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October 22, 2025 27 mins

A lone biplane drops homemade bombs over Havana as the 1933 revolution upends Cuba—and the Arnaz family. Desi’s father is jailed, stripped of wealth, and exiled, forcing teenage Desi to start over in Miami with no English, no money, and no roadmap. Wilmer Valderrama traces Desi’s survival sprint: faking English at dinner, getting pummeled in a surprise “yes-okay” boxing exhibition at Saint Leo’s, and cleaning canary cages for $15 a week—where a lesson in American salesmanship (package the experience, not just the product) sparks the mindset that will one day power Desilu. It’s the raw prelude to showbiz: resilience, reinvention, and the immigrant grind.

Featuring: Wilmer Valderrama (That ’70s Show, NCIS, Encanto)
Topics: Desi Arnaz, 1933 Cuban Revolution, Gerardo Machado, Fulgencio Batista, exile to Miami, Saint Leo College Prep, immigrant English learning, boxing exhibition, canary cage business, American salesmanship, Desilu origins, Hollywood history, Latinx representation.

Starring: Desi Arnaz and Wilmer Valderrama is produced by WV Sound in partnership with iHeart’s My Cultura Podcast Network.
Starring: Desi Arnaz and Wilmer Valderrama is written by Erick Galindo and narrated by Wilmer Valderrama. It is produced by Sophie Spencer-Zavos and Leo Klemm, with special help from Angel Lopez Galindo.

Executive producers are Wilmer Valderrama and Erick Galindo.

This episode was edited and engineered by Sean Tracy and features original music by Halo Boy and Madison Davenport. Cover art illustration by Lindsey Mound. Voice acting by Eddie Mujica, Luke Barr, and Ally Maldonado

For more podcasts from iHeart, visit the iHeartRadio app or wherever you listen to your favorite shows.

See omnystudio.com/listener for privacy information.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:22):
There's a small plane flying over Habana and he's dropping bombs.
The Cuban revolution of nineteen thirty three that had taken
everything the Arnest family built was still in his early
stages Wadsi would later refer to as anarchist, and Bolsheviks

(00:48):
had taken over the presidential Palace, and here's this guy
in an old school World War One airplane trying to
fight back by dropping homemade bombs on the palace. But
he's got a terrible aim, so instead of hitting the palace,
he keeps hitting businesses, homes, cars, people. Whatever had been

(01:12):
left standing by the revolutionaries is now being threatened by
this long wannabe war plane, and the civilian casualties are mounting.
Here's an excerpt from Desi's memoir.

Speaker 2 (01:29):
My aunt lived three blocks from the palace, perhaps the
last place he wanted.

Speaker 3 (01:33):
To be besides the palace itself, because these.

Speaker 2 (01:35):
Asshole dropping bombs never came close to hitting the palace. Oh,
he hit everything around it instead. At an outdoor cafe,
a kid playing the Moroccas he lost his arm. A
couple on the beach, which was also about three blocks
from the palace, they were killed too.

Speaker 3 (01:53):
People coming out of the theater four blocks away were hit.
He was intense.

Speaker 1 (02:07):
Desi recalls this moment with a touch of cynical humor.
I get it. I mean it's a Latino thing, right,
or maybe it's an immigrant thing. When bad things keep happening,
you learn to have a little sense of humor about it,
or else you just wind up sad or angry. But
that doesn't take away how traumatic this moment was for Dessi.

(02:28):
Imagine being a teenager and having to experience all this violence.
It left a deep impression on Dessi.

Speaker 2 (02:38):
There was this one site I will never forget. A
man's head stuck on a long pole and hung in
front of his house. The rest of the body was
hung two doors down in front of his father's house.

Speaker 1 (02:53):
Well, all of this was going down in Havana. Dessi
and his mom are hiding out at their uncle's house.
A lawyer was a member of the political opposition party
to the outstead President Machado, so they were safe there.
But Dessi's dad, this Adio, was in Machallo's inner circle.

Speaker 4 (03:14):
In Nevana. President Machado was forced to flee to Miami
this morning along with high ranking members of his party.
It was a chaotic scene with a hasty departure at
a time when communism is on the rise. Crowds gathered
in the streets cheering the end of the administration, while
reports of looting and violence and key government buildings continued
to trickle in. With no clear leadership in place, the
nation faces an uncertain future, even as many Cubans rejoice

(03:38):
in Machado's Hall.

Speaker 1 (03:41):
Thus recreated from the news reports around that time. But
I like the way Dessi puts it in his memoir.

Speaker 2 (03:48):
A book Manchallo left in the early morning with five
guys in pajamas.

Speaker 1 (03:54):
The crazy part is that this Adio, this his father,
could have been one of those guys in pajamas.

Speaker 2 (03:59):
That had actually gone to the airport with the president,
and he could have left for Miami with him on
his private plane. My chather in fact, urged my father
to flee, but Dad thanked him and told the President
not to worry. Nothing was going to happen to a
little fish like him.

Speaker 1 (04:17):
Decided was wrong. Things were happening. Members of Mitchell's government,
ranging from local officials to high ranking senators, were being
rounded up and thrown in jail or worse, According to Desi,
his dad should have known better.

Speaker 2 (04:32):
Santiago l Coula had been the first town in the
island in which a communist had been thrown in jail
during my father's second term as mayor. That probably explains
why they couldn't wait to destroy everything he had the
minute they were able to do so.

Speaker 1 (04:52):
You're listening to starry in Dessier Nacon Wilmer Valderama, the
real life story of the Latin immigrant who basically invented
the modern Hollywood system. But first he had to watch
his father, once one of the most powerful men in Cuba,
lose everything, his home, his wealth, his country, and then
together come to America to start over from nothing. That's

(05:15):
after the break. When I was about eleven or twelve

(05:44):
years old, I started to notice that my dad was
selling things that we owned. His everyday wardrobe, which had
been very business like, became more casual. He wasn't buying
new shirts anymore. I'll never forget the day that sold
his Burgundy fifth will Continental. He was so proud because
he had installed this tiny, little, very tiny, little black

(06:05):
and white television and ended up buying a moped in
its place. Then one Christmas, my dad had to break
the news to us that, well, there will be no
gifts this year. He said, in his gravelly voice, your
mother and I yeah, I need you to understand and

(06:28):
have a patience. We were sad, but we understood right.
It's you know, you put all your trust in our
parents and now you're doing it together. My dad had
his reasons, but what was hard to understand was the

(06:49):
turmoil in Venezuela's politics in the early nineteen nineties. There
was rampid corruption, a system where politicians stopped talking to
each other and used to collaborate. Poverty, inflation, looting, riots.
People were becoming desperate, and as well, I was falling apart.

(07:20):
The unrest led to an opening for a military officer
named Ugo Chavis, who tried to seize control of the
government by force. He failed and was thrown into prison,
but he had his supporters. People rided and protested outside
the prison. The people who knew best saw this strong,
frenzied support of Chavis and suspected the worst. Chavis wasn't

(07:45):
the answer to our country's problems, but it was clear
Chavis with me back. My dad decided it was time
for a change. We sold everything, even my beloved horse Ornado. Again,
my dad set us down and told us we were
moving to the United States. We leave this Thursday. He said,

(08:07):
you'll need to learn in the English, and I said
that you too. Well. Unlike Jess, our family didn't have

(08:27):
to flee the revolution and a dictator. We were lucky
we left before things got really bad in Venezuela. But
I know what it feels like to lose your old
life and start over, to be an outsider in a
new country where you don't know the language or get
the culture. And for the ar Nest family, the journey

(08:54):
was a lot more dangerous. After hearing about the destruction
of his family's home and seeing what was going on
in the nation's capital, Decidi decided he wasn't going to
wait to see what the new regime had in store

(09:14):
for him.

Speaker 2 (09:16):
Dad decided to turn himself in at La Cavanya, where
they had promised him protection until law and order could
be restored.

Speaker 1 (09:26):
When Dessey and his mom Lola found out that Saudio
was imprisoned in Havana, where bombs were falling from the sky,
they decided to rush to him to avoid the angry mobs.
They decked out the car and revolutionary propaganda and shouted
Viva Lavulacion along the way Costplaine. As revolutionaries paid off,

(09:49):
they made it to Havana and Dessi finally got to
have a heart to heart with his father about all
the unrest and turmoil the last forty eight hours.

Speaker 2 (09:58):
I asked him, how can some like this happened overnight?
You know, it didn't happen overnight, he told me. When
so many people are hungry and don't have a decent
place to live, you know, medical care and good schools
for their children, clean towns, without the flies or mosquitoes,
without the continuous thread of typhoid, yellow fever, and all

(10:19):
the other maladies synonymous with dirt, they're apt to revolt.
There was a lot of unrest, but nobody expected it
would wind up like this, you know, except the ones
who were waiting to use it.

Speaker 1 (10:49):
Cuba had experienced several uprising and revolutions even before nineteen
thirty three. In fact, you could argue Cuba as a
modern nation has been in constin revolution, just like the
United States and many Latin American countries. Cuba was born
after revolutionaries declared their independence from the European conquistadors. He

(11:11):
was independence fight with Spain climax in the Spanish American
War of eighteen ninety eight. Yeah, even back then, the
United States had a lot of interest in what happened
in this little Caribbean island, but Cuba had never really
been independent. The US often interfered in Cuba's internal politics,

(11:34):
which remained marked with periods of military rule, dictatorship, and corruption.
According to Desi's dad, nineteen thirty three's overthrowed of Machado
was no different.

Speaker 2 (11:47):
That said, I have to believe that not even some
nor Welles, the American ambassador to Cuba at the time,
realized what he was doing when he forced Machado sot
in flight. Everybody wanted to get rid of Machado. Even
I was getting disenchanted with the man. And if mister
Wells had not acted so stupidly, everything would have been
all right. He overlooked the fact that a country suddenly

(12:10):
left without an a chief of state would not have
time to replace him in an orderly and lawful manner.
That compared it to what would happen if the main
supporting wall of a building was rotten and had to
be cut down and replaced before you cut it down.
He said, You've got to make sure all the other
walls in that building are well assured and secured, because

(12:30):
if they are not, and you just cut the rotting
one down and throw it away, well the whole building
will collapse.

Speaker 3 (12:37):
And that, unfortunately, is what happened to Kula.

Speaker 1 (12:43):
For the next six months, the revolution rage as the
factions with him a Chattle's opposition thought to fill the
power vacuum with a guy named full Henzio Baptista, eventually
maneuver in his way to the top. If that name
sounds familiar, it's probably because as Bautista as the guy
fied al Castro eventually overthrew in nineteen fifty nine. Like

(13:05):
I said, Cuba at times feels like it's in a
constant revolution, But in many ways, the revolution of nineteen
thirty three marked the beginning of the end for democracy
in the little island paradise. For Dessi and his family,
the revolution not only shattered their privileged life but also
permanently altered their homeland. Cuba had been forever changed, and

(13:28):
so had Dessi's future. After six months in prison, Dessi's dad,
the former mayor of Santiago, a siting congressman from one
of the richest and most affluent families in Cuba, was
released from prism on two conditions. First, he would see
all of his power, money and property, and second he

(13:49):
would be exiled, forced to flee the country and start
over with nothing. Thankfully, for the Satio, he was a
short board right to Miami. There's his family settled in Miami,

(14:09):
not the Miami we know now where Cuban culture dominates
so much that it's changing the language.

Speaker 5 (14:18):
Have you ever noticed how people from Miami have a
very specific way of speaking English. That's called Miami English,
and it's a full on dialect here in Miami. It
makes a standard American English and Spanish rhythm and pronunciation
thanks to generations of Cuban, Caribbean and Latin American influence.
It takes Spanish words and phrasing and directly translates them
to English, but keeps a Spanish structure. For example, you'd

(14:38):
make a party instead of having a party or throw
a party, because that's how it's set in Spanish. These
phrases are being used by everyone filingual Spanish and English speakers.

Speaker 1 (14:49):
In nineteen thirty three, when sixteen year old Desi er
Naz first arrived. Miami was a much different place. Language
was a huge barrier. Here's how Desi called it in
his memoir.

Speaker 2 (15:04):
Well, I walked around and found what looked like a
modest restaurant, but you know, nice and clean. A real
cute waitress brought me a menu. I looked up and
said thank you, and opened it. After looking it over,
I began cursing the Jesuits.

Speaker 1 (15:20):
The Jesuits were the professors at Dessie's private Catholic schools
back in Cuba.

Speaker 2 (15:25):
Not only had they failed to teach me how to
understand or speak English, they had not even taught me
how to read it.

Speaker 1 (15:32):
Remember, Dessi studied hard to raise his final exams and
passed junior year of high school. Up until that point,
he had taken several years of English, starting from a
very younger age. But there is the kind of English
you learn in a textbook and the kind you need
to order breakfast.

Speaker 2 (15:51):
Well, that waitress was standing by my side with a
pat and a pencil.

Speaker 3 (15:55):
I looked at her and smiled again. She looked at
me and smiled back.

Speaker 2 (16:00):
You know, she said something that sounded like, are you
about to order your dinner right now. That's the trouble
with a foreign language, you see, nobody stops being between
the words. She could have said, are you going to
sit there all the fucking night? Or are you going
to order your dinner? You silly looking Cuban, and I
wouldn't have known the different.

Speaker 1 (16:22):
So there's Dassi, sixteen, starving looking at the menu in
the language he doesn't understand, no photos, trying to order
some dinner.

Speaker 2 (16:32):
I pointed to four different lines in the menu. I
wound up with four different kinds of soup, which I
ate or drank or whatever the hell you call it,
as if this were what I normally order for dinner.
I thought she looked kind of funny when I pointed
to the four different lines on the menu. And by
the time she brought me the second plate of soup,
well I knew why.

Speaker 1 (16:56):
I feel you, Dessie. I still remember my first time
trying to speaking well, let's just say I had no English.
I'm at an American gas station. They didn't know how
to ask for the bathroom key, so I just stood
there silently staring at the attendant until they figured it
out and handed it over. If you grew up speaking English.

(17:17):
You might not realize how hard it is. I started
it all through school in Venezuela. But learning it in
a classroom is one thing. Hearing it in real life
is like trying to sob a puzzle where the pieces
keep changing shape and the rules have too many exceptions.

Speaker 6 (17:36):
I don't have to leave the country after graduation, that's
in that week, and I have to relearn my native language.

Speaker 1 (17:48):
Good day.

Speaker 3 (17:48):
No first.

Speaker 1 (17:52):
Look, I can laugh about it now, but it's hard
to learn the language when you're overwhelmed trying to keep
your family afloat and just trying to survive. People will
speak English when you're in America. This he got a
lot of this too, and it was a struggle for years.
Oftentimes he had to fake it English.

Speaker 3 (18:14):
Oh no, it sounds really worse than that. Double talk.

Speaker 2 (18:16):
And the thing with the English is very annoying to
listen to, especially when someone's trying to talk to you
and just talking, talking, talking, So if I don't want
to hear what they're saying, you know, I just look
at them and smile and pretend like I understand and
say ah, yeah, okay, okay.

Speaker 1 (18:33):
Look I get this is frustration learning English is easier
said than done. I don't know how many times early
on as a kid, when I was struggling to learn
the language, that I had to pretend I understood what
someone was saying. In fact, I didn't learn English until
well into high school, and that was from a combination

(18:53):
of class, TV, music, and hanging around other English speaking kids.
But that's the privilege my parents and gave me right
a chance to focus on betting on myself in a
nice high school, and that's exactly what Desi needed at
that time. But after a horrible few months, was not
even in the cars for him. His family was broken
and beaten. I mean, it was definitely time for the

(19:17):
Arnest family to get a little bit of good news.
And that is after the break. After the hellish escape

(19:39):
from Cuba, Desi's dad didn't have any money, having lost
the family fortune to the revolutionaries. He had to really
think hard about how he was going to give Desi
a shot at making it in a new country, and
education was the only thing he could really think of. Now,
Desaudio didn't have his political cloud or his fortune anymore,

(20:01):
but he still had some connections.

Speaker 2 (20:04):
Machado owed my dad for helping him get on that
plane escape in Cuba. The anarchists could have done their
worst with Machado, and there was plenty of room on
the plane for that.

Speaker 3 (20:14):
Though I guess maybe it would have been too heavy.

Speaker 2 (20:17):
You see, Machado had several socks of gold with him
on that plane.

Speaker 1 (20:22):
Machado and his sacks of gold were doing alright in Miami,
thanks in part to this ideos helping him escape. So
this audio decided to cash in a favor of Machado.

Speaker 2 (20:32):
Oldham Dad asked his former president to help me get
one of those, you know, a great American education, So
Machado agreed to pull some strings.

Speaker 1 (20:47):
Dessi would finish his high school career at Saint Leo
College Preparatory School, about thirty five miles north of Tampa Bay.
He was a prestigious Catholic military boarding school run by
Benedictine monks, known for its strict discipline and a traditional
Catholic education with a strong emphasis on character development, faith,

(21:09):
and academic rigor alongside military style structure and training. In
his memoir des he recounts his time there as both
challenging and formative, shaping his resilience and adaptability as he
adjusted to life in the United States. But my favorite
story of his as Saint Leo's is about boxing.

Speaker 2 (21:33):
So about three weeks after I arrived at Saint Leo's,
one of the brothers, who was in charge of athletics,
came to me with one of those you know what,
I said, A long explanation, and I don't understand.

Speaker 3 (21:43):
I'm just looking at him like, yeah, yeah, okay.

Speaker 1 (21:47):
Desi was still struggling to understand English, so he had
no idea where he had just agreed to.

Speaker 2 (21:53):
So the next evening I went to the boxing class
and I noticed, all of a sudden, there's this packed
house was in the ring making some kind of announcement.
Everyone was applauding and looking at me. I'm looking at them.
I knew something was screwy, but I couldn't figure out what.

Speaker 1 (22:15):
The priest called Dessi into the ring and helped him
with his boxing gloves. On the other side of the
ring was Deasi's boxing coach. Dessi thought it was weirder
to have this big of an audience for a boxing lesson,
but he went with it anyway. Then the bell rings
and he goes towards the coach.

Speaker 2 (22:40):
The first time he hit me. I knew, damn well,
it was not a lesson. Okay, I landed right on
my ass. While on it, I was thinking, how the
hell did I get into this?

Speaker 3 (22:51):
You know?

Speaker 2 (22:52):
I got up and started to dance a little. Keep moving,
keep moving, I was telling myself. When I thought I
saw an opening, I threw it right and got hit
with three combinations. Down on my ass again. Well they
went like that for about three whole rounds. I never
got such a beating a day in my life. What

(23:13):
that happened was when I said yeah, yeah, okay to
the brother, I okayed an exhibition match.

Speaker 1 (23:24):
See what I mean now, I knowing English can be dangerous. Thankfully,
he taught Dessi to stop saying yes to things he
didn't understand. Learning English became a top priority. So I
was getting a job. With his mom still behind in Cuba,
Dessi and his dad struggled to find a place to live,

(23:46):
eventually settling in a warehouse that doubled as the family business.
They did odd jobs, important plantains and selling tiles, and
Dessi even worked as kind of a pet janitor for
a man named mister Whitehouse.

Speaker 2 (24:02):
This mister white House he had a hobby canary breeding. Yeah,
he had so many canaries that he had converted his
garage into.

Speaker 3 (24:10):
One big cage.

Speaker 2 (24:12):
One day when I was visiting them, he told me
he had figured out a way to make money with
these canaries. He was going to buy one hundred cages,
put a canary in each cage, and then place them
on consignment in drug stores around Miami, Miami Beach, and
Coral Gables, with a different price on each canary and
its cage.

Speaker 1 (24:32):
But the cages needed to look good and will birds
they let's just say the poopy kanaka a lot. So
this is he got a job cleaning the cages.

Speaker 2 (24:43):
I would start every day in Coral Gables, then go
to Miami and finish in Miami Beach. That last goddamn
canary I took care of each day was the one
closer to Saint Patrick's. And that's where I had a
little problem. You see, I didn't want the kids from
school to catch me at my job, so I spent
a lot of time hiding behind piles of Contex and

(25:04):
Kleenex boxes. Oh yeah, I got fifteen dollars per week
and my supper and mister Whitehouse he sold all his canaries.
It was a really good business, providing you had a
garage full of canaries.

Speaker 1 (25:25):
This he learned something valuable about the canary cages. The
owner of the business really dressed them up and made
a show out of the bird cages.

Speaker 2 (25:34):
If one cage was fancier and had a better canary
than others, Wow, it would sell for twenty five ninety five.
Others would sell for fifteen ninety eight or twelve ninety nine,
but never for twenty six, sixteen, or thirteen. This was
a good lesson in American salesmanship. People would come into
the store, see the pretty cage, hear the canaries singing

(25:56):
and chirping, read the book of instructions hanging on each
cage how to take care of them, and the months
supply of special canary food.

Speaker 3 (26:04):
This all made an attractive back of the deal.

Speaker 1 (26:07):
Seeing how mister Whitehouse package and sold the experience of
the canaries, not just the canaries themselves, really opened Desi's
eyes to the possibilities of making money in America. You
didn't have to be a lawyer like his uncles or
a politician like his dad to make it. This inspired
Dessi to do something his father would never approve of

(26:28):
chase a job and music, and that is on the
next episode of Starry, starring Desi Rnass and Wilmer val
Durama is produced by WV Sound in partnership with Iheartmichael

(26:49):
Duda podcast Network, starring Desi Rnass and wilmerval Durama is
written by Eric Galindo and narrated by me Wilmer Valdorama.
It is produced by Sophie's Shavos and Leo Klem, with
special help from Anhel Lopez Galindo. Our executive producers are
myself and Eric Galindo. This episode was edited and engineered

(27:11):
by Sean Tracy and features original music by Halo Boy
and Madison Devenport. Our cover illustration is by Lindsey Mount.
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