Ask Tim: The True Cost of Being a Las Vegas Raiders Fan

Summer has arrived, which means the calendar is full of camp gear, baseball scores, sunscreen arguments, and at least three family chats with way too many exclamation marks. Somewhere between booking flights and chasing a wiffle ball into the hydrangeas, Washington decided families needed fresh financial puzzles. Some involve babies. Some involve trusts. All involve paperwork, because apparently joy requires a form.

This week, we have two family finance debates with real teeth. First, a grandparent wants to figure out whether the new Trump Account is a better move than a 529. Then, a family with a large estate wants to revisit past gifts after the federal estate exemption moved to $15 million. One question has a baby. The other has four favored children, a fifth child with a legally adventurous hydroponics setup in Humboldt County, and a Raiders problem. Estate planning: come for the tax code, stay for the family lore.

My Grandchild Qualifies for a Trump Account. Is it Better Than a 529?

Dear Tim,

My daughter had a baby in 2025, and I keep hearing that eligible kids may get a $1,000 federal jump start through a Trump Account. I already planned to help with future school costs through a 529, but the new account sounds like it might be the shiny new toy at the family barbecue.

I am trying to be useful, rather than the grandparent who buys a drum set and then leaves. I want the kid to have choices later, but I also want the tax math to work.

Guidance still feels like wet cement. I want to act early, but I would prefer my financial plan has fewer plot twists than a streaming series that ran two seasons too many.

Grandpa With Receipts

Dear Grandpa With Receipts,

A Trump Account can be a helpful extra bucket, but it should serve as a compliment to a 529 rather than replace it. The key driver is purpose: a 529 is built for education, while a Trump Account is closer to a retirement-styled investment account with flashy new qualified expenses that exempts recipients from early withdrawal penalties.

The eligibility mentioned above is strictly for the government pilot contributions. These accounts can still be opened and funded for anyone under the age of 18, with contributions coming from sources such as friends and family, employers, and non-profits organizations.

It’s important to note that the guidance on Trump Accounts can still shift as IRS and Treasury rules take shape, so this should be treated as a planning lane to watch, rather than a single magic answer. That said, the broad idea is clear enough: grab available benefits when eligible, but keep education dollars aimed at the vehicle built for education.

The variables that change the answer are simple, even if the rulebook has fresh ink all over it. Start with how likely the family is to use education funds, whether the family may qualify for state 529 tax breaks, who should keep asset authority, and how much flexibility matters after high school. Also think about grandparent psychology, which is a real planning factor. If you want a clean, visible gift with a long fuse, that matters too.

Here is a simple way to frame it. Say the child gets a $1,000 federal seed and the family adds $1,000 per year for 18 years. At a 6% yearly growth rate, that could reach roughly $34,300 by age 18. A 529 funded with $5,000 per year for 18 years at the same 6% rate could grow to about $154,500. Different tool, different job. These new accounts can offer limited coverage of qualified expenses including education, first home purchase, entrepreneurial pursuits, etc.

The long-term intention for these new accounts is to set a financial foundation for the early adulthood and long-term retirement needs of recipients.

Although you, as the grandparent, are interested in opening the Trump Account for your grandchild - doesn’t mean your account would receive the seed funding on behalf of the child. Your daughter, the grandchild’s parent, likely already filed the required form to open the account and claim the pilot contribution. It’s worthy to be transparent about your intentions if you choose to pursue a trump account and coordinate account opening and funding with your daughter.

A few things to consider as you approach this decision. First, help the parents confirm eligibility and timing for the Trump Account. Second, keep the 529 alive if education funding is a major family goal. Third, pick a family gift rhythm that survives real life: birthday, year-end, tax refund season, or whenever Grandpa feels rich after finding a parking spot near the restaurant.

One thing people miss is that a 529 has escape hatches. Qualified education use is the headline, but current rules also allow certain 529-to-Roth IRA transfers if the account clears key age, transfer, and lifetime-limit tests. That means “extra 529 assets” may have more flexibility than many families assume.

The bottom line: If the child qualifies, the pilot contribution makes the Trump Account a worthy addition to the toolbox. Even better if the new account fulfills other needs and desires as it relates to your gifting goals. However, the 529 may still be the best fit for education-heavy goals. Shiny new account, sturdy old toolbox. A family may need both.

The Estate Exemption Is $15 Million. Should We Unwind Our Old Gifting Plan?

Dear Tim,

A few years back, my spouse and I moved assets into trusts because everyone said the estate exemption could fall. We wanted to get ahead of the rush, protect future growth, and treat our kids fairly. Well, four of the five kids.

The fifth child is currently pursuing what he calls an “agricultural technology venture” in Humboldt County. His mother calls it illegal hydroponics with better lighting than our kitchen. He also roots for the Raiders, and as a lifelong 49ers fan, I feel this creates a character issue that belongs in the estate binder.

The federal exemption is higher, and I am wondering if we got too cute with the gifting plan. Should we pull assets back, change trust terms, pause future gifts, or just pour a drink and leave the binder alone?

- Four-Kid Gifter

Dear Four-Kid Gifter,

Skip the sledgehammer. A higher federal estate exemption means your plan deserves a fresh review, but it rarely means you should tear up a gifting strategy simply because the headline changed. Especially when headlines are static and nobody knows what the future will bring.

The key driver is whether the old gifts still solve a real problem. If they protect growth, add family guardrails, shield assets, or create clarity, they may still earn their keep.

The variables are estate size, asset basis, trust design, family dynamics, state tax exposure, and how much authority you want to keep. The four-child plan also needs care, because unequal gifting can work when it is written clearly and tied to your values. A Humboldt hydroponics empire plus Raiders allegiance may feel self-explanatory at Thanksgiving, but legal papers prefer plain language over side-eye.

This week, I would pull the estate binder, current asset values, cost basis, trust terms, and prior gift tax returns. Ask your estate attorney and tax team to model three paths: keep the trusts as is, adjust terms where allowed, or shift future gifting. Also review whether each child’s share reflects your actual wishes, because resentment grows faster than an untended tomato plant under premium LEDs.

One thing people miss is that today’s numbers are hardly as relevant compared to the values being reconciled when your estate is settled after your passing. This conversation likely changes significantly if you're 45 years old versus 80. Bringing a wealth manager to the table who can help you project the future growth of your balance sheet across registrations, trusts, etc into the future and coordinate with the legal and tax professionals in adequately addressing your needs. Especially if those needs are in the distant future and hard to quantify today.

A high exemption today is often looked at as a gift when viewed under the longer-term lens of regulatory uncertainty. Does it mean it’s something to aggressively shoot for while we have it? Each person’s unique circumstances dictate the answer.

An important note of caution: “unwind” can be a trap word. Many irrevocable gifts are designed to stay outside your reach, and forcing assets back can carry tax, legal, and family costs.

Sometimes the better answer is adding flexibility through trustee powers, swap powers, directed trustee language, powers of appointment, or fresh gifts with better terms.

The bottom line: review the plan, update the math, and resist the urge to reverse years of work because one federal number changed. Big exemptions are helpful. Clean documents are better. Family clarity beats holiday whispers every time.

Send your Ask Tim questions our way, especially the messy ones. If your family tree has tax issues, trust issues, or one Raiders fan too many, it may be time for a real conversation.