> ## Content Index > Fetch the complete content index at: https://www.projectmiddleground.com/llms.txt > Use this file to discover other available public pages before exploring further. # Move the Ball - URL: https://www.projectmiddleground.com/intelligence/move-the-ball/ - Published: 2026-09-08T18:26:18.000Z - Updated: 2026-09-08T18:26:18.000Z - Author: Brad Spirrison Twenty years ago this week, I wrote my first *Tech Matters* column for the then-relatively-flourishing *Chicago Sun-Times*. It profiled [Freshwater Venture](https://web.archive.org/web/20061109193310/http://www.suntimes.com/business/49548%2CCST-FIN-Spir11.article), an effort by Chicago entrepreneurs Eric Antonow and Keith Schacht to map, showcase and water the technology companies already growing here. “The way Chicago will build a richer story is through individuals and the individual success stories,” Antonow told me. Schacht was even more literal. Find promising companies at the embryo stage, add a little water, help them grow. Twenty years later, I keep thinking about the water. Because Chicago has never had a talent problem. **We have a plumbing problem.** Freshwater itself is a useful artifact. Antonow eventually built much of his career in Silicon Valley. Schacht is now in Austin. That is not an indictment of either man. Smart, ambitious people go where ambition has the greatest chance to compound. Marc Andreessen had already supplied the ur-text. Mosaic emerged from the National Center for Supercomputing Applications at the University of Illinois. Andreessen and several colleagues went west, and Netscape helped ignite the commercial Web. Then Chicago generated another remarkable crop. Cleversafe. Fieldglass. Braintree. Grubhub. These were not failures. They were fabulous successes. Chris Gladwin built Cleversafe here using Illinois Tech talent before IBM acquired it for roughly $1.3 billion. SAP acquired Chicago-based Fieldglass. Braintree became one of the world's most important mobile-payment platforms before eBay bought it for roughly $800 million and folded it into PayPal. Grubhub grew from a Chicago startup into a public company before eventually becoming part of Amsterdam-based Just Eat Takeaway and, more recently, Wonder. Again: victories. Founders should sell companies. Investors should make money. Nobody owes his or her hometown permanent ownership of an enterprise. But regions compound differently when some of their winners remain independent long enough to become **the acquirers**. They become anchor customers. Repeat employers. Sources of executive talent. Pools of patient capital. Civic institutions capable of buying the next Cleversafe rather than celebrating when somebody else does. Chicago keeps producing valuable things. Too often, somebody else's balance sheet ultimately captures the value. Call it **value leakage**. Which is particularly maddening because September in Chicago feels like the place the future ought to happen. Lake Michigan is still warm. The air finally quits trying to kill us. The Bears are back carrying that wonderful early-season possibility that this might finally be the beginning of something special. Baseball still contains October. Late summer rolling into early fall is Chicago's spiritual harvest. This is the city that reversed a river, pierced clouds with steel and somehow convinced Michael Jordan that the best way to unleash the greatest individual basketball talent alive was to put him inside Tex Winter's Triangle. That last one matters. The Triangle wasn't designed to make Jordan less Jordan. It was designed so greatness did not depend on one person holding the ball. Move. Create space. Read what is actually happening. Trust the other people on the floor. Put the ball where the opportunity is instead of where hierarchy says it belongs. Phil Jackson and Tex Winter didn't diminish Michael Jordan. They built a system in which Michael Jordan became a six-time champion. **Chicago needs a Triangle.** Because our civic offense remains far too obsessed with who has the ball. Who has the relationship? Who controls the appropriation? Which alderman owns the ward? Which institution owns the grant? Which organization gets to speak for the neighborhood? Who gets the contract? Who gets the credit? That is the modern Chicago Machine. Not merely patronage jobs, cigar-chomping ward bosses or envelopes passed under tables. That version is almost quaint. The Machine today is an operating system: governments, authorities, unions, universities, nonprofits, corporations, consultants and public-private partnerships that too often become more accountable to one another than to the human beings they ostensibly serve. Many lovely people work inside it. That is precisely why it survives. It no longer requires villains. **It runs itself.** And its greatest tax isn't necessarily the one printed on our property-tax bills. It's the friction tax. Time. Permission. Jurisdiction. Meetings. Relationships. Who was consulted. Who wasn't. Who controls the money. Who can stop something. Who can make everybody start the conversation again. Eventually a founder, researcher, artist or investor looks west, south—or increasingly anywhere with broadband and an airport—and asks a perfectly reasonable question: **Why am I doing this to myself?** Later this month, Chicago-born Mellody Hobson and George Lucas will open the Lucas Museum of Narrative Art. In Los Angeles. An institution devoted to nothing less than how human beings tell stories through images. Chicago once had the opportunity to be its home. We managed to puke it out of the lakefront. Nobody involved had to be evil for Chicago to lose. That's the lesson. And now the former U.S. Steel South Works site in **South Chicago, on Chicago's Southeast Side**, is testing whether we've learned it. Illinois is placing an enormous bet there on the Illinois Quantum and Microelectronics Park: frontier technology rising from land that once produced the steel that built the industrial city. This is exactly the kind of bet Chicago should make. But the neighbors are not scenery. **They are stakeholders.** Government can invoke China, national security, technological supremacy, TikTok and the AI bogeyman all day long. None substitutes for answering the person who wants to know what happens to her block, her school, her tax bill, her job prospects and her children. And citizens have obligations here, too. We cannot demand world-class schools, safe streets, research institutions, infrastructure and economic opportunity while accepting opaque performance because: *That's just the way it is.* As Bruce Hornsby tried to warn us: **But don't you believe them.** CPS. CTU. Police. City Hall. City Council. Springfield. Public universities. Private institutions benefiting from public resources. Corporations and nonprofits taking public dollars. Show us the outcomes. Show us the money. Show us who decided. Invite us into the room **before**, not after, the decision. This isn't anti-government, anti-union, anti-business or anti-Chicago. It's the opposite. **We need to gracefully kill the Machine.** Not the people inside it. Not government. Not unions. Not universities. Not corporations or neighborhood organizations. The operating system. The idea that power must remain concentrated, information controlled, relationships intermediated and failure tolerated because that's simply how Chicago works. Humanity is now figuring out how to coexist, for the moment, with machines of our own creation. Quantum and responsible AI give Chicago another almost absurd opportunity to help write the rules of the next era. We already have the championship roster. **Move the ball.** **Run the Triangle.**