President Trump likes to muse about his plans to annex Canada. While proclaiming his love for the Canadian people, he has also threatened the nation with “economic force.” “The only thing that makes sense is for Canada to become our cherished Fifty First State,” Trump wrote on Truth Social last month. “This would make all Tariffs, and everything else, totally disappear.” Some of this talk is probably just trolling; politicians understand the utility of baiting their opponents into outraged arguments. But Canadians seem to be taking Trump seriously. Former Prime Minister Justin Trudeau called Trump’s threats “a real thing” and…

The Internal Revenue Service (IRS) was aware of significant underreporting of cryptocurrency on tax returns and used one of its investigative tools (i.e. a John Doe summons) in 2016 to seek financial information on thousands of individuals, including Mr. James Harper. Harper sued in 2020, alleging unlawful access to his private financial information, and has been embroiled in litigation since then and is now seeking relief from the Supreme Court of the United States. Harper’s case against the IRS has brought significant attention to the issue of financial privacy in the digital age. Harper’s petition to the Supreme Court challenges…

When it comes to estate planning, how you hold property with others can have significant tax implications after you have passed on. Internal Revenue Code Section 2040 governs how joint ownership of property with right of survivorship is treated for federal estate tax purposes. The rules can catch even the most astute investors off guard. Whether it’s a stock portfolio shared between siblings or a family home owned with a spouse, the tax outcome hinges on various factors including who paid what for the asset, whether in the case of spouses both are U.S. citizens and whether there are well-maintained…

As international e-commerce has grown, so too has the complexity of taxing it fairly and effectively. This challenge is particularly acute in the online retail sector, especially in relation to imported low-value goods. Items shipped directly to consumers from abroad often bypass tax collection through de minimis exemptions—thresholds under which goods can enter a country free of duties or taxes. Although these exemptions were originally intended to reduce administrative burdens on customs authorities, they have increasingly been exploited to evade tax and trade rules, particularly amid the surge in low-cost imports from Asia. In response, governments around the world are…

Hola! This week, the newsletter is coming to you from (not so) sunny Spain, where I am attending a law conference. I’m lucky enough to be in Spain during the Copa del Rey, the oldest Spanish football (soccer for those of us in the U.S.) tournament played at a national level. But that’s not the only soccer news happening right now: Real Madrid manager Carlo Ancelotti is defending himself in a Spanish court against charges of tax evasion. Ancelotti is accused of failing to pay over a million euros (US$1.1 million) in Spanish taxes related to image rights. Image rights—the…

The Trump administration’s so-called reciprocal tariffs on countries around the world announced April 2 will raise government revenue in 2025 by $290 billion, or o.95% of GDP, constituting the biggest tax hike since 1982. This is according to calculations by the Tax Foundation. While the U.S. government has claimed that tariffs are a tax on foreign entities, a tariff is paid by the importer, which could in the case of the new tariffs most likely be an American company. Tariffs are then expected to be passed on to that company’s clients and ultimately consumers to offset the importer’s higher cost.…

A severe drop in the stock markets has resulted from the first two days after Trump’s Liberation Day announcement, which imposes significant tariffs on companies bringing goods into the U.S. from other countries. The VIX Index is nearing 5-year highs. These increased costs and volatility are casting a shadow over U.S. stock markets. At 4:00 PM on Apr. 2, President Trump made his Liberation Day announcement, introducing a sweeping set of international tariffs on goods brought into the U.S. While 4:00 PM may seem like an odd time to announce such a large-scale change to foreign economic policy, an alternative…

This week, football (soccer) drama is playing out in Spain both on and off the pitch—one for a chance at glory and another as a top manager defends himself against charges of tax evasion. On the pitch, players have suited up for the Campeonato de España–Copa de Su Majestad el Rey, more commonly known as Copa del Rey. The Copa is the oldest Spanish football tournament played at a national level—and it comes with a significant bonus: the winners qualify for the following season’s Union of European Football Associations (UEFA) Europa League. Off the pitch, Real Madrid manager Carlo Ancelotti…

Lauren Crane is one of the founders of Bender & Crane, a five woman law firm that focuses on divorce. She made it a point to let me know that even though the team is all women, they represent both women and men. We were discussing tax returns and divorce and some of the ways accountants interact with divorce attorneys. Ms. Crane focuses on high income/net worth clients. Her clients live in the State of New York portion of the metro New York City area, mostly in Manhattan. Speaking with her I learned some things that I would never learn…

U.S. tax filers seem to be filing their respective tax forms later this year. Since the IRS started accepting returns in January, the volume has been lower every week compared to the prior year. For those of us who have not yet filed our federal and state tax returns — but are looking for ways to legally keep more of our funds — prospective tax filers might want to consider the “ChatGPT option.” While AI is not a replacement for a tax specialist or accountant, it can help identify documents to wrangle, proper forms to fill out as well as…