What High-Net-Worth Executives Need to Know About Divorce in Chicago (From Someone Who's Handled 1000+ Cases)

I just read the latest piece in Crain's about executive divorce, and it reminded me of a conversation I had last week with a CEO who said, "I never thought this would be me."

Here's the thing: I've sat across from hundreds of high-net-worth executives in Chicago who felt exactly the same way. The corner office, the equity packages, the business you built—none of it prepares you for navigating divorce when millions are at stake.

The Reality Check Most Executives Don't See Coming

When you're earning seven figures and have complex compensation structures, divorce isn't just about splitting assets down the middle. It's about protecting your financial future while untangling years of stock options, deferred compensation, business interests, and retirement plans that most divorce attorneys frankly don't understand.

I've seen too many smart executives make costly mistakes because they assumed their regular attorney could handle this, or worse, that they could figure it out themselves.

The Three Biggest Traps I See High-Net-Worth Clients Fall Into

1. Underestimating the Value of Future Compensation That unvested stock option package? It's marital property in Illinois, even if it doesn't vest for three years. I've had clients lose hundreds of thousands because they didn't properly value and protect their equity compensation early in the process.

2. Not Planning for Tax Consequences Splitting a $2 million investment account isn't the same as splitting a $2 million 401(k). The tax implications can cost you 20-40% more than you planned. Every asset transfer needs a tax strategy.

3. Failing to Protect Business Interests If you own part of a business—whether it's the company you founded or partnership interests—your spouse may be entitled to a share of its value, and potentially its future growth. I've seen divorce settlements that gave ex-spouses ongoing claims to business appreciation. Don't let that be you.

What Actually Works: The Strategic Approach

After handling over 1,000 high-net-worth divorces in Chicago, here's what I've learned works:

Start with comprehensive asset discovery. I mean everything—the obvious accounts, but also the executive perks, deferred compensation, stock options, business interests, even that country club membership. You can't protect what you don't identify.

Get expert valuations early. Your business, your stock options, complex investments—these need professional appraisal by people who understand executive compensation structures, not just general business valuation.

Plan for liquidity. You might be worth millions on paper, but if it's all tied up in illiquid investments or unvested stock, how will you fund the settlement? I work with clients to create liquidity strategies that don't force fire sales.

Think beyond the decree. Your divorce settlement needs to account for how you'll actually execute it. Who's refinancing the house? How do you divide retirement accounts without triggering penalties? What happens when those stock options vest next year?

The Question You Should Ask Your Attorney

Here's what I tell every executive who walks into my office: "How many high-net-worth divorces has your attorney actually handled to completion?"

Because there's a huge difference between having wealthy clients and understanding the intricate financial structures that come with executive-level compensation. You need someone who's navigated stock option divisions, business valuations, and complex tax planning in divorce—not just someone who charges high fees.

Your Next Steps

If you're facing divorce as a high-net-worth individual in Chicago, don't wait to get proper legal representation. The decisions you make in the first 60 days often determine your financial outcome.

Every day you delay proper planning is a day your spouse's attorney might be getting ahead of you on asset discovery and strategy.

I've seen this scenario play out hundreds of times. The executives who protect their wealth are the ones who act quickly, strategically, and with the right expertise.

You didn't build your success by leaving things to chance. Don't start now.

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.