President Trump just did something many other wealthy people in New York have done this year.

He announced that after 73 years as a resident of New York, he officially wants to become a resident of Florida.

As someone who was born in New York City, and who still lives--well, within commuting distance--I'll try not to take offense.

Because I sort of understand. The New York City area has a lot to recommend it. But the taxes here are tough.

Granted, the president didn't specifically say that's why he's leaving. In a series of tweets 10 days ago, he said: 

"despite the fact that I pay millions of dollars in city, state and local taxes each year [to New York], I have been treated very badly by the political leaders of both the city and state. Few have been treated worse."

There's only one problem--something the president surely understands and has steeled himself for: It's not actually quite that easy to get away from New York, legally speaking.

Tweets or no tweets, the main reason wealthy people try to leave New York for states like Florida is to avoid New York income taxes. 

(Florida is one of the few states that has no income tax, estate tax, or inheritance tax.)

As a result, when wealthy people try to depart, New York usually tries to prove they've left in name only. 

Which brings us to the test with the funny name that Trump will almost certainly have to pass for this to work. It's called "the teddy bear test."

As I wrote earlier this year, it's an inquiry that can be quite intrusive about...

"where the taxpayer keeps the items that are most near and dear to him or her. So, where do you keep your sentimental items, your pets and valuables -- maybe even, where do your kids go to school?

And yes, for short: Where do you keep your teddy bear?"

It's true that most taxpayers don't actually have a teddy bear. But according to Bloomberg, tax cases have turned on things like:

  • Where the former CEO of kept his elderly dog, after he ostensibly moved from New York to (no-tax) Texas. A judge ruled that his "move officially took effect in November 2009, when his dog arrived."
  • Where a Kansas pizza maven kept his cat, Checkers. In Kansas, as it turned out, not tax-free Florida. He lost.
  • Where a wealthy executive left his heart: Paris, the courts in New York eventually agreed, after he established how he'd left his wife, given up a big pay package, and legitimately moved to France to be with a long-lost love.

In Trump's case, I can't help noticing that he owns Trump Tower in midtown Manhattan, which seems like it might be more important than a teddy bear. 

Time will tell--probably a lot of time, as this seems like the kind of tax case that winds up taking years to wind its way through the courts.

By the way, it's not the first time a president has changed their home state. President Clinton and then-First Lady Hillary Clinton bought a house in New York in 1999, so she could run for senate there.

No word on where the Clintons keep their teddy bears.