Oct 20, 2026 · 16 min · 10 segments
For decades, the president has claimed charitable deductions on golf courses he never gave away. Now, facing one of the most significant tax bills of his life, he’s pushing the scheme even further—and…
Dan AlexanderGuest
Brittany LewisHost

From 2005 to 2025, Trump donated at least five conservation easements, in all cases forfeiting development rights without surrendering ownership.

including the Jupiter deal, Forbes estimates those gifts could shelter more than $1 billion of income, enough to save an estimated $450 million in taxes.

Obviously, I know you're saying President Trump here is the biggest winner, but who are the winners and losers, if there are any?


And that means that there's less money to go around for the things that the government needs to spend money on.

And then you can also look at the people whose properties are right around these sort of preserved areas.

So, look, if you buy a house on a golf course and the golf course developer says, well, I could actually turn the golf course into 500 more houses.

You want to be able to look out over a nice fairway while you're grilling out your hot dogs in the back of your house.

So if they are forever banned from developing that into other houses, then you benefit from that.

And in fact, the Trump Organization has made this argument before city councils saying, you know, this is really good for the neighbors around the property.

Now, one of the interesting details here is that of the Trump Jupiter course, which is the one that he put a conservation easement over in the end of 2025, one of the neighbors who lives on that course is Eric Trump, who is the president's son.

And another neighbor who has a house on that course is Frank Bisignano, who was appointed in October of 2025, right when the Trump organization was putting together all this easement, to be the CEO of the Internal Revenue Service.


From 2005 to 2025, Trump donated at least five conservation easements, in all cases forfeiting development rights without surrendering ownership.

including the Jupiter deal, Forbes estimates those gifts could shelter more than $1 billion of income, enough to save an estimated $450 million in taxes.

Obviously, I know you're saying President Trump here is the biggest winner, but who are the winners and losers, if there are any?


And that means that there's less money to go around for the things that the government needs to spend money on.

And then you can also look at the people whose properties are right around these sort of preserved areas.

So, look, if you buy a house on a golf course and the golf course developer says, well, I could actually turn the golf course into 500 more houses.

You want to be able to look out over a nice fairway while you're grilling out your hot dogs in the back of your house.

So if they are forever banned from developing that into other houses, then you benefit from that.

And in fact, the Trump Organization has made this argument before city councils saying, you know, this is really good for the neighbors around the property.

Now, one of the interesting details here is that of the Trump Jupiter course, which is the one that he put a conservation easement over in the end of 2025, one of the neighbors who lives on that course is Eric Trump, who is the president's son.

And another neighbor who has a house on that course is Frank Bisignano, who was appointed in October of 2025, right when the Trump organization was putting together all this easement, to be the CEO of the Internal Revenue Service.
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