"This reeks of hypocrisy," said Richard Pomp, a professor at the University of Connecticut School of Law who focuses on state and local tax laws. "It is not clear why the .com part of the Trump Organisation is not collecting taxes in New York."
The Wall Street Journal reported on Friday that TrumpStore.com collects taxes in Florida and Louisiana, citing the company's website. The site was updated Monday afternoon to add a third state, Virginia. Representatives for the Trump Organisation, which is currently run by the president's sons Donald Trump Jr. and Eric Trump, did not respond to multiple requests for comment.
Amazon has in recent years begun collecting sales tax in all 45 states that require it, as well as the District, as the company opens dozens of distribution centers to keep up with demand for same- and next-day delivery. (Jeffrey P. Bezos, the founder and chief executive of Amazon, also owns The Washington Post.)
Some states, including Indiana, Maine and Ohio, have passed legislation requiring online retailers to collect sales tax regardless of physical presence. The Trump Organisation does not appear to be complying with those laws because it doesn't collect tax for orders sent to those states. Five states - Alaska, Delaware, Montana, New Hampshire and Oregon - do not have a sales tax.
The Supreme Court is preparing to hear oral arguments next week on a case that could overturn a 1992 decision that requires that retailers only collect state and local taxes in places where they have a physical presence. The Trump administration last month filed a brief with the Supreme Court in support of overturning the rule.
"Because of this rule, Amazon was essentially able to have a leg up on all of its smaller competitors for 20 years, during the essential time when it was growing," said Darien Shanske, a professor at the University of California Davis School of Law. "But Amazon is certainly no longer the poster child for not collecting state taxes."
The president in recent weeks has doubled down on his criticism of Amazon, sending shares of the company's stock tumbling as much as 5 per cent in one day. "I have stated my concerns with Amazon long before the Election," Trump tweeted on March 29. "Unlike others, they pay little or no taxes to state & local governments."
Some tax experts say the patchwork rules that currently govern the collection of local taxes do not take into account the new realities of online shopping.
"This, to me, illustrates why [the current laws] are wrong," said Ed Zalinsky, a tax scholar and professor at Yeshiva University's Cardozo Law School. "There is absolutely no reason that Amazon and the Trump Organisation and other international sellers shouldn't be collecting taxes in all states in which they sell."
Other Trump family businesses also collect online sales tax in certain states, but not others. The Ivanka Trump brand, which includes clothing, bedding and shoes, collects sales tax in 31 states in which it or its licensees have a physical presence, according to a person familiar with the arrangement who spoke on the condition of anonymity.
In New York, for example, IvankaTrump.com charges sales tax of $8.70 on a $98 wallet. (The brand also sells its goods on Amazon.com, and allows shoppers to pay for their IvankaTrump.com orders using Amazon Pay.)
Trump Winery, meanwhile, which is overseen by the president's son, Eric, collects sales tax in Virginia, where the winery is located, as well as other states that require it, according to general manager Kerry H. Wollard.
"Trump Winery has always, and will continue to collect, report, and remit sales taxes in jurisdictions where we have an obligation to do so," she said.
