
Randy Mastro
Former First Deputy Mayor of New York City
47
APPEARANCES
9
PODCASTS
0612
DEC 30
JAN 6
JAN 13
JAN 20
JAN 27
FEB 3
FEB 10
FEB 17
FEB 24
MAR 3
MAR 10
MAR 17
MAR 24
MAR 31
APR 7
APR 14
APR 21
APR 28
MAY 5
MAY 12
MAY 19
MAY 26
JUN 2
JUN 9
JUN 16
JUN 23
JUN 30
JUL 7
JUL 14
JUL 21
JUL 28
AUG 4
AUG 11
AUG 18
AUG 25
SEP 1
SEP 8
SEP 15
SEP 22
SEP 29
OCT 6
OCT 13
OCT 20
OCT 27
NOV 3
NOV 10
NOV 17
NOV 24
DEC 1
DEC 8
DEC 15
DEC 22
DEC 29
JAN 5
JAN 12
JAN 19
JAN 26
FEB 2
FEB 9
FEB 16
FEB 23
MAR 2
MAR 9
MAR 16
MAR 23
MAR 30
APR 6
APR 13
APR 20
APR 27
MAY 4
MAY 11
MAY 18
MAY 25
JUN 1
JUN 8
JUN 15
JUN 22
JUN 29
JUL 6
JUL 13
JUL 20
JUL 27
AUG 3
AUG 10
AUG 17
AUG 24
AUG 31
SEP 7
SEP 14
SEP 21
SEP 28
OCT 5
OCT 12
OCT 19
OCT 26
NOV 2
NOV 9
Nov 6, 2026
Randy Mastro: Next Month Will Be the True Legal Test Legal Test on New York's Controversial Second Home Tax
0:19
0:33
0:42
0:59
1:10
1:22
1:46

Randy MastroGUEST
Well, an appeals court yesterday vacated a judge's ruling that the Mondani administration had to start over because they had so botched the rollout.

Randy MastroGUEST
Not on the merits that the Mondani administration had botched the rollout, but on a legal issue called standing.

Randy MastroGUEST
Because what happened in the case was every time somebody would come forward to be a plaintiff and they joined the lawsuit, the city would immediately say, say, oh, you don't owe the tax because they were trying to avoid the merits of the litigation.

Randy MastroGUEST
And the appellate court found that, therefore, none of my clients had what's in legal terms called a concrete injury since they'd been cleared and don't owe the tax.

Randy MastroGUEST
Well, of course, that's why they sued in the first place, because they were harassed by the city, threatened by the city with owing a pied-à-terre tax that they don't owe.

Randy MastroGUEST
So the ruling is a disappointment because it means that demerits will never be reached, and that's a shame because there are still thousands of New Yorkers being harassed by this administration to pay this tax who don't owe it, who this administration has tried to switch the burden to.
Rita CosbyHOST
laymen who are listening? Does this mean that it's not going, that that aspect is not going for thousands of people? What does that mean?
Cats & Cosby
6:41
6:56
7:14
7:20
7:32
8:08

Randy MastroGUEST
Well, an appeals court yesterday vacated a judge's ruling that the Mondani administration had to start over because they had so botched the rollout.

Randy MastroGUEST
That the Mondani administration had botched the rollout, but on a legal issue called standing, because what happened in the case was every time somebody would come forward to be a plaintiff and they joined the lawsuit, the city would immediately.

Randy MastroGUEST
say, oh, you don't owe the tax because they were trying to avoid the merits of the litigation.

Randy MastroGUEST
And the appellate court found that, therefore, none of my clients had what's in legal terms called a concrete injury since they'd been cleared and don't owe the tax.

Randy MastroGUEST
Well, of course, that's why they sued in the first place, because they were harassed by the city, threatened by the city with owing a pied-à-terre tax that they don't owe.
Rita CosbyHOST
for laymen who are listening? Does this mean that it's not going, that that aspect is not going for thousands of people? What does that mean?
The Cats Roundtable NYC/Local Edition: FBI Assistant Director of NY James Barnacle, Mike LiPetri and More
24:20
24:31
24:40
24:50
24:55

Randy MastroGUEST
Well, John, we are now challenging the constitutionality of that pied-a-terre tax, trying to get rid of it altogether.

Randy MastroGUEST
We won a case that the Mondani administration had botched the rollout and had to do a do-over.

Randy MastroGUEST
And now we are challenging the legality, the constitutionality of that pied-a-terre tax, because it violates the federal and state constitutions.

Randy MastroGUEST
That case was brought out in Suffolk County, and it's going to proceed on an expedited schedule.

Randy MastroGUEST
So by December, we should be in a position to get a ruling whether or not that pied-a-terre tax is wiped out as unconstitutional and illegal.
27:41
How about the other lawsuit that you have where you're fighting the fact that they're freezing the rents and expenses are going up and some of the people that own buildings could go out of business?
Randy Mastro: Taking the Mamdani Administration to Court Over Housing Policies
2:59
3:16
3:40
3:56

Randy MastroGUEST
Under the federal constitution, the governor, state legislators, the mayor admitted at the time this was passed that they were doing this to target out-of-state billionaires who had second homes in New York City.

Randy MastroGUEST
And that is blatantly illegal under the federal constitution, both the Privileges and Immunities Clause, which makes it illegal, unconstitutional to discriminate against out-of-staters, and the Dormant Commerce Clause, which bars states from interfering with interstate commerce.

Randy MastroGUEST
Also, under the state constitution, because, John, they called this a surcharge, even though a tax by any other name would cost people as much.

Randy MastroGUEST
But they did that to try and get around Article 8 of the state constitution, which places a cap on how much of revenue can be raised through real estate taxes.
Sid & Friends Week in Review: John Catsimatidis, Deirdre Imus, Brian Kilmeade
33:48
33:55
34:06
34:19
Sid RosenbergHOST
Do you really feel in your heart of hearts you've got a pretty good case to make this whole thing go away?

Randy MastroGUEST
Oh, I, I think we have a, a great case because the core of the case, federal constitution, the founders, they, they embodied in the constitution you can't discriminate...

Randy MastroGUEST
A state can't discriminate against citizens of another state, and the state can't burden interstate commerce.

Randy MastroGUEST
The intent and effect of the tax is to go after out-of-staters who have a second home in New York City.
The Cats and Cosby Show | 10-01-26
36:31
36:40
36:51

Randy MastroGUEST
Well, that, that's exactly what happened here, right? And now, uh, you know, the response by the city is, is not, you know, to acknowledge that that's what happened.

Randy MastroGUEST
So that's why the city is to say, oh, well, there, there were, you know, there were communications in the Adams administration when, uh, with the Rent Guidelines Board.

Randy MastroGUEST
Communications were the Rent Guidelines Board was independent, it did its own thing, it raised rents even more than the mayor wanted them to raise rents.
Randy Mastro: Today We Have Submitted Documents to Halt Mamdani's Unprecedented Rent Freeze on How Collusive the Process Was
2:56
3:05
3:21

Randy MastroGUEST
Well, that, that's exactly what happened here, right? And now, uh, you know, the response by the city is, is not, you know, to acknowledge that that's what happened.

Randy MastroGUEST
So that's why the city is to say, "Oh, well, there, there were, you know, there were communications in the Adams administration when, uh, with the Rent Guidelines Board." Yeah, guess what the communications were? Communications were the Rent Guidelines Board was independent.

Randy MastroGUEST
It raised rents even more than the mayor wanted them to raise rents, okay? That's how the process is supposed to work.
Cats & Cosby
36:28
36:35
36:44

Randy MastroGUEST
And now, you know, the response by the city is not to acknowledge that that's what happened.

Randy MastroGUEST
So I'm sure the city is to say, oh, well, there were, you know, There were communications in the Adams administration with the Rent Guidelines Board.

Randy MastroGUEST
Yeah, guess what the communications were? Communications were the Rent Guidelines Board was independent.
The Cats and Cosby Show | 09-29-26
2:30
2:55
2:21
Well, Randy Mastro, is it a big victory for New Yorkers? Describe to us what the heck is going on.

Randy MastroGUEST
It is a huge win for New Yorkers, particularly the thousands, indeed hundreds of thousands, who were doxxed by the Mondani administration with threats of a pied-à-terre tax.

Randy MastroGUEST
And that's exactly what the court on Staten Island has now ruled after hearing from the city, multi-hour hearing.
Randy Mastro & Vito Fossella: Breaking News... Mamdani's Second Home Tax Rollout Being Paused is a Huge Win for New York Homeowners
5:28
5:39
6:13

Randy MastroGUEST
the state statute put the burden on the city to make an individualized initial determination who owed the tax and only demand it from people it had determined owed the tax.

Randy MastroGUEST
Instead, the city, whether out of negligence, laziness, or just intentionality to try and ensnare people into having to pay the tax, it switched the burden to taxpayers to prove they live in their own home, as Craig just pointed out, required them to give up their tax returns and other personal information, private information, to try to get an exemption, and if they didn't seek an exemption or didn't get one- They were gonna be deemed to owe the tax when they live in their own homes.

Randy MastroGUEST
So that's why a judge declared all of this illegal and the city has to start over.
Cats & Cosby
2:14
2:39
2:06
Well, Randy Mastro, is it a big victory for New Yorkers? Describe to us what the heck is going on.

Randy MastroGUEST
It is a huge win for New Yorkers, particularly the thousands, indeed hundreds of thousands, who were doxxed by the Mondani administration with threats of a pied-à-terre tax imposition that turned out to be apocryphal.

Randy MastroGUEST
And that's exactly what the court on Staten Island has now ruled after hearing from the city, multi-hour hearing.
Randy Mastro Offers Insight Into Accusations Against Mamdani for Colluding on Rent Freeze Initiative
7:57
8:06
8:22
8:30

Randy MastroGUEST
Well, first of all, from your lips to God's ears, a lot of good things are happening, but cases aren't over until they're over.

Randy MastroGUEST
On the Pieta tear tax, which is called a surcharge, we're waiting for a decision from our judge on Staten Island.

Randy MastroGUEST
And that's the same judge who said there should be a temporary restraining order against the city for their botched rollout.

Randy MastroGUEST
So we remain hopeful that the judge will once again tell the city, hey, you've got to do it over again because you screwed up.
Randy Mastro Is Using the Courtroom to Fight Back Against Madmani's Socialist Policies
6:20
6:31
6:43
6:50

Randy MastroGUEST
Um, you know, uh, um, the governor, uh, who has been, you know, the mayor's sponsor of this bill, um, sh- she did say, "Hey, this has gotta be cleaned up.

Randy MastroGUEST
This has gotta be fixed." And basically the city has now been, because we brought this lawsuit, forced to admit they massively screwed up and sent this to 7,000 people they shouldn't have.

Randy MastroGUEST
Um, but there's more to come because there's gonna be other New Yorkers, you know, who are residents, who never should have gotten these nasty grams.

Randy MastroGUEST
People who own their properties, yeah, in some other form like an LLC or a partnership or a trust.
The Cats Roundtable NYC/Local Edition: Sen. John Fetterman, Rep. Mike Lawler and More
35:45
35:52

Randy MastroGUEST
The Pieta tear surcharge case remains on Staten Island and will be back in court on August 31.

Randy MastroGUEST
And by the way, the city has moved the deadline for applying for exemptions again, this time until October the 6th.
38:35
What did we used to call it in the American Revolution, double taxation without representation? Well, you know,
Randy Mastro: Challenging the Mamdani Administration’s Housing Policies (7 min)
2:43
3:04

Randy MastroGUEST
Uh, it admitted that, you know, it sent threatening notice letters to thousands and thousands of property owners, um, claiming they may owe a surcharge unless they apply for an exemption or else be deemed to owe the tax, that that was just flat out wrong.

Randy MastroGUEST
Uh, and only because of the pendency of this lawsuit, you know, are we where we are now, where the city's feet have been held to the fire.
Randy Mastro: Challenging the Mamdani Administration’s Housing Policies
3:01
3:22

Randy MastroGUEST
It admitted that it sent threatening notice letters to thousands and thousands of property owners claiming they may owe a surcharge unless they apply for an exemption or or else be deemed to owe the tax, that that was just flat-out wrong.

Randy MastroGUEST
And only because of the pendency of this lawsuit are we where we are now, where the city's feet have been held to the fire.
The Cats and Cosby Show | 08-13-26
57:30
57:44
58:02
58:11

Randy MastroGUEST
kind of incredible that that the city isn't owning up to the mistakes it made in rolling out this pied-à-terre surcharge and how badly botched the rollout was.

Randy MastroGUEST
They appealed the judge's TRO order, staying their enforcement of the botched rollout notices, and their filing of an appeal gives them a stay on appeal, even though...

Randy MastroGUEST
In 18 days, we will be back in court on Staten Island for a ruling on the merits that the city broke the law and has to do it over again.

Randy MastroGUEST
So this is going to be resolved, and the city is going to be held accountable, and people are going to get justice here.
Cats and Cosby Team Talk with Vito Fossella & Randy Mastro: Appeal Court Rules NYC Second Home Tax Can Proceed for Now
13:44
13:59
14:17
14:26

Randy MastroGUEST
kind of incredible that the city isn't owning up to the mistakes it made in rolling out this Pierre de Terre surcharge and how badly botched the rollout was.

Randy MastroGUEST
They appealed the judge's TRO order, staying their enforcement of the botched rollout notices, and their filing of an appeal gives them a stay on appeal, even though...

Randy MastroGUEST
In 18 days, we will be back in court on Staten Island for a ruling on the merits that the city broke the law and has to do it over again.

Randy MastroGUEST
So this is going to be resolved, and the city is going to be held accountable, and people are going to get justice here.
Cats and Cosby Team Talk with Vito Fossella & Randy Mastro: Appeal Court Rules NYC Second Home Tax Can Proceed for Now
14:19
14:34
14:52
15:01

Randy MastroGUEST
you know, it's kind of incredible that the city isn't owning up to the mistakes it made in rolling out this pied-a-terre surcharge and how badly botched the rollout was.

Randy MastroGUEST
They appealed the judge's TRO order, staying their enforcement of the botched rollout notices, and their filing of an appeal gives them a stay on appeal, even though...

Randy MastroGUEST
In 18 days, we will be back in court on Staten Island for a ruling on the merits that the city broke the law and has to do it over again.

Randy MastroGUEST
So this is going to be resolved, and the city is going to be held accountable, and people are going to get justice here.
Cats & Cosby
39:56
40:10
40:37
40:53

Randy MastroGUEST
kind of incredible that the city isn't owning up to the mistakes it made in rolling out this surcharge, and how badly botched the rollout was, they appealed.

Randy MastroGUEST
They appealed the judge's TRO order, staying their enforcement of the botched rollout notices, and their filing of an appeal gives them a stay on appeal, even though In 18 days, we will be back in court on Staten Island for a ruling on the merits that the city broke the law and has to do it over again.

Randy MastroGUEST
So this is going to be resolved, and the city is going to be held accountable, and people are going to get justice here.

Randy MastroGUEST
It spread the landscape, 17,000 notice letters, even to me, switching the burden to us to prove we don't owe the surcharge.
The Staten Island Problem - Part 5: Revenge of the Forgotten Borough
8:22
9:29
B
8:12Randy Mastro worked with Giuliani in the US Attorney's office, and later as his first deputy mayor, and he witnessed Molinari's relationship with Giuliani firsthand.

Randy MastroGUEST
A lot of, uh, similarities in backgrounds, Italian Americans, uh, working class family backgrounds, shared a lot of the same values.
B
9:19And while some Staten Islanders were trying to leave the city entirely, Molinari was looking for someone who could remake it in Staten Island's image.

Randy MastroGUEST
I think there's definitely a sense on both their parts about being fair to every borough, and that Manhattan had probably been favored by many prior mayors.
Randy Mastro Speaks on Leading Lawsuit Against Mamdani's Pied-à-Terre Tax
5:58
6:10
6:29
6:47
Sid RosenbergHOST
She said she's wondering if this is a class action suit, and is it too late for people to join this lawsuit? What are the answers to those two questions?

Randy MastroGUEST
It's not a class action, but the ruling... will apply to similarly situated people because the city will have a ruling that the way it rolled out this pied-a-terre tax was not only a fiasco, a debacle, it's illegal.

Randy MastroGUEST
And you know why it's illegal, Sid? Because the state legislation required the city administration in implementing this surcharge to make a determination, an initial determination in the first instance, who's covered by the tax.

Randy MastroGUEST
Instead, this administration sent out 17,000 threatening letters that said, you may be subject to the tax unless you apply for an exemption.
The Cats and Cosby Show | 08-11-26
10:18
10:45
11:14
10:09
Uh, can you give us an update what's happened in the last 24 hours since the big announcement yesterday?

Randy MastroGUEST
Um, we went to court yesterday on behalf of New York City homeowners who showed up on a, a log, a roll filed by the Mondale administration of over 900,000 homeowners, their addresses and their property values, and 17,000 of them who got notice letters, you know, basically threatening them with imposing this second home surcharge.

Randy MastroGUEST
We went into court to say what the Mondale administration did was illegal because instead of following the state law that authorized the imposition of a second home surcharge, uh, and making that determination in the first instance using the information available to it, the Mondale administration shifted the burden to homeowners to have to prove they actually live in their own homes.

Randy MastroGUEST
That state law said you, Mondale administration, have to make the, quote-unquote, "initial determination" and only then do you notify those select few homeowners who are actually subject to a second home surcharge that they may be subject to the charge and should appeal if they disagree.
11:36
Now, i- isn't that what happened in World War II where, where, where, where people were put on notice and, uh, that, uh, they may be guilty of something that they may not even know about?
Randy Mastro: I Am Suing the Mamdani Administration Because the Second Home Tax Violates New York State Law
1:18
1:44
2:13
1:09
Can you give us an update what's happened in the last 24 hours since the big announcement yesterday?

Randy MastroGUEST
We went to court yesterday on behalf of New York City homeowners who showed up on a log a role filed by the Mondani administration of over 900,000 homeowners, their addresses and their property values, and 17,000 of them who got notice letters basically threatening them with imposing this second home surcharge.

Randy MastroGUEST
We went into court to say what the Mondani administration did was illegal because instead of following the state law that authorized the imposition of a second home surcharge and Making that determination in the first instance, using the information available to it, the Mondani administration shifted the burden to homeowners to have to prove they actually live in their own homes.

Randy MastroGUEST
That state law said you, Mondani administration, have to make the quote unquote initial determination.
2:36
isn't that what happened in World War II, where people were put on notice that they may be guilty of something that they may not even know about? And guess what?
Randy Mastro: I Am Suing the Mamdani Administration Because the Second Home Tax Violates New York State Law
2:20
2:46
3:15
2:11
Can you give us an update what's happened in the last 24 hours since the big announcement yesterday?

Randy MastroGUEST
We went to court yesterday on behalf of New York City homeowners who showed up on a log a role filed by the Mondani administration of over 900,000 homeowners, their addresses and their property values, and 17,000 of them who got notice letters basically threatening them with imposing this second home surcharge.

Randy MastroGUEST
We went into court to say what the Mondani administration did was illegal because instead of following the state law that authorized the imposition of a second home surcharge and Making that determination in the first instance, using the information available to it, the Mondani administration shifted the burden to homeowners to have to prove they actually live in their own homes.

Randy MastroGUEST
That state law said you, Mondani administration, have to make the quote unquote initial determination.
3:38
isn't that what happened in World War II, where people were put on notice that they may be guilty of something that they may not even know about?
Scroll for more appearances