Mesirow's Gary Pattengale Breaks Down Roth IRA Strategies for High Net Worth Investors

• Roth conversions can reduce long-term tax exposure, but timing and execution are key.
• Tax diversification offers flexibility amid shifting tax laws and retirement income needs.
• We believe personalized planning beats blanket advice when managing wealth through retirement.

CHICAGO, June 9, 2025 /PRNewswire/ -- On a recent "Mesirow Monday" radio appearance on WGN's "Your Money Matters" with Jon Hansen, Mesirow Advanced Planning Specialist and Wealth Advisor Gary Pattengale, CFP® outlined the strategic opportunities—and common pitfalls—of Roth accounts and conversions, especially for high net worth individuals focused on long-term wealth optimization.

"Taxes shouldn't be an afterthought in retirement planning," noted Gary. "Done right, tax strategy becomes a powerful tool for control, flexibility, and legacy."

Roth IRAs and Roth 401(k)s, unlike their traditional counterparts, are funded with after-tax dollars but grow—and can be withdrawn—tax-free. They also aren't subject to required minimum distributions (RMDs), making them a key asset in managing future income and taxes.

Gary emphasized the value of tax diversification, holding both Roth and traditional accounts to hedge against future tax rate changes and legislative uncertainty.

While Roth conversions are often promoted as a universal solution, Gary cautioned that they can trigger unintended consequences, including higher Medicare premiums, capital gains, or Social Security taxation. He noted that phased conversions—executed during lower-income years, typically post-retirement but pre-RMD—can offer significant benefits when well-timed.

"Conversions are not all-or-nothing. Precision matters. Modeling matters," he added.

Gary also warned against paying conversion taxes out of the IRA itself:

"The moment you reduce the converted amount to pay taxes, you lose much of the long-term upside."

Mesirow Wealth Management, the firm's founding capability, provides comprehensive financial planning to help clients evaluate complex decisions and align tax strategy with investment, estate, and philanthropic goals.

About Mesirow
Mesirow is an independent, employee-owned financial services firm founded in 1937. Headquartered in Chicago, with offices around the world, we serve clients through a personal, custom approach to reaching financial goals and acting as a force for social good. With capabilities spanning Private Capital & Currency, Capital Markets & Investment Banking, and Advisory Services, we invest in what matters: our clients, our communities and our culture.

Mesirow has been named one of the Best Places to Work in Chicago by Crain's Chicago Business multiple times and is one of Barron's Top 100 RIA firms. To learn more, visit mesirow.com, follow us on LinkedIn and subscribe to Spark, our quarterly newsletter.

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