Operation Desperado: The long con of Vivek Ramaswamy
It only takes one compliment to get the former presidential candidate to speak to your favorite football team. What happens next is entirely up to you.
A high-ranking member of the Patriots Caucus messaged me in April. “Hey, check this out,” they said.
The picture was a text exchange with former presidential candidate Vivek Ramaswamy and an unknown third party posing as Ohio State head football coach Ryan Day.
I love little exchanges that show searing insight into someone’s mind. Here, we see that the 39-year-old Ramaswamy is susceptible to phishing attacks as long as you compliment him.
I didn’t know what to do with the information other than laugh. Of course, Ramaswamy, ostensibly cut from presidential timber, thinks that Day would not only personally text him to arrange such an affair but that he’s also the type of guy to sign his text messages.
A few months later, I showed the exchange to a high-ranking Republican member of the Patriots Caucus. Not that I had any reason to doubt my friend, but I asked if that number belonged to Vivek. After all, it’s not out of the realm of possibility that my friend had gotten bad information along the way.
“Oh no,” the Republican assured me. “That’s Vivek’s number.”
I can thank this business for giving me a new kink centering around when politicians show me that they are even dumber than I initially thought.
I still didn’t act on the information, as I didn’t know what to do. Though my friend’s mysterious accomplice had fooled Ramaswamy, I didn’t feel comfortable impersonating Ohio State’s head football coach.
But then, on a random Monday afternoon when I got bored—boredom is the Devil’s Workshop, as they say—I decided to text Ramaswamy using an old alias from my college days: Tim Chitters, a name which I promptly misspelled in my haste.
Ramaswamy responded almost instantly.
There should have been some red flags here. I intentionally used “OSU” instead of “Ohio State.” I intentionally referenced “the head ball coach” instead of Ryan Day.
Most importantly, the clearest red flag was that I said “a lot” of Ohio State football players not only have opinions on the 2026 Republican gubernatorial primary, but they wanted him to join the mix.
I even tried to make the ruse obvious by adding a gratuitous “if you can believe that.”
But the first thing to understand about Ramaswamy, other than he reportedly earned his fortune through various pump-and-dump schemes, is that he’s a raging narcissist.
In his defense, I probably would be, too, if I had cheated my way to vast wealth before turning 40. But I didn’t, and in this case, Vivek’s swollen ego was the bait in which I hooked him into the scheme.
In his mind, why wouldn’t a group of young athletes want him to run for governor in 2026?
I’ve learned in this business that you can make magic happen by directly going to the bosses, paying them a compliment, and having them offload you to one of their many gremlins.
It’s precisely how I got Frank LaRose’s disastrous Senate campaign to name a fictitious Baptist preacher as his Miami County Campaign Chairman.
If you go to the assistants, they will most likely try to vet you for the sake of their jobs. Had I gone to Ramaswamy’s assistant, she would most likely have at least tried to Google something like “Tim Chitters Ohio State football” and not found anything to confirm his existence.
She might have even discovered the fake profiles I created when I routinely drank FourLoko and began asking how much she knew about this shady character pretending to represent the famous local football team.
But if you go to the boss, and the boss spins you off onto the employee, it’s not like most employees have jobs because they routinely ask critical questions.
From there, it became a matter of not seeming desperate to get Ramaswamy into the waxing zone.
Again, that I was attempting to arrange to meet Ramaswamy at a famous chicken shack off Olentangy Road should have been another blaring siren that something was amiss.
But that’s the magic that can happen when the boss pawns you off to the employee.
The hardest part was keeping my mouth shut between August 5th and August 23rd, which, as anybody who knows me can attest, is quite challenging for a first-ballot Hall of Fame yapper such as myself.
On the eve of the event, I contacted Ramaswamy’s assistant to ensure that we were still a go.
Later that night, I got nervous about Ramaswamy appearing at the appointed time and place because he decided to travel to Chicago to agitate pro-Palestine activists for some reason known only to himself and God.
Those activists promptly drummed him out of the park with chants of, “Racist, go home!” but not before he bought a Trotskyist newspaper for $5:
As others have remarked on Twitter, it’s a little too on the nose to see a Trotskyist confront a technocratic fascist like Ramaswamy by peddling him a newspaper. But I digress.
The worry that Ramaswamy wouldn’t make the meet was misplaced. That man was up at 9 a.m. thinking about what he wanted to say to the local football team.
We know that because my friend texted me with a major scoop, or so he thought, that Ramaswamy was somehow meeting with Day on Friday.
We know this because my friend had been sent a screenshot of Ramaswamy responding to the Google Voice number ostensibly belonging to Day:
You can probably imagine the awkward place this put me in. I had to explain to my friend that I was well aware Ramaswamy thought he was meeting the head football coach on Friday because I had taken the joke to the extreme, as I’m wont to do when I get bored and am presented with such opportunities.
A couple of hours later, my friend sent me new screenshots from the source, which, again, is neither of us:
This is where Ramaswamy’s lack of football knowledge came back to haunt him. Had he even had a passing familiarity with local football, he would know that August is a particularly grueling time for head coaches trying to wring every drop of preparation out of their team before the season's long grind.
Day would not be idly texting like this. He, like Ramaswamy, has a team of minions hired to handle such menial tasks. But again, it goes back to Ramaswamy’s ego. Why wouldn’t Ohio State’s football coach want to text with a guy who recently had a ridiculous run for president?
By this time, I knew that nothing was stopping this train. Ramaswamy would be appearing in the parking lot of that famous chicken shack off Olentangy Road.
I had expressed my desire to his assistant that the list of people be kept to Ramaswamy and her due to the limited space in the athletic facilities (read: my desire to interact with as few people as possible).
Again, it was a normal request that most people would have honored. But not Ramaswamy! About an hour before our meeting, I got a call from a 917 number. Not knowing if this was a call related to Ramaswamy or something related to my business as a political gadfly, I answered with a simple “Hello.”
It was some guy named Kevin. He said he and Ramaswamy’s entourage would soon be heading my way. How many people was he bringing? I asked. I only had clearance for one other person.
Kevin said he’d send me a list. I promised that I would “see what I could do.” Minutes later, he sent me a list of five names:
This gaping asshole, I thought about Ramaswamy. Of course, he wants to bring as many people as possible to show what a big and important person he is.
I wasn’t worried about most of the names on that list. A quick Google search showed that they appeared to be civilians working in the medical field.
But I was concerned about this Kevin character because he billed himself as some security figure—and you never know how guys like that will act or what kind of steroid regimen they might be on.
But I didn’t have much time to think, as I soon received another text from Amanda the Assistant.
Jesus! Nobody had said anything about an intern being in the mix, but I had no choice now. The con had to continue just a little bit longer.
Funnily enough, the intern made me the most jittery of all the people in Vivek’s entourage. I thought, at least for a second, that he might have recognized me from one of my many TikTok videos of calling some state legislative backbencher a pervert.
And it’s not like I was wearing any officially licensed Ohio State gear, either. Just a generic “Ohio” polo provided to me by my business partners at Supporter Supply, the finest apparel company in Columbus.
If the intern had any reservations, he never voiced them. We had a nice chat. What did an intern do for Vivek Ramaswamy, anyway? “Whatever they need done, pretty much,” he and the Assistant agreed. Friday was actually the intern’s last day of employment with Ramaswamy.
“Well, it will surely be memorable,” I joked.
Minutes later, Ramaswamy ended the suspense and graced us with his presence. You can view our entire interaction, completely unedited, in the video below:
My only goal was to get a picture with Ramaswamy, to show people just how far you can take these self-proclaimed leaders of men by simply paying them a compliment—in my case, it was the idea that the local football team had a Ramasway for Governor Caucus.
And now here he was, the man with an ego swollen enough to run for president despite having zero political experience, meeting an obscure blogger in the sweltering parking lot adjacent to a famous chicken shack.
“John, was it?” Ramaswamy asked, barely interested in the man he viewed as a peon.
No, I corrected him. It’s Tim. A name that he’ll probably never forget.
Honestly, I had plans to see how far I could get Ramaswamy to go on camera. But I didn’t want to risk being made in front of an alleged security professional.
You never know how people will react in the moment when they realize they’re being embarrassed, especially the types of people who get paid to do violence for rich people. It’s not like you need a license to carry a concealed weapon in Ohio, either.
So, I kept it light and asked him a few normal questions. Perhaps the most bizarre anecdote came when Ramaswamy said his neighbor, a former walk-on under then-head coach Urban Meyer who never saw the field during a game, still wears his Rose Bowl ring when he mows the lawn.
That would be… something, for sure. But Ramaswamy also all but admitted that he never cared about the local football team… until he realized how to use them to further his political career.
My only goal was to get out of there without being accosted. That’s precisely what I did on my bicycle, which, as I explained to the entourage, I was riding thanks to the gas prices in Joe Biden’s economy.
Initially, I had contracted another high-ranking member of the Patriots Caucus to stand outside the athletics facility, hoping to get a video of Ramaswamy looking dumbfounded when he couldn’t simply breeze into the building.
That patriot, however, could not make it due to circumstances outside our control.
I would have captured that footage myself, but again, I didn’t want to risk a kerfuffle with his security gremlin. But it didn’t take long for the calls and texts to start.
Amanda the Assistant—was her name actually Jeanine? I had no time to ponder such betrayal by a confidant.
I was too busy hitting Ramaswamy with what has become the calling card of the Patriots Caucus in such moments: An (uncensored) picture of Shrek’s penis.
The message landed almost instantaneously with Ramaswamy’s last-ditch effort to contact the Google Voice number he believed to belong to Ryan Day:
My only regret is that I couldn’t obtain a video of Ramaswamy reluctantly explaining to his entourage that they would not get a unique behind-the-scenes look at the local football team thanks to his burgeoning career as a right-wing grifter.
But even in those frantic moments, Ramaswamy couldn’t even humble himself to contact the only guy he had met. He still clung to the illusion that he was personal friends with the head football coach; that surely, he had not been bamboozled. His friend would undoubtedly be along any minute to save them from the trophy room.
Well, hopefully, Ramaswamy got a good look at those trophies.
Given his political instincts and knowledge of one of Ohio’s most sacred institutions, it’s probably as close to a trophy as he’ll get for the rest of his life.
THOSE WMDs. How to build a 500-ton forging press… The death of an adjunct… Nine smart ways to slash your grocery bill… The staggering death toll of scientific lies… Why exactly does my hair hurt?
Wow wow. Come for the remarkably in-depth reporting on Ohio Statehouse matters, stay for the long cons of aspiring carpet baggers. This is an all timer
Love to see what my subscription to the Rooster makes possible! Fantastic.