Name: Thomas Massie on His Testy Relationship with Donald Trump
Uploaded: 2025-06-24T18:24:23.000Z
Description: Watch the stand-up comedy video 'Thomas Massie on His Testy Relationship with Donald Trump' from Theo Von Clips on Comedy Buff. Published 2025-06-24. Transcript available.

Watch the stand-up comedy video 'Thomas Massie on His Testy Relationship with Donald Trump' from Theo Von Clips on Comedy Buff. Published 2025-06-24. Transcript available.

- Do you think that Trump wants a war in Iran?
- No, I don't.
I actually don't.
And I've talked to him on the phone about this.
When, do you remember there was a general from Iran
called Soleimani who was basically taken out
while he was in Iraq during the first Trump presidency.
- Bring up Soleimani.
- Yeah, there you go.
- Ooh, interesting looking guy.
He almost looks like two different people
put into one head.
- So they took him out when Trump was president.
- Is he a good guy or a bad guy?
- Bad guy.
- Okay.
- Okay, and then, and I'm not here to litigate that,
but Trump was talking about attacking Iran after that.
I think they shot down one of our drones,
and so tensions were escalating,
and the Democrats put a bill on the floor
to say that you can't go,
basically like my bill this time,
says you can't go to war without a vote of Congress.
And I vote, I was one of three Republicans
who voted for that resolution,
but Trump found out I was gonna vote for it,
and he called me up,
and tried to talk me out of voting for it.
- Mm-hmm.
- And in that conversation,
we talked about war with Iran,
and he genuinely, I do believe,
he genuinely didn't want war with Iran.
His argument to me was that if we,
if Congress gave him the authority to threaten them,
that he could keep us out of a war with the threat.
- Oh, I see.
So that's a strategy.
- It is a strategy.
The problem with the strategy, I told him,
was, okay, if I vote to give you that authority
to declare war, or on your own,
- Mm-hmm.
- you know, preemptively...
- How do I know it will happen?
- Well, what if they call your bluff?
- Mm-hmm.
- And then, now we're in a war,
and I don't get a chance to vote on it,
because I just said, we don't need to vote on it.
And he was not happy with that reasoning, but...
- Well, 'cause I guess, I guess his thought would be,
well, if I tell you I'm not gonna do it no matter what,
then why wouldn't you support me, probably?
- Yeah.
But you can't know that he won't.
And by the way, he told me, he said,
"I'm more libertarian than you are."
- Oh, yeah, really?
- Oh, man, Donald Trump is an interesting guy, man.
What an anomaly of a human being, I think, right?
- He is.
There'll never be another person like him,
particularly not one that becomes president.
And I've been on his good side,
and I've been on his bad side,
and it seems like every couple years, it flips.
- Yeah, I saw, didn't you get uninvited
to the picnic or something?
Was that a thing that, was that a real thing that happened?
- That was a real thing that happened.
- A meme about it or something that you got uninvited to the...
At the last minute, I got re-invited.
But this goes back to 2020, during COVID.
I was the only one who said we're, you know,
this CARES Act is going to bankrupt the country.
Basically, it's going to cause massive inflation and shortages.
So I opposed that.
And the president called me, he was upset with me,
that I would force Congress to return during COVID and vote.
And basically, all I said was, look, this was during COVID.
They wanted to spend $2 trillion by unanimous consent.
I said, if truckers have to work and farmers have to work
and nurses have to work,
why doesn't Congress show up and vote on this?
- Yeah.
- So at the time, he called me a third-rate grandstander
and said I should be thrown out of Congress.
The media immediately descended on me and said,
what did I have to say for myself?
Because he was tweeting all of this.
And they said, well, I'm at least second-rate.
Come on.
- Yeah, help me out here.
- Two years later, he endorsed me for a re-election.
And then, most recently, Bobby Kennedy joined a coalition
with the president for Maha, Make America Healthy Again.
And you can do that through the National Institute of Health
and FDA and CDC and all that.
But also, our food supply is a big, important part of that.
So Bobby Kennedy was advocating for me
to be the Secretary of Agriculture.
And he and I have been talking about it for weeks.
This was before Trump won the election last fall.
- And there's a lot of agriculture out of Kentucky.
That would have been great.
- It would have been great.
- Would it have been something you were interested in?
- Yes, definitely.
'Cause I think there are a lot of things we could do
to basically reinvigorate and empower small farmers
to make healthy food and grow local economies,
things like that.
And so I was all in.
And Bobby Kennedy's team spent a lot of time on it.
And I told him, this was like in October
before the election, I said,
I think there's one problem with your plan.
And he said, what's that?
And I said, I've not endorsed Trump.
And he said, well, it sounds like you need to endorse Trump.
- Do you think that was a strategy
or do you think that it was--
- No, he was genuine.
- Yeah, I would think so.
- And I agreed with him.
So I said, well, how do we announce it?
And he said, we'll come out to Wisconsin Tuesday.
And Tulsi and I are doing this rally
and just come up on stage and announce it there.
And I'm thinking, man, I don't wanna go to Wisconsin
in October to do this.
'Cause I had a lot of other things on my plate at that time.
And so I put it off for a day.
I did look at plane tickets to go to Wisconsin.
I typed out an endorsement of Trump on my iPhone,
read it back to myself.
And I woke up the next morning,
and I thought, this is the day, I gotta do this.
So Trump, when my wife passed away last summer,
he had left a very nice message.
I would have obviously taken his call,
but I was inundated with calls,
but he left a really nice message of condolences.
- That was thoughtful of him.
- And so it was, and that's a side people don't see, right?
I actually campaigned for Ron DeSantis
and Trump felt compelled to leave that message,
even though I hadn't endorsed him.
It was very thoughtful message.
So I sit down, I'm in a hotel in Orlando,
and I woke up and I went and I listened to that message.
And I thought, all right, I'm gonna talk to his staff
about going to Wisconsin and doing this endorsement.
So I dialed the number and on the second ring,
I hear, hello, this is Donald.
And I was like, oh shit, that's his cell number.
And he's like two weeks from prison or president.
Nobody knows any, and he's taken my call.
- That's America.
- And I was taken off guard.
'Cause I thought it was, I was like, oh crap.
- Now what do you do?
What do you fricking do, Thomas?
- I'm sitting here in my boxers in a Marriott.
- Oh God, at least go outside and stand up.
You weren't sitting down, were you?
- No.
- 'Cause your audio, your volume's better
if you walk around where you're talking to somebody.
- So the first thing I did was to thank him
for leaving the message.
- Oh, that's good.
About my wife 'cause I hadn't done that yet.
And he said, that's a hard one.
That's a very hard one.
You know, Arnold Palmer, he played around a lot,
but he did love his wife.
And when she passed away, it almost killed Arnie.
I mean, it was tough on Arnie, but he's a tough cookie.
You're a tough cookie too.
And, you know, you're like Arnie, you'll get through this.
And then he goes, I take it back.
You're much tougher than Arnie ever was.
So then he goes, you're sharp cookie too.
You know, you went to MIT.
My uncle, Professor John G. Trump,
taught at MIT for 41 years.
It's a record.
Then he said--
- Oh, what a God.
- Then he goes, I've got the best genetics.
And then I'm like, I'm thinking, wait,
this guy is two weeks away and he's gotta be busy, right?
This is the election of his life.
And so I thought, you know, at some point,
they're gonna grab him and say, look,
who are you talking to?
You gotta get back to work.
- Yeah.
- So I said, well, the reason I'm calling you is I wanna,
I've seen it's close in these purple states
and a lot of independents and libertarians
who could be influenced perhaps.
And I'd like to endorse you.
Oh, this is wonderful, this is great, this is tremendous.
And I said, well, how do we get it out there?
And he goes, oh, just tweet it, I'll retweet you.
So I saved myself a trip to Wisconsin.
- Oh, that's nice, dude.
I love going to Wisconsin.
Was it in La Crosse?
- I don't know where it was.
- Ugh, you missed out, I think.
- So he goes, you know,
I spoke at the Libertarian National Convention.
- Yeah, there it is, there's, oh, yeah.
There's a sentence in here I gotta explain.
Okay, so he goes, I spoke at the Libertarian Convention
and they loved me.
He said, when I mentioned I was gonna free that kid
that's been locked up 100 years, they all applauded.
- Who was that, not Travis Scott or something?
- Ross Ulbrich.
So I said, oh yeah, he's in for two life sentences,
plus 40 years for running a website.
And he said, yeah, put that in your endorsement.
The Libertarians will love it.
- Oh, really?
So he really thought of that?
- So if you look, like, I'm just like,
he will make America healthy,
he'll save America, secure our liberties.
I said, and he'll free Ross Ulbrich.
- Wow, so a lot of people are like, we'll take it.
- Yeah, Ross's mom called me and thanked me for that.
And then--
- Is he out?
- Yeah, I took him to the State of the Union.
- Is he a cool guy?
- He's a super cool guy.
- And he never should have been in prison
for as long as he was.
- Yeah, what did he get locked up for?
- Running a dark web website called Silk Road
that allowed people to buy and sell things on the internet.
- Oh yeah, and they started selling dope and shit on there,
and people were dying.
- Yeah, so that's what--
- He's holding for a year.
- But I mean, that's the thing.
- But it's like, you can't lock him up,
you can't lock him up and not lock up.
- All the perpetrators on the website are free, right?
- No, I'm talking about you can't lock him up
and not lock up the Sackler family, though.
- You keep going back to that.
I don't know what you're talking about.
- Oh, they're the family that did the opioid epidemic
or whatever.
- Oh, okay.
- They're the Purdue Pharma family.
- Oh, okay, okay.
- So anyway, yeah, I'm sorry.
They're just like mass murders or whatever.
I mean, they're allegedly mass murderers
that are still wandering around.
So anyways, the thing is, so I said, all right,
I'll put that sentence in.
Let me, I want to run this by you.
And he said, here, I'll give you to Dan Scavino.
He's on the plane with me.
And I'm like, oh my gosh, he's on a plane?
He's talking to me.
He said, we're going to go tape the Joe Rogan show.
- Oh, really?
- Then he like, I can hear him hand the phone.
- Oh, that was right before the election, dude.
- Yeah, he hands the phone to Scavino.
And he's like, I don't think he knew I could hear him,
but he goes, Dan, this is a tough cookie.
It's Thomas Massey.
Don't screw this up.
- Oh.
- Then we worked out the endorsement.
- That's pretty cool, huh?
- It was cool.
'Cause then instead of like a bunch of staff
trying to figure out what to do, I just called him.
And we got it done in like five minutes, right?
But, and I did endorse him.
And then I'm obviously I'm not the ag secretary,
but that's okay.
I'm happy where I'm at.
I would have done it if he needed somebody to do it.
- But are you guys at odds, do you feel like?
Or do you feel like there's so much going on in his world?
- Well, he came over to Congress a few weeks ago.
- Okay.
- To whip us on the Big Beautiful Bill.
- And so when that happens,
you guys all get together in a room and he gets to speak?
- Yeah, 200 people in the room.
- Okay, and so he's petitioning
for the Big Beautiful Bill.
- Yeah, he's telling us how great it is.
And then he says something about me.
And then he realizes I might be in the room.
He said, "Is Tom Massey in the room?"
And I raised my hand and he looked at him.
He said, "You know, the thing about Tom Massey is
he's very much like Rand Paul.
They're both from Kentucky.
You can never get him to vote for anything."
And they got the same hair.
- That's pretty true, huh?
- Then he goes, "Actually, I like Massey's hair better."
So all my colleagues, they were approving of me that day.
- That's hilarious.
- Yeah, there's, I mean, some people hate Donald Trump.
Some people love Donald Trump.
I just think you cannot deny that he is nobody like him.
- There's two forms of Trump derangement syndrome, though.
There's the kind where you hate him so much,
it's irrational.
And even if he's for something you support,
you'll still be against him.
And a lot of liberals have Trump derangement syndrome,
and some Republicans.
- Well, that's a general thing.
And I think that's just a political derangement syndrome, too.
I mean, I have friends, it's like,
you could show them the same exact thing,
but if it's a Republican saying it or a Democrat,
and they'll choose the other side, you know?
- Well, that's why there's the other version
of Trump derangement syndrome,
which is you love him so much
that when he goes against something he said he would do,
or he does something that's against your principles,
you change your own principles to support him.
And I think that's just as dangerous.
- And I try not to have either of the Trump derangements
syndrome, so, you know.

Thomas Massie on His Testy Relationship with Donald Trump

- Do you think that Trump wants a war in Iran?
- No, I don't.
I actually don't.
And I've talked to him on the phone about this.
When, do you remember there was a general from Iran
called Soleimani who was basically taken out
while he was in Iraq during the first Trump presidency.
- Bring up Soleimani.
- Yeah, there you go.
- Ooh, interesting looking guy.
He almost looks like two different people
put into one head.
- So they took him out when Trump was president.
- Is he a good guy or a bad guy?
- Bad guy.
- Okay.
- Okay, and then, and I'm not here to litigate that,
but Trump was talking about attacking Iran after that.
I think they shot down one of our drones,
and so tensions were escalating,
and the Democrats put a bill on the floor
to say that you can't go,
basically like my bill this time,
says you can't go to war without a vote of Congress.
And I vote, I was one of three Republicans
who voted for that resolution,
but Trump found out I was gonna vote for it,
and he called me up,
and tried to talk me out of voting for it.
- Mm-hmm.
- And in that conversation,
we talked about war with Iran,
and he genuinely, I do believe,
he genuinely didn't want war with Iran.
His argument to me was that if we,
if Congress gave him the authority to threaten them,
that he could keep us out of a war with the threat.
- Oh, I see.
So that's a strategy.
- It is a strategy.
The problem with the strategy, I told him,
was, okay, if I vote to give you that authority
to declare war, or on your own,
- Mm-hmm.
- you know, preemptively...
- How do I know it will happen?
- Well, what if they call your bluff?
- Mm-hmm.
- And then, now we're in a war,
and I don't get a chance to vote on it,
because I just said, we don't need to vote on it.
And he was not happy with that reasoning, but...
- Well, 'cause I guess, I guess his thought would be,
well, if I tell you I'm not gonna do it no matter what,
then why wouldn't you support me, probably?
- Yeah.
But you can't know that he won't.
And by the way, he told me, he said,
"I'm more libertarian than you are."
- Oh, yeah, really?
- Oh, man, Donald Trump is an interesting guy, man.
What an anomaly of a human being, I think, right?
- He is.
There'll never be another person like him,
particularly not one that becomes president.
And I've been on his good side,
and I've been on his bad side,
and it seems like every couple years, it flips.
- Yeah, I saw, didn't you get uninvited
to the picnic or something?
Was that a thing that, was that a real thing that happened?
- That was a real thing that happened.
- A meme about it or something that you got uninvited to the...
At the last minute, I got re-invited.
But this goes back to 2020, during COVID.
I was the only one who said we're, you know,
this CARES Act is going to bankrupt the country.
Basically, it's going to cause massive inflation and shortages.
So I opposed that.
And the president called me, he was upset with me,
that I would force Congress to return during COVID and vote.
And basically, all I said was, look, this was during COVID.
They wanted to spend $2 trillion by unanimous consent.
I said, if truckers have to work and farmers have to work
and nurses have to work,
why doesn't Congress show up and vote on this?
- Yeah.
- So at the time, he called me a third-rate grandstander
and said I should be thrown out of Congress.
The media immediately descended on me and said,
what did I have to say for myself?
Because he was tweeting all of this.
And they said, well, I'm at least second-rate.
Come on.
- Yeah, help me out here.
- Two years later, he endorsed me for a re-election.
And then, most recently, Bobby Kennedy joined a coalition
with the president for Maha, Make America Healthy Again.
And you can do that through the National Institute of Health
and FDA and CDC and all that.
But also, our food supply is a big, important part of that.
So Bobby Kennedy was advocating for me
to be the Secretary of Agriculture.
And he and I have been talking about it for weeks.
This was before Trump won the election last fall.
- And there's a lot of agriculture out of Kentucky.
That would have been great.
- It would have been great.
- Would it have been something you were interested in?
- Yes, definitely.
'Cause I think there are a lot of things we could do
to basically reinvigorate and empower small farmers
to make healthy food and grow local economies,
things like that.
And so I was all in.
And Bobby Kennedy's team spent a lot of time on it.
And I told him, this was like in October
before the election, I said,
I think there's one problem with your plan.
And he said, what's that?
And I said, I've not endorsed Trump.
And he said, well, it sounds like you need to endorse Trump.
- Do you think that was a strategy
or do you think that it was--
- No, he was genuine.
- Yeah, I would think so.
- And I agreed with him.
So I said, well, how do we announce it?
And he said, we'll come out to Wisconsin Tuesday.
And Tulsi and I are doing this rally
and just come up on stage and announce it there.
And I'm thinking, man, I don't wanna go to Wisconsin
in October to do this.
'Cause I had a lot of other things on my plate at that time.
And so I put it off for a day.
I did look at plane tickets to go to Wisconsin.
I typed out an endorsement of Trump on my iPhone,
read it back to myself.
And I woke up the next morning,
and I thought, this is the day, I gotta do this.
So Trump, when my wife passed away last summer,
he had left a very nice message.
I would have obviously taken his call,
but I was inundated with calls,
but he left a really nice message of condolences.
- That was thoughtful of him.
- And so it was, and that's a side people don't see, right?
I actually campaigned for Ron DeSantis
and Trump felt compelled to leave that message,
even though I hadn't endorsed him.
It was very thoughtful message.
So I sit down, I'm in a hotel in Orlando,
and I woke up and I went and I listened to that message.
And I thought, all right, I'm gonna talk to his staff
about going to Wisconsin and doing this endorsement.
So I dialed the number and on the second ring,
I hear, hello, this is Donald.
And I was like, oh shit, that's his cell number.
And he's like two weeks from prison or president.
Nobody knows any, and he's taken my call.
- That's America.
- And I was taken off guard.
'Cause I thought it was, I was like, oh crap.
- Now what do you do?
What do you fricking do, Thomas?
- I'm sitting here in my boxers in a Marriott.
- Oh God, at least go outside and stand up.
You weren't sitting down, were you?
- No.
- 'Cause your audio, your volume's better
if you walk around where you're talking to somebody.
- So the first thing I did was to thank him
for leaving the message.
- Oh, that's good.
About my wife 'cause I hadn't done that yet.
And he said, that's a hard one.
That's a very hard one.
You know, Arnold Palmer, he played around a lot,
but he did love his wife.
And when she passed away, it almost killed Arnie.
I mean, it was tough on Arnie, but he's a tough cookie.
You're a tough cookie too.
And, you know, you're like Arnie, you'll get through this.
And then he goes, I take it back.
You're much tougher than Arnie ever was.
So then he goes, you're sharp cookie too.
You know, you went to MIT.
My uncle, Professor John G. Trump,
taught at MIT for 41 years.
It's a record.
Then he said--
- Oh, what a God.
- Then he goes, I've got the best genetics.
And then I'm like, I'm thinking, wait,
this guy is two weeks away and he's gotta be busy, right?
This is the election of his life.
And so I thought, you know, at some point,
they're gonna grab him and say, look,
who are you talking to?
You gotta get back to work.
- Yeah.
- So I said, well, the reason I'm calling you is I wanna,
I've seen it's close in these purple states
and a lot of independents and libertarians
who could be influenced perhaps.
And I'd like to endorse you.
Oh, this is wonderful, this is great, this is tremendous.
And I said, well, how do we get it out there?
And he goes, oh, just tweet it, I'll retweet you.
So I saved myself a trip to Wisconsin.
- Oh, that's nice, dude.
I love going to Wisconsin.
Was it in La Crosse?
- I don't know where it was.
- Ugh, you missed out, I think.
- So he goes, you know,
I spoke at the Libertarian National Convention.
- Yeah, there it is, there's, oh, yeah.
There's a sentence in here I gotta explain.
Okay, so he goes, I spoke at the Libertarian Convention
and they loved me.
He said, when I mentioned I was gonna free that kid
that's been locked up 100 years, they all applauded.
- Who was that, not Travis Scott or something?
- Ross Ulbrich.
So I said, oh yeah, he's in for two life sentences,
plus 40 years for running a website.
And he said, yeah, put that in your endorsement.
The Libertarians will love it.
- Oh, really?
So he really thought of that?
- So if you look, like, I'm just like,
he will make America healthy,
he'll save America, secure our liberties.
I said, and he'll free Ross Ulbrich.
- Wow, so a lot of people are like, we'll take it.
- Yeah, Ross's mom called me and thanked me for that.
And then--
- Is he out?
- Yeah, I took him to the State of the Union.
- Is he a cool guy?
- He's a super cool guy.
- And he never should have been in prison
for as long as he was.
- Yeah, what did he get locked up for?
- Running a dark web website called Silk Road
that allowed people to buy and sell things on the internet.
- Oh yeah, and they started selling dope and shit on there,
and people were dying.
- Yeah, so that's what--
- He's holding for a year.
- But I mean, that's the thing.
- But it's like, you can't lock him up,
you can't lock him up and not lock up.
- All the perpetrators on the website are free, right?
- No, I'm talking about you can't lock him up
and not lock up the Sackler family, though.
- You keep going back to that.
I don't know what you're talking about.
- Oh, they're the family that did the opioid epidemic
or whatever.
- Oh, okay.
- They're the Purdue Pharma family.
- Oh, okay, okay.
- So anyway, yeah, I'm sorry.
They're just like mass murders or whatever.
I mean, they're allegedly mass murderers
that are still wandering around.
So anyways, the thing is, so I said, all right,
I'll put that sentence in.
Let me, I want to run this by you.
And he said, here, I'll give you to Dan Scavino.
He's on the plane with me.
And I'm like, oh my gosh, he's on a plane?
He's talking to me.
He said, we're going to go tape the Joe Rogan show.
- Oh, really?
- Then he like, I can hear him hand the phone.
- Oh, that was right before the election, dude.
- Yeah, he hands the phone to Scavino.
And he's like, I don't think he knew I could hear him,
but he goes, Dan, this is a tough cookie.
It's Thomas Massey.
Don't screw this up.
- Oh.
- Then we worked out the endorsement.
- That's pretty cool, huh?
- It was cool.
'Cause then instead of like a bunch of staff
trying to figure out what to do, I just called him.
And we got it done in like five minutes, right?
But, and I did endorse him.
And then I'm obviously I'm not the ag secretary,
but that's okay.
I'm happy where I'm at.
I would have done it if he needed somebody to do it.
- But are you guys at odds, do you feel like?
Or do you feel like there's so much going on in his world?
- Well, he came over to Congress a few weeks ago.
- Okay.
- To whip us on the Big Beautiful Bill.
- And so when that happens,
you guys all get together in a room and he gets to speak?
- Yeah, 200 people in the room.
- Okay, and so he's petitioning
for the Big Beautiful Bill.
- Yeah, he's telling us how great it is.
And then he says something about me.
And then he realizes I might be in the room.
He said, "Is Tom Massey in the room?"
And I raised my hand and he looked at him.
He said, "You know, the thing about Tom Massey is
he's very much like Rand Paul.
They're both from Kentucky.
You can never get him to vote for anything."
And they got the same hair.
- That's pretty true, huh?
- Then he goes, "Actually, I like Massey's hair better."
So all my colleagues, they were