The New Face of the Old Guard

Bill Conway says he is running for Cook County state’s attorney to “get politics out of the state’s attorney’s office.” He has presented himself as the candidate “who doesn’t owe anyone anything except the people of our county.” Yet Conway’s entire campaign—his donors, his campaign officials, even his close family members—are deeply rooted in Chicago’s old guard. His candidacy is built on a bed of money and influence—and poses significant conflicts of interest.

In terms of funding, Conway’s campaign is almost completely backed by his father, a co-founder of the Carlyle Group, one of the world’s largest investment firms. The elder Conway donated a half-million dollars soon after his son declared his candidacy—and has continued to plow money into the campaign, totalling $4.85 million as of the end of middle of January. Another $195,000 has come from other Carlyle higher-ups. In fact, 86 percent of Conway’s 2019 campaign cash from contributions greater than $1,000 came from Carlyle Group executives or employees.

The Carlyle Group’s three cofounders (left to right): William Conway Jr., Daniel D’Aniello and David Rubenstein

The Carlyle Group, a $222 billion company, is a troubling foundation on which to build a campaign—and a hypocritical choice from the supposed anti-influence candidate. Reportedly founded to “combine capital with politically connected people,” the firm has a scandalous history. In New York, for example, Carlyle employees attempted to corrupt the state’s pension system by using campaign contributions and payments to middlemen to win pensions’ business. In 2009, the company agreed to pay $20 million to settle the scheme.

Meanwhile, Carlyle’s investments have wreaked havoc on the vulnerable. After the firm bought HCR ManorCare, then the second-largest chain of nursing homes in the United States, in 2011, it sucked $1.3 billion out of the company to pay its investors, leaving service at the homes to deteriorate. Because of Carlyle’s leeching, the number of health-code violations in HCR ManorCare facilities reportedly rose 26 percent each year from 2013 to 2017.

Former Mayor Rahm Emanuel has intricate connections to BillConway and the Carlyle Group. (File Photo by Scott Olson/Getty Images)

Of those 2019 Conway donors not affiliated with the Carlyle Group, about a third are longtime supporters of Chicago political players. Conway himself donated $5,400 to former Mayor Rahm Emanuel in 2016. Emanuel is intricately connected to the Carlyle Group: Carlyle employees donated $18,550 to Emanuel’s 2008 congressional campaign, and Emanuel’s new employer, the investment firm Centerview Partners, has done business with the Carlyle Group. Conway’s supporters have also ponied up hundreds of thousands of dollars in support of Emanuel’s mayoral campaigns, and they helped fund the reign of the former Mayor Richard M. Daley, members of his family, and the indicted Alderman Ed Burke.

Lester Crown, Conway donor and controversial billionaire known for Illinois bribery scandal

Old-guard Conway funders include several billionaires. Lester Crown—whose family has owned large stakes in Hilton hotels, Maytag, the Chicago Bulls, and Rockefeller Center—and his wife have so far given $11,600. Crown has been the subject of numerous scandals throughout his life, including giving $23,000 in the 1970s to a fund to bribe Illinois legislators to get higher weight limits on state highways for the trucks in his construction supply business. Billionaire brothers J. Christopher and M. Jude Reyes, co-chairmen of Reyes Holdings, which includes the nation’s largest beer distributor, have also donated to Conway.

Conway’s funders also include Norman Bobins, a retired banker and four-term Chicago Board of Education appointee under Richard Daley. In past cycles, Bobins has given to Emanuel, Daley, Burke, and Illinois House Speaker Michael Madigan. And yet another Conway donor is James “Big Jim” Thompson, a former Republican governor of Illinois and former US attorney appointed by President Nixon, who famously represented his fellow former Illinois Governor George Ryan pro bono when he was facing federal fraud and racketeering charges in the 2000s.

Thomas Anselmo, Conway’s treasurer,
father-in-law and subject of multiple
lawsuits for violations of the FDCP act

Other members of Conway’s circle of backers have their hands deep in Cook County real estate—apparently focused on dominating the market and extracting the earnings of homeowners. One of Conway’s supporters, John Crenshaw, who donated $1,000 to the Conway campaign shortly after it kicked off, works for one of the country’s largest mortgage servicers, Freedom Mortgage Corporation. And Thomas Anselmo, Conway’s campaign treasurer, is a lawyer who has built his career representing creditors and debt-collection agencies, profiting off the debts of Cook County homeowners through foreclosure, eviction, and other default-related actions. Anselmo’s firm has been sued multiple times for violations of the federal Fair Debt Collection Practices Act, which seeks to regulate abusive debt-collecting strategies. Thomas Anselmo also happens to be Conway’s father-in-law.

Conway’s campaign is run by experienced influence-peddlers—people intimately familiar with leveraging politics for their own gain. Trisha Rooney Alden, a previous fundraiser and donor to former Mayor Rahm Emanuel, is the campaign’s chair, and has a rich history in Chicago machine politics. The Emanuel administration wrote a loophole into the contribution ban for city contractors so that donors like Rooney Alden could contribute hundreds of thousands of dollars to the Emanuel campaign even though her record-management company, R4 Services, had a contract with the city. In addition to Conway’s campaign, Rooney Alden now chairs Chicago Victory PAC, an independent campaign committee that raises money from Emanuel allies and could provide it to Conway in 2020. Conway and Alden are also both on the board of A Better Chicago, a nonprofit sponsored by management-consulting company Bain & Company and global law firm Latham & Watkins.

With Conway’s closest supporters mired in scandals that have built vast amounts of wealth for them at the expense of the health, safety, and prosperity of everyday citizens, voters can’t be blamed for being skeptical of where Conway’s loyalties lie.

Conway, The Dilettante

The position of state’s attorney is not simply a title for the privileged dabbler, nor a stepping stone to a higher-profile office for the politically ambitious—it’s an incredibly important management and policy position that requires considerable expertise. For Cook County, the second most populous county in the country, the role of state’s attorney requires a lawyer with a depth of experience in criminal law and a conviction for justice.

While Bill Conway certainly has the bankroll and connection to attempt to buy the state’s attorney position, those may be the only credentials he has for the job. Indeed, Conway, a former assistant state’s attorney, has not held a full-time law-related job since leaving the Cook County State’s Attorney’s Office in 2012.

Conway concedes that his initial decision to become a lawyer wasn’t made in the pursuit of justice.

I kind of had gone to law school on a whim, to be honest with you,

Bill Conway, WLS 890 AM

Pressed on why he wanted to join the state’s attorney’s office after he left law school, Conway cited the fact that he had been “mugged a couple times, as maybe I think everybody has at one time or another, which is unfortunate.” These events “left an impression” on him, though he said that, “in my experience, they’re nothing compared to what most victims go through here, so I don’t want to make too much of it.”

If Conway has shown a passion for anything, it’s been for finance. His personal and professional life has been dominated by it since he was a teenager—far more than his short-lived career in prosecution.

Conway’s interest in business began early, likely influenced by his father, the billionaire  co-founder and recently retired co-CEO of the Carlyle Group, one of the world’s largest investment firms. In his senior year of high school, Conway’s yearbook page quoted Gordon Gekko, the fictional personification of financial greed in the film Wall Street: “Ever wonder why fund managers can’t beat the S & P 500? Because they’re sheep and sheep get slaughtered.”

Conway spent his college breaks interning with PricewaterhouseCoopers, then Merrill Lynch, where he made $7,000 per month as a 21-year-old. He also tried his hand at a dot-com second-hand VHS-sales venture—his only job in his first three years out of college.

After law school, Conway joined the Cook County State’s Attorney’s Office as an assistant state’s attorney. He spent less than half his time at the state’s attorney’s office working on the kind of cases that reflect most of the county’s criminal docket—the cases that are in most need of reform. “In my first few years I worked on [misdemeanor] crimes, narcotics, some violent crime, and some gun cases,” he said. His early work also included traffic-court cases.

Conway quickly veered away from the cases that reflect the bulk of the work for the state’s attorney’s office and found a niche in the office’s public corruption and financial crimes unit, essentially serving as a prosecutorial money man for three and a half years. His personnel file shows he worked on 48 criminal cases between 2007 and 2012. But Conway also spent most of his six years at the state’s attorney’s office working toward an MBA in finance, believing “a career in business might be more to his liking,” according to a 2018 profile of him in The New York Times.

Since he left the state’s attorney’s office in 2012, Conway hasn’t worked a full-time job related to the criminal justice system. In fact, one of the only times he has seemed to pull himself away from his financial and miscellaneous pursuits has been a foray back into law that can only be seen as political. In May 2019, shortly after the Jussie Smollett case hit the media, Conway appeared as the defense attorney for Candace Clark, a woman also facing prosecution for allegedly filing a false police report. He had found the case in a late-April news story, then showed up at the courthouse several weeks later to represent her. He has used the case to hammer home his campaign talking points: Alluding to the similarities to the Smollett case, he has referred to the situation as an example of a “different set of justice for somebody who’s not connected.”

Since graduating from law school, most of Conway’s work has been in finance. He was an investment banker at JP Morgan from 2013 to 2016, working on mergers and acquisitions and debt and equity financing for big companies like Ford and General Motors. And in 2016, he became a finance instructor at DePaul University’s Driehaus College of Business, lecturing on topics such as real estate. And he has pursued various investment ventures—even while employed by the state’s attorney’s office. Conway’s financial pursuits include:

  • A 12.5 percent stake in Luxe Bloom, a Chicago business that imports roses from Ecuador for commercial purposes. The company’s leaders include many high-profile and incredibly wealthy elite, including Shanna Khan, a close friend of Conway’s wife, Brittany, and the daughter of auto parts billionaire and NFL Jacksonville Jaguars owner Shahid Khan, a major Republican donor who gave $1 million to Donald Trump’s inauguration.

    Conway invested in Luxe Bloom when it was founded in early 2013, when the company’s model appeared to rely on the development of a city-backed perishable cargo center at O’Hare International Airport. The project was overseen by the city council’s Committee on Aviation, at the time chaired by then-Alderman Michael Zalewski, whose home federal agents raided as part of a corruption probe last spring. Management of the cargo center was awarded to corporate entities headed by consummate insiders, including Adela Cepeda, a finance bigwig who sat on the board of the Chicago Housing Authority, and Samuel Wm. Sax, a well-known Chicago banking executive and chairman of the Public Building Commission of Chicago. In the 1980s, Sax faced a grand-jury investigation for allegedly misappropriating as much as $200,000 from a collapsed bank he chaired.
  • A stake in Boos Brothers Investments, which buys up North Dakota real-estate projects. Conway’s partners in the investment, members of the Dovolis and the Boosalis families, are related to Conway’s mother. Dean Dovolis and Gus Boosalis got millions of dollars from Petters Company Inc, a $3.65 billion Ponzi scheme that imploded in 2008. A trustee assigned to recover funds from the Ponzi scheme has sued both Dovolis and Boosalis, attempting to recover the millions they received from Petters.
  • A management position at Raputs LLC from 2010, while he was still at the state’s attorney’s office, to 2013. Conway’s father set up the entity—described as a “family-driven investment fund” that focuses on “the underappreciated, low-tech space”—registering it to the address of the Carlyle Group’s Washington, DC, headquarters.
  • A role as an investor in Hyde Park Angels, a Chicago venture-capital firm, beginning in 2012. By 2015, Hyde Park Angels had reached 110 members and had invested $15 million, according to a co-founder. Two directors of Hyde Park Angels and another from one of its partner firms, Hyde Park Venture Partners, were listed as members of a committee put together in 2017 by Mayor Rahm Emanuel and Governor Bruce Rauner to recruit Amazon’s second headquarters. Conway was also an “entrepreneur in residence” with Hyde Park Venture Partners from 2016 to 2017, according to his LinkedIn profile.

Even in recent years, Conway has continued to devote significant time to acquiring investments. In February 2017, he scored a 10-25 percent direct-ownership stake in GrizzlyRock Capital LLC, a Chicago hedge fund that “exists to exploit mispriced securities.” GrizzlyRock’s manager, Kyle Mowery, donated $5,000 to Conway’s campaign in September.

And in 2018, Conway became affiliated with another Chicago venture capital fund, Hubbard Street Capital Partners LLC, which invests mainly in Chicago-area start-ups. According to one of the firm’s managing members, its investments include Maelle, an online cosmetics retailer; TrustToken, a “stablecoin” cryptocurrency backed by US dollars; Peanut Butter, a start-up that offers employer-provided student-loan repayment resources and contribution plans; and Green Thumb Industries, a cannabis-product manufacturer. The company’s managers include Jonathan Glick, whom Conway has known since their college years at the University of Pennsylvania, when they served together on the Undergraduate Assembly. Through the LLC, Conway and Glick have claimed state tax credits on several investments in Chicago-area startups through an Illinois Department of Commerce and Economic Opportunity angel-investment program. In addition to working on Hubbard Street Capital Partners, Conway and Glick organized their own entity, HSCP 3F LLC, in November 2018, with Conway’s father-in-law, Thomas Anselmo, as a registered agent.

While Conway has had financial opportunities through wealthy friends and family and access to seemingly limitless resources, as a businessman, he hasn’t proven to be the most adept. In addition to the failed second-hand video-selling business, in 2018 he tried to start an apparel company called FTXGear. According to an Instagram account for FTXGear, the company was meant to sell “military inspired athletic gear,” with the proceeds going to “help homeless veterans get housing, get jobs, and get the help they need!” Beyond two Instagram posts, there seems to be no publicly available evidence that the company ever got off the ground.

Conway’s campaign has leaned heavily on his service in the military. He joined the US Navy Reserve in 2012, and beginning in August 2017, he served eight months in Qatar, where he led an intelligence team in support of a bombing campaign on drug laboratories in Afghanistan as part of the Trump administration’s expanded aerial-strike strategy. In a disturbing misunderstanding of the role of state’s attorney, Conway has said he would employ the tactics he used to trace Taliban money to fight gun violence in Cook County, failing to provide specific examples of what that could mean.

Clearly, as the son of a billionaire, Conway has taken advantage of his privilege to dabble in many careers—but he has been less than forthright about the scope and number of his many pursuits. In at least one interview since he declared his candidacy, Conway has suggested that he has spent his entire career either working for the Cook County State’s Attorney Office or in the Navy, without acknowledging that he spent much of his career in finance:

I spent my career working in the Cook County State’s Attorney’s Office and in the Navy. And that is who I am. And I’m going to put forth the message of the things I want to do as state’s attorney and what I care about. And I believe that will resonate.

Bill Conway, WLS 890 AM

Without the legal bona fides, Conway leans on his accounting work at the state’s attorney’s office and the Navy Reserve to justify his candidacy. Yet even that background is stretched: While at least one magazine profile has referred to him as an “accountant,” he isn’t actually a CPA, meaning he doesn’t have the legal authority to sign tax and audit records that is granted by a certified public accountant’s license.

And Conway doesn’t make up for his lack of experience and focus with a heightened sense of maturity. His Venmo, a digital payment platform, shows him engaging with friends with a particularly juvenile sense of humor.

On July 22, 2017, after someone sent Conway a payment request for what they described as “sexual favors,” Conway publicly replied: “A bargain considering the level of service.”

On March 27, 2018, an apparent golfing buddy sent him a payment for “tiny balls.”

And on December 3, 2016, when a friend transferred Conway money for a dry-cleaning bill after his child presumably vomited on Conway, the friend wrote that the payment was for “Cleaning up that Cambodian breast milk” (a reference to a Dave Chappelle comedy sketch).

The Trust Fund Candidate


Bill Conway has not been straight with the public. He’s the son of a billionaire: William Conway Jr., net worth $3.5 billion, co-founder of the Carlyle Group, a $222 billion investment firm. However, throughout his campaign, Conway has gone to great lengths to publicly distance himself from that enormous wealth—even while privately reaping its benefits.

In a radio interview, Conway painted a rustic portrait of his childhood upbringing, insinuating that he grew up in a struggling, one-parent household:

I love my dad. He taught me how to throw a baseball. He took me to my first baseball game. He’s been a great father. Although, that said, I was essentially raised by my single mom on the North Side, and certainly love my mom as well. But I will say, I don’t work for my dad’s company.

Bill Conway, WLS 890 AM
This image has an empty alt attribute; its file name is mom.png

Conway’s campaign material has also invoked this “single mom” narrative. His first campaign ad, released as soon as he announced his candidacy on August 8, 2019, features a photo of Conway and his mother—without his father—at one of his graduations.

It’s all a clear distortion of the privileged life Conway has led.

The public record shows that Conway’s parents have shared in the elder William Conway’s wealth like any other billionaire couple. Washington, DC, property records list William and Joanne Conway as married in 1988, when Bill was 10 years old. And news reports, like a June 2019 press release from Catholic University announcing the couple’s $20 million donation to create the Conway School of Nursing, describe them as husband and wife.

For other charitable giving, for more than 20 years, Joanne Conway, with her husband, has had the Bedford Falls Foundation. The foundation shares an address with the Washington, D.C., headquarters of the Carlyle Group, and holds more than $25 million, according to its 2017 tax filings—the most recent available. Joanne Conway made all of the contributions to the foundation that year.

And even absent her husband’s billions, Joanne Conway’s family seems to have means of its own. Some of her relatives are wealthy investors, including two who brought her son into one of their ventures, Boos Brothers Investments.

This image has an empty alt attribute; its file name is seal-transparent.gif

Bill Conway’s charmed upbringing involved attendance at one of the most prestigious private schools in the state, the Latin School of Chicago, where the middle- and high-school tuition is currently more than $36,000 a year. Latin has bred much of Chicago’s business and political elite, including Lisa Madigan, Illinois Attorney General and daughter of Illinois House Speaker Mike Madigan; Chicago Cubs owner William A. Wrigley III; and deceased Chicago Blackhawks owner William Wirtz. Conway served on the Latin School’s board of trustees from at least 2013 to 2016.

The Conway family’s numerous properties further reflect their wealth. In 1995, when Bill Conway was still in high school, his parents purchased a lot at 70 Mile Stretch Road in Biddeford, Maine, upon which they built a beach house. The oceanfront home assesses for nearly $1.7 million, and is currently on the market for $2.5 million. A few years later, they bought an adjacent property, upon which they built what is presumably a large guesthouse. And in 2000, they purchased a 6,700-square-foot mansion overlooking the ocean in Palm Beach, Florida, for $3.8 million. The house, owned through a limited-liability company of which both of Conway’s parents are managers, is currently appraised at over $8.6 million.

This image has an empty alt attribute; its file name is mainehouse.png
This image has an empty alt attribute; its file name is palmbeach.png

But the Conways likely most expensive real-estate acquisition came in 2014, when the elder William gifted Joanne the exclusive $25 million Golden Door Spa in Escondido, California. In 2018, the $10,000-a-week spa went to war to stop plans to build a 2,135-home community nearby. The feud between the developers and the spa hit fever pitch: “Are we willing to allow the Washington, DC, billionaires who own Golden Door to stop desperately needed housing for San Diego’s working families simply to preserve the serenity of a spa for the super wealthy?” asked a vice president of the development company. “Will we let these billionaires use their gang of high-paid lawyers to mislead voters and pretend that their selfish petition is anything other than a multimillion-dollar effort to manipulate our voters in order to protect their own serenity?” The spa ended up forcing a referendum on local officials’ decision to greenlight the development, which will take place in March.

This image has an empty alt attribute; its file name is spa.jpg
The Golden Door Spa, a $25 million gift from Conway’s father to his wife, Joanne.The $10,000/week spa fought to prevent housing development in the area to maintain serenity for its elite guests.

Conway’s parents have also owned several homes in the Washington, DC, area, near the DC headquarters of the Carlyle Group—including Merrywood, the childhood home of Jackie Kennedy, which they purchased in 1999 for around $15 million and sold for $24.5 million in 2005.

Beyond his parents’ many homes and his expensive education, Bill Conway has benefited greatly from his father’s fortune in adulthood.

In 2009, Conway’s father issued him a $300,000 private loan, which he used to pay off the mortgage on a two-bedroom Chicago condo he purchased. The condo, located at 200 W. Grand Avenue, recently sold for $436,000.

And Conway’s father has nearly completely funded Conway’s campaign for state’s attorney. As of this publishing, he has donated $4.85 million to his son’s candidacy. Another $195,000 has come from Carlyle Group higher-ups. Indeed, 86 percent of Conway’s campaign cash from contributions over $1,000 has come from Carlyle Group executives or employees.