Okay, I want everyone to just take a second,
look at the calendar. It's Monday, February 16th,
2026. And I feel like the entire world needs
to take a collective deep breath. A very, very
deep breath. It has been an absolute whirlwind.
Whirlwind is, I think, putting it mildly. Yeah,
that might be an understatement. We are sitting...
Right now in the immediate aftermath of what
I honestly believe will go down as the most culturally
significant two weeks in. Yeah. In the history
of Latin music. I don't think that's hyperbole.
I really don't. Maybe even pop music history,
period. I was just about to say that. Yeah. Because
when you look at the sequence of events. It's
just unprecedented. They're barely a week out
from Super Bowl LX. That was February 8th. Right.
It feels like a lifetime ago already. It does.
And we're just days removed from the 68th annual
Grammy Awards. And at the absolute, you know,
the epicenter of this perfect storm is one man.
Benito Antonio Martinez Ocasio. Better known
to the entire planet as Bad Bunny. The biggest
pop star in the world. And that's not just a
talking point anymore. It's a statistical fact.
Right. I know people throw that title around
all the time. You hear it for Taylor. You hear
it for Beyonce. And they're giants, obviously.
And of course. But when you look at the raw data.
The streaming numbers. And more importantly,
when you look at the cultural saturation we have
just witnessed. It's just undeniable at this
point. It is. And what makes this whole story
so compelling, so fascinating, is the journey
to get here. Because we aren't talking about
someone who was, you know, groomed in a Disney
lab or a boy band. No. This isn't a dynasty hire.
He wasn't born into the industry. Not at all.
We are talking about a guy who... not that long
ago, was bagging groceries at an Econo supermarket
in Vega Baja, Puerto Rico. And just last week,
he became the first solo Latino to headline a
Super Bowl halftime show. The biggest stage on
Earth. And if that wasn't enough to completely
break the Internet. As if that wasn't enough.
He walks away from the Grammys with Album of
the Year. For a Spanish language record, which
has never, ever happened before. Never. It's
the holy grail. It is the glass ceiling that
so many people in the industry for decades said
could never be broken. Decades. You had artists
like Gloria Estefan, Ricky Martin, Shakira. All
of them came close. They all tried. They all
pushed the envelope. But no one could get over
that final hurdle. And he just walked in and
did it. He did it. So today's deep dive is, well,
it feels momentous. It feels necessary. Our mission
today is to move past the headlines. Right. Beyond
the Spectacle. Exactly. We all saw the Super
Bowl performance. We've all seen the wild outsets.
We know the songs are insanely catchy. But we
need to understand the phenomenon. We need to
unpack the how and the why. How did this happen?
How did all these pieces fall into place so perfectly?
How did a kid from rural Puerto Rico... completely
reshape the global music industry without ever
compromising his language or his culture. That's
the key, without compromising. How did he manage
to change the entire conversation around masculinity
in a culture that is... historically very traditional
machismo culture and frankly the biggest question
on my mind the one i can't wrap my head around
go on how did he become the undisputed face of
american pop culture in 2026 while refusing to
tour the united states for the entire year of
2025 That is the paradox, isn't it? That's the
part we really need to dig into. It is. And when
you look at the stack of sources we have here,
I mean, we've got biographical data, we have
discography reviews, political activism reports
from San Juan, all the coverage of his recent
achievements. You realize this isn't just a story
about a singer. It never is, is it? It's always
bigger. Never. This is a story about identity.
It's a story about politics. It's about the shifting
center of gravity in global culture. What do
you mean by that shifting center of gravity?
I mean that the concept of the mainstream is
no longer exclusively English speaking or American
centric. He proved that. So let's go back. Let's
rewind the tape. Before the Super Bowl. Before
the Grammys, before the billions and billions
of streams. Let's go to Vega Baja. To the Almirante
Subario, to be specific. Right. And this context
is so important because usually when we talk
about the history of reggaeton, the old school
legends, we're talking about San Juan. We're
talking about the metropolis. The city. The concrete
jungle. Exactly. We're talking about Carolina.
We're talking about the housing projects, the
Casarillos. That's the birthplace. That's where
the genre was born. It's gritty. It's urban.
It's deeply connected to the street life. That's
the Daddy Yankee origin story. That's the Tego
Calderon origin story. But Benito, that's not
his story at all. No. He's a country boy. Vega
Baja's on the north coast. It's not the city.
So he wasn't running the streets. Not even close.
His father was a truck driver. His mother was
a retired school teacher. His was a very stable
working class family. He wasn't involved in the
drug trade. He was at home with his mom and dad
and two younger brothers. And this is the detail
that always gets me. The detail that breaks the
stereotype so hard. I think I know what you're
going to say. He wasn't a street kid at all.
He was a choir boy until he was 13. A choir boy?
I love that detail. It's amazing. It is. And
I think that's the first real key insight into
his musicality. Because if you really listen
to his music, I mean, really listen to the melodies
underneath the trap beats. You hear it. You hear
that church influence. You can hear the structure
of hymns and ballads in his chord progressions.
That explains why he's so melodic. Even when
he's rapping in that low drone, there's always
a song under it. Precisely. And he grew up in
this incredibly rich musical environment at home.
His parents weren't just blasting the hot reggaeton
of the moment. Right. They were playing salsa.
They were playing meringue. They were playing
romantic pop ballads from the 80s and 90s. He
talks about listening to Vico C. The godfather.
The philosopher king of Spanish hip hop. The
absolute godfather. But in the same breath, he
talks about listening to Hector Laveau and Marc
Anthony. So he's just a sponge. He's absorbing
everything from the hardest street rap to the
most lush, romantic salsa. He's a total sponge,
but he's also shy. He was a shy kid. There's
this great detail in one of the biographies where
he talks about being really socially awkward.
He wasn't the class clown. He wasn't the life
of the party. He was the observer. The quiet
kid in the corner watching everyone else soaking
it all in. Which brings us to the name, Bad Bunny.
Yeah. I feel like everyone knows the name, but
nobody really stops to think about how weird
it is. It is weird. It's not Killer Bee or Don
Benito or Lil' Ben. It's a bunny. And it comes
from a childhood photo. There was a school event,
maybe for Easter, and he was forced to wear this
plush bunny costume. And he was not happy about
it. He was furious. In the picture, he just has
this look on his face of pure annoyance. He's
plotting revenge on the world. I think I've seen
that picture. He looks so mad. He's so mad. But
here's the kicker. And this is where you start
to see the early signs of his genius. He didn't
choose the name just because it was a funny memory.
He told an interviewer that he chose it because
even back then as a teenager, he thought it would.
market well. Get out of here really. That's a
direct quote. He understood branding before he
even had a career. That's the part that gets
me. He understood differentiation. He knew that
in a sea of guys trying to project this hyper
masculine dangerous image. Right. Calling yourself
a bunny completely disarms people. It makes you
look twice. It's ironic. It's memorable. It was
a brilliant move. So let's fast forward a bit.
He's in college. He's studying audiovisual communications
at the University of Puerto Rico at Arecibo.
He's trying to be a radio host, producer. And
to make ends meet, he's working at the Econo
supermarket. The famous bagging job. It's part
of the legend now. It's the ultimate started
from the bottom story. But I want to talk about
the timeline here. This is around 2016. What
does the musical landscape look like at that
moment? This is the SoundCloud era, and this
is really, really important to understand. Before
this moment, if you wanted to be a Latin music
star, you needed a record label. You needed a
huge marketing budget. You needed radio play.
You needed a gatekeeper to say yes. Yes, you
needed a gatekeeper. But SoundCloud just blew
the doors off the whole system. It changed the
plumbing of the industry. Completely. It democratized
distribution. All you needed was a laptop and
a Wi -Fi connection. So Benito was working a
shift, bagging groceries, dealing with customers.
And then he goes home and he makes beats on his
computer and starts uploading these tracks himself.
Exactly. And in 2016, he releases a track called
Dials. And Dials isn't just a song. It's like
a match in a powder keg. It just catches fire
online. It spreads like crazy through the underground.
And it's technically Latin trap, which is a bit
different from reggaeton. Could you explain that
difference? Sure. Reggaeton has that very specific,
iconic dembow beat, that boom -boom -chick rhythm.
Right. You know it when you hear it. Trap is
different. It's slower, deeper, with these heavy,
booming 808 bass sounds and skittering, rolling
hi -hats. It's sonically darker, more atmospheric.
And dials caught the ear. ear of DJ Lou Ian.
Who is a massive deal in the scene. A kingmaker.
Right. He runs Hear This Music. He hears the
track, sees the insane buzz it's getting online,
and he basically signs Bad Bunny immediately.
No long A &R process. Just, you're with us now.
And then they re -release Dials with a bunch
of huge features. Right. With Ozuna, Farruko,
Archangel. It becomes an official anthem. But
the next song is the one that really defines
him. Soy Peor. Soy Peor. I am worse. And this
song, you have to understand the context. This
isn't a party song. It's not for the club. No,
it's a heartbreak anthem. It's a sad boy anthem
before that was really a thing in the Latin space.
It's about being bitter after a breakup and just
deciding, you know what? I'm going to be the
bad guy now. Because love failed me. Which is
such a universal feeling. We've all been there.
Fine, if you think I'm bad, I'll be the worst.
Exactly. And it just explodes. Suddenly this
grocery bagger from Vegabaha is the undisputed
face of the Latin trap movement. He creates this
entire persona of this sad, hedonistic bad boy.
It was a movement. But here's where my brain
gets stuck. Because we've seen huge Latin stars
before. We've seen Ricky Martin. We've seen Shakira.
We've seen Enrique Iglesias. But the playbook
for them was always the same. You get huge in
Latin America. You dominate the Spanish -speaking
market. Then you do the crossover. The English
album. The live and love you to loca strategy.
Right. You sing in English. You work with...
Big name American producers. You essentially
dilute the sound to make it palatable for a radio
station in like Ohio. You assimilate. That's
the word. You assimilate into the American market.
The bad bunny. Yeah. He just never did that.
He completely rejected it. And this is the second
key insight into his career and probably the
most important one for his global dominance.
He looked at that crossover model and said, no,
thank you. He said, I'm not going to change my
language. I'm going to make you learn mine. That
takes an incredible amount of confidence or arrogance
or a healthy mix of both. I think it's both.
Probably. But look at how he executed it. It
was brilliant. He did collaborate with English
-speaking artists, but he completely flipped
the power dynamic. Talk about I like it. Okay,
I like it. 2018. Cardi B is the biggest new star
in rap. J Balvin is already a global superstar.
And the song goes to number one on the Billboard
Hot 100. A massive, massive hit. But he's rapping
his entire verse in Spanish on it. He makes no
concessions. And then there's the Drake situation.
Oh, Mia. Mia. This is late 2018. Drake is, without
question, the biggest pop star on the planet.
Any other Latin artist would have killed to be
on a Drake song. And they would have bent over
backwards to accommodate him. They would have
sung the hook in English. Of course. That would
be the standard play. So what did Bad Bunny do?
He made Drake sing in Spanish. Yeah, as the ultimate
power move. It's legendary. It's a declaration
of independence. It's him saying, I am the center
of gravity now. I am global, but I am Puerto
Rican first. You want to work with me, you come
to my world. And the song was a huge hit. It
proved his thesis. It completely proved it. The
American audience didn't need the lyrics translated.
They just needed the vibe, the melody, the beat.
It's almost like he realized that in the streaming
era, those old language barriers just don't exist
in the same way. That's it exactly. Streaming
democratized consumption. A kid in Nebraska can
vibe to a Spanish trap beat just as easily as
a kid in San Juan. the gatekeepers at the radio
stations who used to demand english lyrics they
lost all their power so he's riding this incredible
wave he's got the singles he's the undisputed
king of trap but then he decides to drop a full
album and usually trap artists they aren't really
known for cohesive artistic albums it's a single
genre it's the playlist mentality just give me
a string of hits but in late 2018 He drops X100
Pre. And that title is stylized, right? It's
X100 Pre, which is tech speak for poor simpre.
Forever. Right. And the critics and even some
fans were confused at first. Why? Because it
wasn't just hard trap. It was weird. It was all
over the place. One review called it off kilter
creativity. In what way? What were the sounds?
It had pop punk influences like real Blink -182
vibes on some tracks. It had dreamy synth pop.
It had heartbreaking acoustic ballads. It was
deeply experimental. So he was immediately. signaling,
don't put me in a box. Exactly. It established
him as an album artist, not just a hit maker.
He was building a whole sonic world for you to
live in. And then 2020 happens. The year the
world stopped. But Bad Bunny somehow sped up.
It's honestly exhausting just looking at his
output for 2020. He was unbelievably prolific.
He starts the year February 2020 with YHLQMDLG.
I do what I want. The title says it all, really.
It really does. And this was the party record.
It was pure, unfiltered nostalgia. It was a love
letter to the old school reggaeton he grew up
on. He was meant for the clubs, for cars with
the windows down, for backyard barbecues. It
was the ultimate summer album. It came out right
before Summer was canceled. I know. The timing
seemed disastrous. He releases this massive party
record, and two weeks later, the entire world
goes into lockdown. You'd think it would have
killed the album's momentum, but weirdly, the
opposite happened. It became the soundtrack to
the lockdown. It did. People were having parties
in their living rooms to Sephira. It was this
shared cultural experience of clinging to joy
in a scary time. We have to talk about Sephira.
That song. is a masterpiece of chaos. It's insane.
It changes beats like five or six times. It samples
everything from Missy Elliott to classic reggaeton
rhythms. It's like a full DJ set crammed into
one five -minute song. It's brilliant. But he
didn't stop there. Because we were all stuck
at home, bored out of our minds. He drops Las
Cano y Banasalir. The ones that weren't going
to come out. It was a total surprise drop. A
complete surprise. And it was just a compilation
of B -sides, rough drafts, unpolished tracks
from the YHLQMDLG sessions. It felt so raw and
intimate. It felt like he was just giving us
a gift. Yeah. Like, hey, I know you're bored.
Here's some more music to get you through. It
deepened that connection with his fans. It wasn't
a polished corporate product. It was personal.
And he's still not done with 2020. It's Thanksgiving.
We're all in the thick of it. And he drops El
Ultimo Tour del Mundo, the last tour in the world.
And this, this album is the real pivot. This
is a game changer. This is the one that rewrites
the history books. How so? Because it becomes
the first all -Spanish language album to ever
top the U .S. Billboard 200 chart. Again, not
the Latin chart. The main chart. He beat Taylor
Swift. He beat everybody. He beat everybody.
And musically, it was a total left turn. It wasn't
reggaeton at all. It was rock. It was what he
called truck driver music. It was post -punk.
It was indie rock. It was melancholic and had
these fuzzy electric guitars. He was doing this
low, slurry, almost goth rock vocal delivery.
He was completely unafraid to alienate the fans
who just wanted to party and dance. He was basically
saying, I'm an artist and this is where I'm at
right now. Come along if you want. And that willingness
to experiment, to take huge risks, sets the stage
for the big one. The global juggernaut. 2022,
un verano sin ti. A summer without you. I don't
think we can possibly overstate how massive this
album was. The stats and the source material
are just ridiculous. It became the most streamed
album in the history of Spotify. Yeah. Not for
the year. Ever. It spent 13 non -consecutive
weeks at number one on the Billboard 200. That
puts him in the same league as, like, the Frozen
soundtrack or Drake at his peak. It was true
cultural ubiquity. You couldn't leave your house
without hearing Titi Me Pregunto from a passing
car. You couldn't scroll on TikTok without hearing
Mi Porto Bonito. It was a global cultural moment.
It solidified the idea that Spanish language
music wasn't a niche or a genre. It was just
pop music, period. The biggest pop music in the
world. And it was the first Spanish language
album to be nominated for the big prize, Album
of the Year at the Grammys. It didn't win that
year, but it broke down the door. It broke down
the door. And that brings us to the... recent
history, the buildup to this incredible moment
we're in now in February 2026. January 5, 2025.
And this album was interesting because he explicitly
described it as recommitting to Puerto Rico.
What does that mean? After the massive globe
-trotting sound of Unverano, which was influenced
by music from all over the Caribbean and beyond,
this album was a return to his roots. More personal
stories about the island. He turned his gaze
back home. And the marketing was so cool. The
character of Concho. Yes. Yeah. The Puerto Rican
crested toad. The Sapo Concho. It's an endangered
species native to the island. And he used this
cartoon toad character to promote the album.
He used the entire album rollout to raise awareness
for conservation efforts for the toad. It's that
perfect blend of massive commercial reach and
a hyper -local, specific concern that makes him
so unique. And that album, Debbie Tirar Mas Fotos,
is what just won him the Grammy for Album of
the Year last week. Finally, the first Spanish
-language album to ever win the big one. It felt
like the industry finally caught up to the reality
that the fans have known for years. It really
does. But, you know, we're talking a lot about
the music, but we have to... to talk about the
style, the aesthetic, the visuals. Because Bad
Bunny isn't just reshaping what pop music sounds
like. He's reshaping what it looks like to be
a male superstar. especially in latin america
we're talking about the new masculinity exactly
i mean just look at him he wears pink he wears
florals and skirts he's got the short shorts
he paints his nails these long manicured fingernails
and this is so significant because he's coming
from the world of reggaeton and latin trap these
are genres that have historically been absolutely
steeped in machismo right traditional gender
roles are very very strong in that culture you're
supposed to be tough stoic The alpha male. And
here comes the biggest star in the entire genre,
performing in full drag for the music video for
Yoperio Sola. That video was a cultural earthquake
when it dropped. It was. And he wasn't just,
you know, wearing a wig for a laugh. He was in
full prosthetics, makeup, heels, everything.
He was embodying the woman in the song who is
declaring that she wants to dance alone, free
from harassment. It was such an incredibly bold
move. It was. And he wasn't doing it as a joke
or for shock value. He was challenging the very
foundation of those norms. He was saying, I can
be the most successful artist in the world and
I can do it in a skirt. He was the first man
to appear solo on the cover of Playboy magazine
other than Hugh Hefner himself. Think about that.
He is actively and deliberately dismantling the
archetype of what a reggaetonero is supposed
to look and act like. And it goes beyond just
fashion choices. It's about genuine allyship.
I remember the incident with Alexa Negron Luciano.
Yes. A transgender woman who was brutally murdered
in Puerto Rico in early 2020. It was a horrific
hate crime. She was homeless. She was mocked
on social media, hunted down and killed. It was
a moment of deep national shame and soul searching
on the island. It was awful. And Bad Bunny goes
on The Tonight Show with Jimmy Fallon, one of
the biggest platforms in America. And he performs,
but he's wearing a T -shirt that says in Spanish,
They killed Alexa, not a man in a skirt. That
is such a powerful, unambiguous statement to
make on national television. He used his platform
to correct the disrespectful narrative, to honor
her identity, and to call out the transphobia
that led to her death. It was a huge moment.
And it's why Ricky Martin, who is an icon in
his own right, has called Bad Bunny an icon for
the Latin queer community. That's high praise
coming from Ricky. It is. And he's been open
about his own identity, too. He famously kissed
a male backup dancer during his performance.
Exactly. He's creating a space for his fans,
especially young men, to be themselves. He's
signaling that the old rigid rules just don't
apply anymore. Speaking of rules and breaking
them. We absolutely have to talk about his politics
because usually when an artist reaches this level
of fame, when you're a corporate friendly Super
Bowl headlining superstar, you tamp down the
political stuff. You play it safe. You don't
want to alienate half of your potential audience.
Right. You become Switzerland. Bad Bunny does
not subscribe to that theory. In fact, he seems
to get louder and more politically engaged the
bigger he gets. His relationship with Puerto
Rico. the island, the politics, the struggles.
It's absolutely central to who he is as an artist.
It goes all the way back to Hurricane Maria in
2017. He was one of the most vocal critics of
the government's failed relief efforts. But the
real turning point was the summer of 2019. The
Telegramgate protests. Yes, when nearly 900 pages
of private Telegram chats between Governor Ricardo
Rossello and his inner circle were leaked to
the public. And the contents were just... Vile.
Beyond vile. They were making homophobic jokes,
misogynistic comments about female politicians
and worst of all, making light of the dead bodies
that were piling up in the morgues after Hurricane
Maria. And the island just erupted. Spontaneously.
It was a peaceful revolution. Hundreds of thousands
of people in the streets and Bad Bunny. He literally
put his massive European tour on pause. He was
in Spain, I think. He was. He canceled shows,
flew back to Puerto Rico, and he joined Residente
and Ricky Martin in the streets. They led a protest
that shut down the Expresso Las Americas, a major
highway in San Juan. Can you just imagine that
scene? The biggest pop star in the world standing
on a highway, shouting through a bullhorn, demanding
that the governor resign. And it worked. Locello
resigned. It was the first time in the history
of Puerto Rico that a governor was forced out
of office by popular protests. And during the
protests, they released that anthem, Afalanda
Los Cuchillos. Sharpening the Knives. Okay. Which
was not a pop song. It was raw, unfiltered political
rage set to a beat. And he hasn't stopped since
then. The music video for El Apagón from Un Verano
Senti. It wasn't just a music video. No, it was
a 22 -minute documentary. It was straight -up
investigative journalism. It was. He turned his
platform over to the independent journalist Bianca
Graulao to report on the real -world issues behind
the song's title, The Blackout. They reported
on Omame Energy, the private company that took
over the island's power grid, and the constant
blackouts that were plaguing the people. And
they went deeper. They reported on Act 22, these
controversial tax breaks that encourage wealthy
foreigners like crypto investors and YouTubers
to move to the island. And in the process, they
drive up real estate prices and displace local
Puerto Ricans. It's classic gentrification. He's
using his biggest music videos to educate the
world about the modern day effects of colonialism
on his home. Which leads us to the 2024 election
and the drama that spilled over into 2025. This
is where the story gets really intense and where
we see the setup for this current historic moment.
It does. During the 2024 election cycle, there
was that infamous Trump rally at Madison Square
Garden. Oh, I remember this. A comedian opened
for the rally and called Puerto Rico a floating
island of garbage. The backlash was immediate
and fierce. And Bad Bunny didn't stay silent.
He went on social media and endorsed Juan Dalmau
of the Puerto Rican Independence Party. Which
is a huge deal. That's a shift away from the
two traditional establishment parties on the
island. It's a radical statement. And he directly
criticized Trump for allowing that kind of rhetoric
at his. event. But it didn't just end with a
tweet. This controversy spilled over into his
touring decisions for the entire next year. And
this is the part that still blows my mind. In
2025, Bad Bunny did not tour the United States.
Stop and think about the economics of that for
a second. His last major tour, the world's hottest
tour in 2022, was the highest grossing tour of
the year. He grossed hundreds of millions of
dollars. So he looked at a guaranteed nine figure
payday and just left it all on the table. Why?
What was his reasoning? He publicly cited concerns
that U .S. Immigration and Customs Enforcement
would target his undocumented fans at his concerts.
Can you unpack that? What does that mean? Well,
his concerts are massive gatherings of Latinos
from all backgrounds and with all kinds of immigration
statuses. He was worried, based on the political
rhetoric at the time, that these concerts could
be used as traps. That ICE could show up and
use the events to profile and detain people?
Exactly. So he looked at the potential risk to
the most vulnerable members of his fan base,
and he said, I'm not doing it. I won't put them
in that position. That is truly putting your
money where your mouth is. That is a level of
integrity you almost never see in the entertainment
industry. It's a monumental sacrifice for his
principles. So instead of a huge U .S. stadium
tour, what did he do in 2025? He went home. He
did a 30 -date residency called No Me Quiero
Arde Aki, I Don't Want to Leave Here, at the
Chiliceo Arena in Puerto Rico. So he played for
his people. He played for his people, and he
did a stadium tour of Europe and Latin America,
but he completely bypassed the U .S. mainland.
It sends such a loud message. I will perform
for my community, but I refuse to let my art
be a tool for their persecution. It was a very
powerful, very expensive and very visible form
of protest. And while all this is happening,
he's still doing the philanthropic work on the
island. The Good Bunny Foundation? Yeah. The
Bonita tradition holiday gift drives every Christmas.
He's there in person handing out toys, musical
instruments, art supplies to thousands of kids.
And he partnered with Mark Anthony to rebuild
baseball fields for youth leagues. Right. A $1
.6 million project. He's deeply personally invested
in the infrastructure and the future of Puerto
Rican youth. Okay. So we have the artist. We
have the fashion icon. We have the activist.
But we also have to talk about... The Wrestler.
The Wrestler. This is my favorite subplot in
the entire Bad Bunny saga. It's just wild, because
usually when a celebrity does a guest spot on
WWE, it's, well, it's a little embarrassing.
It's cringeworthy. They stand there, they wave,
maybe they throw a soft punch that looks terrible.
Right. But Bad Bunny is legitimately good, like
technically proficient in the ring. He's amazing.
He's doing Canadian Destroyers off the top row.
He's flying through the air. He's a lifelong
fan of professional wrestling. You can tell he
respects the business. And he trained incredibly
hard. Oh, absolutely. He debuted at WrestleMania
37 in a tag team match, which was already impressive
enough. But then he came back for the Royal Rumble.
And he eliminated Sheamus and Dolph Ziggler.
Two former world champions. He eliminated Sheamus.
It's incredible. But the absolute peak was Backlash
2023. In Puerto Rico. The first WWE premium live
event on the island in almost 20 years. And he's
in the main event, a San Juan street fight against
his friend turned rival Damian Priest. I watched
that match. The crowd noise was. deafening it
sounded like a jet engine for 25 straight minutes
the passion was unbelievable and he took real
bumps he got chokeslammed through a table he
was hit with kendo sticks and he used trash cans
and chairs it was a brutal incredible match and
he won It cemented his status, not just as a
fan, but as a legitimate performer who is willing
to put his body on the line for the sake of entertainment.
It earned him so much respect from the wrestling
community, which is notoriously hard to please.
It just adds to this mythology around him, this
idea that he does everything at 110 percent.
If he's going to design sneakers with Adidas.
They're going to be the most sought after, instantly
sold out shoe of the year every single time.
If he's going to model for Calvin Klein. The
2025 campaign is going to generate $8 .4 million
in media impact value in the first 48 hours.
He's a brand powerhouse. Which brings us to today.
To? Right now. Yeah. The summit. Yeah. 2026.
The convergence. Where all these different threads,
the music, the politics, the brand power all
come together. So he spends all of 2025. refusing
to tour the U .S. and protest. He's effectively
boycotting the American concert circuit. But
then it's announced that he is the headliner
for the Super Bowl LX halftime show. And immediately
there's a political firestorm. Donald Trump calls
the choice ridiculous. He's tweeting about it
constantly. But on the other side, you have Jay
-Z's Roc Nation, who produces the show, and the
NFL itself. And they stand by the choice. They
stand by it firmly. And Bad Bunny accepts the
gig. Now, some people on the outside might say,
wait a minute, you won't tour the U .S. because
of ICE, but you'll play the Super Bowl. Isn't
that hypocritical? That's the obvious question.
But you have to look at how he framed it. He
explicitly viewed accepting the gig as a form
of protest in itself. A protest? How so? He saw
it as infiltrating the system. It was a Trojan
horse strategy. His goal was to stand on that
stage, the biggest, most watched stage in America,
the ultimate symbol of American capitalism and
culture, and perform a show that was unapologetically,
overwhelmingly in Spanish. He wanted to force
128 million people. To listen to his language,
to see his culture on his terms. Precisely. And
that is exactly what he did on February 8th.
He didn't water it down. He didn't bring out
a bunch of English speaking guest stars to make
it safe for the audience. No, he brought Puerto
Rico to the Super Bowl. He had the planeros with
the drums, the dancers, the aesthetics of San
Juan. It was a cultural statement. And the impact
was instantaneous. His entire back catalog surged
on the charts. His songs reentered the Hot 100.
And the governor of California, Gavin Newsom,
officially declared February 8th, 2026 as Bad
Bunny Day in the state. It was the ultimate flex.
It was him saying, I can. boycott your entire
tour circuit i can stand against your government's
policies and i can still come here and dominate
your single biggest cultural event on my own
terms and then just one week later just a few
days ago he walks into the grammys and wins album
of the year for debbie tirar mas photos the trifecta
He's finally done it. He has the critical acclaim
with the Grammys. He has the commercial dominance
with Spotify's most streamed artist globally
for four separate years, which is a record. And
he has the cultural credibility with the activism,
the fashion, even the wrestling. it's just incredible
he's achieved what everyone thought was impossible
he's the biggest star in america and he barely
has to speak english to us and that's the paradigm
shift that's the core takeaway from this whole
deep dive he proved that global success is no
longer dependent on assimilation into the american
market you don't have to change who you are you
don't have to become american to conquer America.
You can be unapologetically yourself, unapologetically
Puerto Rican, and the world will come to you.
So what does this all mean for the future? I
mean, where can he possibly go from here? He's
reached the summit of the mountain. That is the
million dollar question, isn't it? He's won the
awards. He's played the Super Bowl. He's fought
the political battles. And he's still so young.
He's barely in his early 30s. He is. But I think
the central tension of his career remains. And
that's what will define his next chapter. And
what's that tension? It's the friction between
being completely integrated into the machinery
of US pop culture, while at the same time remaining
one of the most steadfast and vocal critics of
US politics and policy, especially as it relates
to Puerto Rico. The paradox of being an icon
in the empire while constantly critiquing the
empire. Exactly. How does he navigate that? How
does that relationship evolve now that he is,
for all intents and purposes, a pillar of that
very pop culture? critiques. It is going to be
absolutely fascinating to watch. Will he finally
tour the U .S. in 2027? Does he get even more
political? Could he one day run for office in
Puerto Rico? At this point, I would not rule
anything out. Well, if you haven't listened to
Debita Armas' photos yet, you need to go do it.
But listen to it with all this context, with
fresh ears. Know the history, know the struggle,
know the protest, and know the ultimate triumph
that exists. behind every single beat. It completely
changes the way you hear the music. It really,
really does. Thanks for diving in with us today.
This was a big one. It was. Take care. We'll
catch you on the next deep dive.