowner or was not important enough for Hastings and Rita to let him in on the real plans for the property transfer.

Political Conduct & Disturbing the Peace: A Contentious Caucus
Bernie O'Boyle's involvement in the recent Orland Township political caucus further highlights potential issues with political conduct, community relations, personal judgment, and disturbing the peace. O'Boyle participated in a disturbance that required the Orland Park Police to remove O'Boyle and a crowd of about 40 others who were not invited to attend. During the disturbance, Bernie reportedly shouted continually and relentlessly that it was a "public taxpayer event", despite what most attendees acknowledge was a purely political event funded by Orland Democrats, not the Township. Bernie's non-stop screaming also reportedly disrupted the otherwise peaceful and orderly proceedings, shouting incoherently his intentions to "take our village back". Onlookers were apparently quite confused by Bernie's relentless screaming, given it was a Township caucus held in the Village of Orland Park and O'Boyle doesn't live in the Village of Orland Park. Such behavior raises questions about Bernie's judgment and his ability to foster positive community relations.

Melissa Sanfilippo: Tinley Together Team Under Scrutiny
Melissa Sanfilippo, a candidate for Trustee on the same ticket as Cindy, is also part of the Tinley Together party, financed and run by State Senator Michael Hastings and State Representative Bob Rita. Sanfilippo's campaign has faced financial and ethical scrutiny, adding another layer of complexity to the Tinley Together slate. The involvement of Hastings and Rita in financing and running the campaigns raises questions about the influence of state legislators on local elections and the potential for conflicts of interest.

Too Much, Too Far: Can the O'Boyles Gain Public Trust in Time or Ever?
The O'Boyles' financial history and legal issues raise questions about their suitability for public office. While their involvement in public service is undeniable, the recurring financial troubles and legal lapses may impact public trust. Speculation suggests that their financial struggles could influence their decision-making and effectiveness in office. The community's perception of their ability to manage public resources and maintain ethical standards will be a significant factor if they have any hope of earning or holding public roles.

Public trust is a cornerstone of effective governance, and the O'Boyles' financial and legal challenges present a complex narrative for voters to consider. Their ability to address these issues transparently and demonstrate a commitment to ethical standards will be critical in regaining public confidence. The scrutiny they face is a reminder of the high standards expected of public officials and the importance of accountability in public service.

As noted by Kate M. Conlow, an academic economist, "Financial conflicts of interest and ethical lapses can significantly undermine public trust and the effectiveness of governance. Transparency and accountability are essential to maintaining the integrity of public office."

Furthermore, as Upton Sinclair famously stated, "It is difficult to get a man to understand something when his salary depends upon his not understanding it". This quote underscores the potential conflicts of interest that may arise when public officials are financially supported by influential state legislators. The question remains whether Cindy, Bernie, and their Tinley Together teammates serve the local interests of Tinley Park citizens or the broader agendas of their state-level party leaders.

Conclusion: Possible End of O'Boyles' Public Service Journey
Cindy O'Boyle's candidacy for Tinley Park Village Clerk and Bernie O'Boyle's role as a Park District Commissioner are intertwined with significant financial, legal, and ethical challenges. If they decide to continue their political pursuits, the community will watch closely, weighing their past and present troubles against their promises. Their struggles and failings underscore the importance of transparency and accountability for individuals in positions of trust, reminding us that public service is not just about holding office but also about earning and keeping the trust and confidence of the community.