Trump’s One Big Beautiful Bill: What It Really Means for Your Retirement – Milwaukee Financial & Retirement Advisors

Jeremy Keil explores the incoming changes resulting from the “One, Big, Beautiful Bill” and how they might impact your retirement.

Big tax changes are on the horizon—and if you’re nearing or in retirement, you need to pay attention.

On this episode of the Retirement Revealed podcast, I dive into how President Trump’s “One Big, Beautiful Bill” (OBBB) might impact your retirement plan. This legislation brings a mix of permanent, temporary, and eyebrow-raising changes to the tax code, many of which could directly affect your income, deductions, Medicare costs, and charitable giving strategies.

Let’s break down what retirees need to know.

Table of Contents

1. The Myth of “Permanent” Tax Brackets

One of the most buzzworthy changes is the permanence of the current tax brackets. For the past few years, retirees rushed to do Roth conversions before tax rates were scheduled to rise at the end of 2025. But now, those lower rates are considered permanent.

But let’s be honest—permanent in Washington, D.C., doesn’t always mean forever. As Stephen Jarvis of the Retirement Tax Podcast often says, “The tax code is written in pencil, not pen.” So while this may slow the urgency of Roth conversions, the potential for future changes still makes forward-thinking tax planning essential.

2. The New “Senior Bonus” Deduction

Perhaps the biggest headline for retirees is the new “Senior Bonus Deduction.” Starting at age 65, individuals can now claim an additional $6,000 deduction (or $12,000 for couples), regardless of whether they take the standard or itemized deduction.

It’s a valuable benefit—but there’s a catch. This deduction begins to phase out once your modified adjusted gross income hits $75,000 (single) or $150,000 (joint), which could create a hidden marginal tax increase for those over the threshold.

When you add this to the complexity of how Social Security and Medicare costs are calculated, this seemingly simple deduction could actually lead to an unexpected tax bite. I’ll be breaking down how this plays out visually in upcoming videos on my Mr. Retirement YouTube channel.

3. Social Security Taxation: No Change (But Still a Big Deal)

Despite some speculation, the OBBB does not change how Social Security is taxed. Up to 85% of your Social Security income is still taxable depending on your other income levels.

But don’t ignore this just because it’s staying the same. Small changes in income—like selling stock or taking an IRA distribution—can trigger bigger tax bills than you’d expect. That $1 you pull from your traditional IRA might actually lead to $1.85 in taxable income. That’s how you go from the 12% bracket to effectively paying 22%.

4. Bunching Deductions May Be More Important Than Ever

The standard deduction is increasing to $15,750 (single) and $31,500 (joint). This makes it even harder to get a benefit from itemizing deductions like charitable gifts and property taxes.

But don’t give up on deductions yet! “Bunching” strategies—grouping two years’ worth of donations or property tax payments into one tax year—can still be incredibly powerful. And with changes to the SALT (State and Local Tax) deduction cap temporarily increasing from $10,000 to $40,000 between 2025 and 2029, this could create new windows for smart planning.

5. Encouraging Charitable Giving for Everyone

One positive change is the return of the above-the-line charitable deduction for non-itemizers. Starting in 2026, you can now deduct up to $1,000 (single) or $2,000 (joint) for charitable giving even if you don’t itemize—permanently.

It’s not a game-changer, but it might nudge some people to give more, and that’s a win in my book. And for high-income earners in the 37% bracket, charitable deductions are now limited to a 35% benefit—something to consider in your giving strategy.

6. Big Income? Watch for Hidden Tax Traps

If your income is around $500,000–$600,000, pay extra attention. Between the loss of SALT deductions and the standard tax rate, your marginal tax cost could approach 45.5%.

Whether you’re a retiree taking a large IRA withdrawal, selling stock, or a business owner receiving a bonus, planning when and how you receive that income could save you tens of thousands in taxes.

7. Estate Tax and 529 Plan Updates

The estate tax exemption is increasing to $15 million per person (indexed for inflation), so most retirees still don’t need to worry about the “death tax.”

But one area where retirees might get involved is with expanded 529 plan flexibility. More education expenses are eligible, and new “Trump Accounts” are on the horizon. These are retirement-style savings accounts for newborns, funded up to $5,000 per child—no earned income required. If you’re a grandparent who wants to kickstart a child’s retirement, this could be a valuable tool.

Final Thoughts

This tax bill is massive, and we’ve only scratched the surface. But here’s the takeaway: retirement planning isn’t just about how much you have—it’s about how you use it.

Understanding how your income, deductions, and gifting strategies interact with tax law can mean the difference between running out of money or having enough to leave a legacy.

If you want to see how these new changes might affect your retirement plan, reach out to us at Keil Financial Partners or shoot us an email at podcast@keilfp.com.

And be sure to check out our Mr. Retirement YouTube channel for visuals that help you make smarter money decisions.

Because if you know more about your money, you’ll feel better about your money—and make better money decisions.

Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!

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