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).

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