What Crain's Chicago Business Got Right (And Wrong) About High-Net-Worth Divorces

Crain's Chicago Business just hosted a roundtable on family law divorces, and as someone who's guided hundreds of high-net-worth Chicago families through this process, I have thoughts.

The discussion touched on important trends we're seeing—increased complexity in asset division, longer timelines, and the emotional toll on families. But there's more to the story that affects you directly if you're facing divorce.

What They Got Right: Complexity Is Skyrocketing

The roundtable correctly identified that divorces are becoming more complex, especially for affluent families. I see this daily in my practice. Twenty years ago, we might have dealt with a house, retirement accounts, and maybe a business. Today? Cryptocurrency portfolios, multiple LLCs, international investments, stock options that haven't vested, and digital assets that didn't exist a decade ago.

This complexity isn't just paperwork—it directly impacts your settlement timeline and costs. What used to take 8-12 months now often stretches to 18-24 months for high-asset cases.

The Reality They Missed: Emotional Preparation

Here's what the roundtable didn't adequately address—the emotional whiplash you'll experience during a complex divorce. I've walked through this with over a thousand clients, and the pattern is predictable:

Month 1-3: Relief mixed with anxiety. You're finally taking action. Month 6-9: Frustration peaks. Discovery feels invasive and endless. Month 12-18: Exhaustion sets in. You question every decision. Month 18+: Clarity returns. You see the finish line.

Knowing this progression helps. When clients understand they're in the "frustration peak" phase, they make better decisions and don't panic-settle.

What's Really Driving Longer Timelines

The roundtable mentioned longer timelines but didn't dig into why. In my experience, three factors dominate:

Digital Asset Discovery: Cryptocurrency, NFTs, and online business ventures are nightmares to track and value. I recently handled a case where we discovered the spouse had $400K in various crypto wallets. Finding them took eight months.

Private Equity and Stock Options: These assets are increasingly common among Chicago's affluent professionals. They're also incredibly difficult to value and divide. Vesting schedules, clawback provisions, and illiquidity issues can add a year to your case.

International Complications: More Chicago families have international ties—overseas accounts, foreign real estate, or businesses with global operations. Each jurisdiction adds months to the process.

The Settlement Strategy That Works

After handling hundreds of high-asset divorces, I've learned this: the families who fare best don't fight over every asset. Instead, they focus on three priorities:

• Liquidity first: Cash and easily liquidated investments for immediate needs
• Income-producing assets second: Rental properties, dividend stocks, business interests that generate ongoing income
• Everything else third: Personal property, collectibles, and sentimental items

This hierarchy prevents you from spending $50K fighting over assets worth $30K—something I see too often.

What This Means for Your Divorce

If you're considering divorce or already in the process, here's what you need to know:

Start financial discovery early: Begin gathering financial documents before you file. The more organized you are upfront, the faster and less expensive your case will be.

Expect the unexpected: In every high-asset case, we discover something the client didn't initially remember or consider significant. It's normal.

Plan for 18-24 months: While some cases resolve faster, planning for a longer timeline reduces stress and helps you make better financial decisions during the process.

Choose expertise over familiarity: Your friend's divorce attorney who handled their straightforward case may not be equipped for cryptocurrency analysis or international asset tracing.

The Bottom Line

The trends discussed in Crain's roundtable are real, but they don't have to derail your divorce. With proper preparation and experienced counsel, even the most complex high-asset divorces can be resolved efficiently and fairly.

The key is understanding what you're facing from day one. Knowledge reduces anxiety, and reduced anxiety leads to better decisions.

If you're dealing with a complex divorce situation, don't wait for problems to compound. The earlier we can start organizing and strategizing, the better your outcome will be.

Written by Jonathan D. Steele

Chicago divorce attorney with cybersecurity certifications (Security+, CEH, ISC2). Illinois Super Lawyers Rising Star 2016-2025.

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For more insights, read our Divorce Decoded blog.