As we have rolled past Opening Day of the 2025 Major League Baseball season, fans across the country are filled with hope and excitement for the season ahead. With every new season comes the promise of fresh opportunities, big hits, and maybe even a World Series Championship. But while fans are cheering for home runs, there’s another game being played behind the scenes—one that involves taxes, contracts, and the financial side of the sport. Baseball, like any major industry, is not exempt from the complexities of taxation. In fact, the relationship between baseball and taxes is as intricate as a…

Dear President Trump and the Esteemed Members of the Administration, I hope this open letter finds you well, possibly enjoying the March Madness Basketball Tournament, the start of the Major League Baseball season, or finishing up your plans to purchase Greenland, but you are hopefully also pondering the future of tax policy and the economic stability of this great nation. I certainly understand you have a lot going on and the holiday season at year’s end may still seem like a long way away, but for estate planning attorneys, financial advisors, CPAs, and business appraisers—also affectionately known as the “private…

Few things can complicate the otherwise straightforward matter of death quite like family and the possibility of inheritance. More specifically, few things can turn a well-intentioned estate plan into an unexpected legal circus quite like consanguinity—the fancy legal term for blood relations. For most people, the idea of passing on their worldly goods to family seems intuitive. But estate planning attorneys know better. Blood, as it turns out, is not always thicker than a well-drafted trust. Consanguinity is both the backbone of estate law and, quite often, its Achilles’ heel. Legal Inheritance Through Family Ties In estate law, consanguinity determines…

As more Americans take on international roles, stock options have become a key part of the expatriate executive’s compensation package, especially when working for foreign employers. These options offer exciting opportunities to benefit from a company’s growth, but they also come with complex U.S. tax implications that can catch the unwary off guard. Imagine you’re an American executive at a tech startup in London, and your employer offers you stock options as a perk. It’s a chance to share in the company’s success, but what does it mean for your U.S. taxes? The rules differ from those for traditional wages,…

The season has begun! No, not tax season–that opened on January 27, 2025. I’m talking about baseball season. If you’re a regular reader–or you follow me on social media–you know that I love baseball, so of course, I was front and center for Opening Day (my Phillies won in a real nailbiter).I’ve mentioned before that I attribute a lot of my love for baseball to my grandfather. Like many Americans, when my grandfather reached what we would consider “retirement age,” he was still working. In his mid-70s, he would suit up as a security guard and work nights at the…

President Trump and Congressional Republicans have been working throughout 2025 to create a plan to change the federal income tax system. This task is becoming more difficult each week.​ Many Republican lawmakers aim to reduce federal spending by $1.5 to $2.5 trillion over the next ten years, with a likely target around $2 trillion. Reaching this agreement is difficult due to the Republicans’ narrow majority in Congress.​ The House and Senate have significant disagreements. They can’t agree on whether to have one, two, or even three reconciliation bills. There’s also debate on making tax cuts temporary or permanent.​ President Trump…

The federal government must stop issuing paper checks by September 30 in favor of direct deposit, prepaid cards, or other digital payment options. That’s according to an Executive Order signed by President Donald Trump this week. According to the order, using paper checks and money orders results in costs, delays, risks of fraud, lost payments, theft, and inefficiencies. It highlights that, historically, Department of the Treasury checks are 16 times more likely to be reported lost or stolen, returned undeliverable, or altered compared to an electronic funds transfer (EFT). (Earlier this month, a former U.S. Postal Service employee was found…

An IRA to Roth IRA conversion can be a smart move that can help you keep more of your money in retirement. In this article, I’ll explain what a Roth IRA Conversion is, why it can be powerful for high earners, and how it compares to traditional saving. We’ll also look at how this strategy works for a couple nearing retirement, and how it can help them avoid higher taxes and Medicare surcharges later in life. In fact, retirement accounts that have embedded taxes to be paid overstate how much you will get to spend. I wrote this article about…

The Internal Revenue Service (IRS) has a long-standing reputation in the US that is largely negative in nature. A simple internet search of the “IRS reputation” results in articles logging the challenges with timely processing and concerns with the quality of support provided by the agency. These issues, among others, have led many legislators and lobbyists to call for an overhaul of the organization. The Trump Administration has echoed these sentiments and recently initiated efforts to shrink the IRS with a reduction in existing staff and a hiring freeze on new staff. Reports indicate their target is to reduce the…

The Department of Government Efficiency (DOGE) team reportedly wants to use information from the IRS to investigate potential fraud in the Supplemental Nutrition Assistance Program (SNAP, formerly food stamps). Disclosure restrictions may prevent IRS from sharing the data. But prior analysis at the Urban Institute focused on improving tax administration shows that even if IRS did share the data, differences between how taxes and SNAP are administered likely make the data of limited value. Income standards don’t align SNAP benefits are based on monthly family income, which SNAP can already verify using an electronic tool called “The Work Number” .…