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A 16-Year Old Security Guard For Celebrities: My First Derby


My first Derby story is unlike many first Derby stories. Nearing the first Saturday in May of 2008, I was in the middle of my, let’s call it a “rambunctious” phase.  A 16-year old neighborhood rabble-rouser, I got into so much trouble desperately searching for beer during Spring Break that my parents gave me a grounding like never before — double super secret probation until after Memorial Day Weekend.

It was harsh, but just.  Luckily my parents were kind enough to find things to keep me busy. Plenty of lawns were mowed, stacks of dishes washed and countless carpets cleaned. With Derby around the corner, they weren’t going to miss the festivities to keep a watchful eye on me from home. The solution? Brantley Security Services, the security services you need in situations like this.

It was my only chance to do anything at all on the sacred first weekend of May. The $13 an hour was just an added bonus.

An Early Start

Before Churchill Downs was picked up by its ankles and shaken full with people on Derby Day, I got a head start on learning how to stand for 12 consecutive hours by logging time on Thursday (Pre “Thurby” era) and Oaks Day.  I knew I wouldn’t get any action on Thursday, and Friday was a disappointment.  Saturday better not suck if I was going to arrive at 6:00 a.m. in my uncomfortable black dress shoes and ill-fitting red vest.

The only good news was my detail. I remained inside throughout my three-day trip, but they saved the best for last. Three years removed from the $121 million expansion, I didn’t mind the hidden spires if I got to “work” as the primary police for entering the Matt Winn Dining Room.  Named after Churchill’s most famous president, its third floor location was right in the middle of the upper class madness.

Matt Winn was quite the ladies' man.

Matt Winn was quite the ladies’ man.

It didn’t take long to learn the politics of the track. During my waiting-around time before the gates opened, I did a little exploring up the escalators. Millionaires’ Row gets all the hype because of the name, but that’s where the new money goes to show off.  People sit in Millionaires’ Row to tell others they are sitting in Millionaires’ Row.  The old money is further upstairs in the Jockey Club Suites, where there are more $100 minimum wager windows than regular windows because they ain’t got time for that. The Matt Winn room lies in between. It’s F-U money that doesn’t like to say F-U loudly and would rather eat a few good meals and place premium wagers, rather than booze their brains out.

The best part about the Matt Winn room is that it’s adjacent to the elevator that takes patrons to the Turf Club. The turf club is THE place to be. It’s where the athletes go to be filthy rich athletes. It’s the kind of place that makes Wes Welker want to make it rain upon exiting. It’s the kind of place where you can see the coolest of the coolest.

I didn’t realize how much money was being thrown around until I met my favorite old man. He was a rather large man that walked with a dip, supported by a cane with a face that was partially hidden by a straw hat, depending on how he was feeling. We’ll call him Mr. Cane. I exchanged pleasantries whenever possible, how else was I going to make extra money on tips? Even though he didn’t get around quickly, he arrived early and never sat still for long.  I thought my kind words would help me earn my first tip.  Then a tip literally fell onto the floor.

Mr. Cane was halfway down the hall, heading toward the Turf Club when I saw the manila envelope fall from his back pocket. “Sir, you dropped this,” as I half-jogged to the slow mover. He was relieved, “Can you imagine what my son would’ve said if I lost his $10,000?” HELL NO I CAN’T IMAGINE BECAUSE I’VE NEVER SEEN $10,000 IN MY LIFE.

Did my generosity earn any of that $10,000? No. Should have I expected a financial reward for a simple act of kindness? No. But damn it, how else was I going to get tips? I continued showing generosity throughout the day, but it often failed to provide the monetary assistance I so yearned for.

A First Encounter

Mr. Cane’s early presence was uncommon. Few people rush to get to the track for bloody’s and breakfast. They’re too hungover from the red carpet Derby Eve Galas. By 10:00 am the place started buzzing as I anxiously awaited for my first celebrity sighting. What was I hoping for? Pretty much anything. As a 16-year old that had just finished going through my growth spurt, standing for more than 12 consecutive hours was hell. To make matters worse, the breaks to eat were not enough. I needed a meal about every two hours. Instead the devil’s pitchfork poked my belly all damn day.

I digress…let me tell you about what I was actually hired to do. As the gatekeeper of the Matt Winn Dining Room, my task was simple — ask for tickets and check for pink wristbands.  Simple.  They must have both upon first entering. If not, they’re S.O.L. Sorry, you can’t come in. Lucky for me, that was never an issue. I spent my time charming while looking at people’s wrists and asking for tickets, hoping for the people-watching to pick up.

Finally, something cool/weird happened. Not to me, to the boy scout covering the indoor suites to the left of the my position in front of the dining room. He was the first on the floor with a celebrity encounter, but the kid (no more than 14 years old) asked former heavyweight champion Lennox Lewis for a picture, except he didn’t say that; he asked Mr. Evander Holyfield for a picture. He could have called the enormous human being a variety of offensive names, but nothing would have been more insulting than confusing him with his rival.  Luckily, Lewis shrugged it off, laughed and obliged.  I took the picture, and the biggest man I had ever seen let out one of the biggest smiles I had ever seen.

You probably still don’t understand how massive Lennox Lewis was, so let me restate this — he’s the largest human being I’ve ever laid eyes on.  I thought I was a big guy at 6’6”, but Lewis probably had 2 inches on me with the dreads. I got a handshake after taking the picture and let out an involuntarily “holy shit.” This kind of reaction would become common throughout the day.

Secret Service

The instructions I received to become a teenage security officer were pretty simple. I got a vest, was told which color I could allow into my room and was handed a color-coded piece of paper as my “guide to being a security guard.” Kept in my rear left pocket, it had the colors of each different area and who could get in where. Only a few had clearance to go anywhere, definitely not those arrogant SOB’s in Millionaires’ Row (but it sure was glorious to tell them “No, you’re not allowed in here”). However, few guests tried to slide into the Matt Winn room without a pass, so it wasn’t of a problem.

My first problem was nearly a nightmare.

Naturally when guests sit at a dining room, they fill a table with eight people. As one party entered, there was usually a little bit of chaos as I checked them all in. After about 30 seconds of back and forth schmoozing, I’d try to slide a betting tip in there and wish them a good day. I’m certain there was at least one occasion when a big group of Italians snuck a few passed me behind their BS niceties.

Then I encountered a group without anything. No wristbands, no tickets, no lanyards holding tickets. Nothing. The men in suits in suits surrounded two women. One was a dark-skinned, dark-haired bombshell in red. The other wore a plain gray dress, with a wide low-hanging gray hat to match.  Even though her face was partially covered, she reminded me of Renee Zelwegger in “Me, Myself, and Irene.”

As they approached my territory in front of the door, the women never flinched, continuing their gossipy, giggly conversation as I asked, “Ma’am, may I see you wristbands?”

I was met with an open-palm to the chest. “They’re fine,” a suited-man instructed me, never breaking stride. I was speechless. I turned around with my arms up, dumbfounded as to what to do next. I asked the guy manning the elevator to my right, “what was that?”

He responded by pointing to his left pec. “You see the pin?” My face must have only looked more perplexed by the response. “Secret service.”

My friend Will was more familiar with their kind and knew a Secret Service pin when he saw it.  It was the ultimate, “Don’t F with me” mark in society that I had never seen before. It was also a mark conveniently left off of my rear left pocket reference sheet. Thanks a lot Brantley. After debating for an hour or so as to why Secret Service was there, a scheduled bathroom break across the hall from out stations revealed that the woman in gray was Ms. Chelsea Clinton, Matt Winn’s most famous patron for Derby 134.

Chelsea's red carpet appearance at Derby 134 from Garry Jones of the AP.

Chelsea’s red carpet appearance at Derby 134 from Garry Jones of the AP.

MP’s Don’t Play

At this point in the story, you’ve read 1,400 words and you’re ready to stop when you see that Lennox Lewis and Chelsea Clinton are the most famous people involved so far. Don’t worry, it’s about to go into fifth gear.    

Before I go any further, I must discuss my relationship with my elevator-guarding friend, Will the MP. Will spent his first weekend of May each year with his MP group from Ft. Knox, raising money for their annual ball. It only took two days for his company to raise enough money to party their asses off once a year.

I learned a lot from Will. For the first time in my life, I was talking to an active member of the military. I got some perspective I’d never encountered before, helping me understand and respect the sacrifice. It wasn’t just the cool stuff MP’s got ahold of (even though we did spend a solid 30 minutes talking about anti-lethal riot weapons), it was stuff like, “don’t lock your legs or you could pass out.” If he had not told me that my tall ass would’ve passed out at least once.

Will was great. Not only did I have a buddy 10 feet to my right to shoot the ish with when we had hours of downtime, I had somebody with a spine to help my softside. I’m not ashamed to say that I was hesitant to be an enforcing security guard. I’m a lover, not a fighter. Will lived by rules, and by god they were enforced.

The beautiful part about his job specifically is that his elevator was the gateway to a variety of places: the Matt Winn room, the indoor suites and the Turf Club. It didn’t matter who walked out of those elevator doors, if they didn’t have their tickets and their wristbands, they weren’t going any farther. That’s exactly what happened when Terrell Owens walked through the door.

T.O. was an astounding physical specimen in his gray suit. You don’t expect wide receivers to be 6’6” yet the best of the best was taller than me. At first I was taken aback. This is when T.O. was T.O.; before he was a reality TV star, he was the Cowboys’ best receiver, arguably the best in the NFL. He was surrounded by a dude that was either Kimbo Slice or Rick Ross or just another big black guy with a big bald head and a massive beard, I’ll never know. He had a handful of beautiful women as his shield in front, with one acting as a de facto tour guide. When Will the MP asked where their tickets and wristbands were, she only had a sheet of wristbands to show.

Will the MP was Team NFs before Team NFs was a thing. He didn’t care that it was T.O. That guy didn’t have tickets and a wristband, so he wasn’t getting to the Turf Club. I approached the barricaded area to act as a second wall. I meant to look like a badass, but I was really just trying to do my best to miss zero parts of this astonishing situation. T.O. was pissed. The beautiful tour guide was forced to go back downstairs to fetch their tickets in order to get through. We stood with our hands folded at our waste to assert our authority, while an aviator-adorned and angry T.O. cussed under his breath to Kimbo/Rick Ross/big black bald bearded man.

When T.O. couldn't keep to the Turf Club.

When T.O. couldn’t get to the Turf Club.

The standoff lasted a solid 15 minutes, maybe more. Rich people with their fancy camera phones came by to take pictures. T.O. begrudgingly offered smiles, until he got too impatient for me and Will the MP. Finally the woman returned with the tickets, allowing T.O. to advance to the Turf Club.

Movin’ On Up

The chaos surrounding the stoppage of T.O. appeared to be the climax of the day, but there was a lot more Derby to be done.

A slew of other celebrities would pass through our area throughout the day. Nobody was more kind than the late Anna Nicole Smith’s babby daddy. Fresh off a paternity custody victory, the soul-patched and frosted-tipped Larry Birkhead passed through with baby Dannielynn. A nice guy, he shared a few words with us before heading to his final destination. UofL’s former star center, David Padgett, walked by fresh off an Elite Eight appearance. I had seen Shagari Alleyne throw down dunks at Freedom Hall against Austin Peay, but I never realized how massive a 7-footer actually was until I stood next to Padgett. But those two were just the pre-lims.

The day seemed almost done around 3:00, even though we were still three hours from Derby post-time. A middle-aged man with a Nikon around his neck was walking around the area, examining each picture and piece of art closely, until he neared the entranceway to the Matt Winn room.

“Can I help you?” I asked the gentleman. He was a horse guy, a part-owner of the Derby longshot Denis of Cork. The gray horse barely made it into the field, but he didn’t care, he was just happy to be there. He told me was a relative of Matt Winn, and just hoped to look around the room named after his kin. I was happy to oblige, and he was happy to give me a cork, emblazoned with the horse’s silks. That was more than enough to give me a “Derby Horse,” a tip that I would give to people going in and out of the room.

Unforuntately, Denis’ owner distracted me from the greatest celebrity sighting I would ever behold — Hugh Hefner and the Girls Next Door. I caught a fleeting glimpe as they passed through to the Turf Club when I heard someone shout, “HEY HEF!” I saw him wave, with his beautiful reality star girlfriends in tow. Shielded by their massive hats, I was disappointed to only catch a glimpse. But, the best was yet to come.


Approximately 30 minutes later, my boss lady came by. Looking for people to rotate as others took their lunch break, I was competent enough to earn a temporary promotion. She moved me upstairs to the Jockey Club Suites.   I was placed in front of the Aristides Suite, named after the Derby’s first champion. What I saw was overwhelming, but I had to play it cool.

The Aristides Suite was reserved for the big wigs. Paul Hornung, Vince McMahon, the Governor of Kentucky all passed through to the expensive betting windows were they cut up, gambled and ordered drinks before returning to their luxurious balcony seats. Holding back my giddiness wasn’t too difficult because I was exhausted, until Kendra showed up.

I saw the big boobed bombshell making the walk from one of the Millionaires’ Row suites towards the balcony to my right. Her sleeveless pink dress showed off The Girl Next Door’s assets well, very well.   As she drew closer, I took a big gulp and just hoped she might say something. Then, she did.

“What’s going on in there?” she pointed towards the room, asking nobody, but I was there to respond. “A great time, if you’d like to see for yourself.” She laughed and my heart melted. She didn’t stop, but my heart did.

I just talked to Hef’s girlfriend! had to be all over my face. I don’t think I blushed in front of her, but my eyes were as wide as the hallway.  She continued on to the coveted balcony overlook of the paddock with a camera crew in tow. Even though that was nothing eventful enough to make it onto the reality show, my reality entered unforeseen territory. I may have encountered more famous people during the 30-minute period as a temporary protector of the Aristides Suite, but my memory is forever fogged with that unreal interaction.

Call to Post

Back on my patrol at the Matt Winn room, the day was flying by, to Will and I’s delight. Standing around with a smile on your face and schmoozing with rich folk is fine, but after so many hours all you can think about is loosening your tie and kicking your shoes off.

As I checked the program and the time, we were moving well ahead of schedule. “Hey Will, we could be getting out of here sooner than we thought,” I mentioned once, or twice, or ten times. Until I realized it wasn’t going to happen.

The penultimate race ended a few minutes before 5:00, giving the weary workers hope that the day would end early. My naïve brain didn’t realize that Derby wasn’t just like another normal race. Instead of the typical 40 minutes or so between races, there were almost two hours of waiting until the 6:38 post time. The additional time allows for more bets to be placed, more booze to be drank, and more Derby BSing.

After a deep sigh and a mope or two, I figuratively picked up my bootstraps and trudged along. I passed the time by giving out tips to anyone and everyone that would listen. My Derby horse was an easy choice — the 27-1 longshot, my horse of destiny, Denis of Cork.

The people who just wanted to win were rolling with the favorite, Big Brown. The women loved Eight Belles, the fist filly to run in nine years. The Santa Anita and Blue Grass winners, Pyro and Colonel John, were pretty popular, but whenever I asked who their horse was, Denis’ name never came up. I liked him because I met his owner, and you can’t hate on a gray horse with Calvin Borel on the mount near the rail at #3.

For the fancy rich folk, I was giving a hot take before they were called hot takes. They might have thought it to be a controversial pick, but I knew that something special was going to happen. After I told this tip to one of the Italians that snuck in guests right past me, he said he liked the tip so much he was gonna bet on it. I told him, “It’s a smart move,” while I thought, “You’re so full of it.” He returned ten minutes later with a $50 to win ticket for #3, “This one’s for you.”

I felt my face light up. The tip I had been waiting for finally came, only because I gave another tip. It was perplexing. I gave him a, “Thank you so much sir.” To which he responded with a cool, “I bet you’ll earn it.”

As grateful as I was, he couldn’t have put at least $5 on the horse to place? I don’t think I was being too conservative, I just wanted any amount of money I could possibly get my hands on. If this bet was going to be the only tip I got from the day, going all-or-nothing made me wish I had told him Big Brown was going to be the winner.

Time was ticking…closer…and closer. Fewer and fewer people were coming in and out of the room. Finally, the call to the post. I could hear it ring through the speakers but could only see the track if I backed into the dining room five yards or so in from the door and got onto my tiptoes. I was hesitant at first, but when “My Ole Kentucky Home,” I simply couldn’t stay away from the emotional Kentucky tradition.

The print of "My Ole Kentucky Home" that's featured in every Kentucky household.

The print of “My Ole Kentucky Home” that’s featured in every good Kentuckians household.

At this point I resigned to fulfilling the duties of my job. I had my eye on the door, but if somebody wanted to come in, I didn’t care. I was going to watch the Derby in person for the first time. To make things even better, I could see the entire track through the massive third floor glass windows. Before I knew it, the gate was filled and they were off.

It seemed a little surreal from behind the glass. There was a peculiar feeling inside; it was just too quiet. Watching with a wide view instead of the TV zoom was an unfamiliar sensation. The horses all moved in a massive group, with little differentiation between one or the other. The exception was the gray Corker near the bottom of the rail. As they neared the final turn, I was ready to say, “I TOLD YOU!”

Borel moved Denis of Cork to near the front and I could hardly contain my excitement. If he held on, I could double what I made in the three days with my Italian man’s one winning bet. “Holy shit,” I said under my breath, throwing my hands into the air, pausing midway through my exclamation to look around and make sure no one of authority saw me.

During that quick hesitation, Big Brown showed his stuff. I covered my mouth and the apathy set in. Big Brown won. Denis of Cork was third. If only he had given me that damn show bet.

During my first Derby I saw some things I will probably never see again.  I didn’t win, but I did figure out how to make the best out of a bad situation, my first step in “growing up.”

Instead of being stuck in my house or bitching about being on my feet all day, I learned about the track.  I met people that widened my narrow perspective on life.  I blushed.  I lost.

Most decisions you make as a teenager won’t affect you for the rest of your life, but trying to get beer on Spring Break did.  I worked for the attorney that helped me avoid serious legal trouble.  While working for the attorney, I thought I found my vocation, until I began listening to Kentucky Sports Radio while organizing the file room in the basement.  Now I’m telling you this story on Kentucky Sports Radio.

The story did not complete its full circle until I attended Derby for the first time as an adult.  I finally won received that coveted tip — $10 across the board on I’ll Have Another.

Article written by Nick Roush

"Look upon the doughnut, and not upon the hole." @RoushKSR

25 Comments for A 16-Year Old Security Guard For Celebrities: My First Derby

  1. Broski
    10:03 pm April 30, 2016 Permalink

    This is long

    • UK Big Board Update
      1:23 am May 1, 2016 Permalink

      I guess its safe to say you’ve never read a novel longer than The Cat in the Hat then, huh?

    • playmorezeppelin
      8:44 am May 1, 2016 Permalink

      Cat in the Hat: not a novel.

    • UK Big Board Update
      11:55 am May 1, 2016 Permalink

      To Broski, it is.

    • catsarerunnin
      1:01 pm May 6, 2017 Permalink

      Look what the Cats drug in….

    • Well, I see our resident self-appointed criticizer of the commenters who criticize a writer is back. It’s well known that net readers are typically non-linear readers.

      Big Board, you’re a pretty smart guy. Why do you contribute nothing but that? Hey, if someone criticizes a writer, they open themselves up. I get that. But you never contribute anything positive dude. Lighten up.

    • runningunnin.454
      1:14 pm May 6, 2017 Permalink

      Ha Ha; guys, this is a repeat from last year. I think Big Board has passed away.

    • Ouch. Oh well, I guess I have to start checking the dates. Embarrassed.

  2. Steady
    6:26 am May 1, 2016 Permalink

    You had me at Chelsea Clinton.

  3. Go Deep
    10:56 am May 1, 2016 Permalink

    I tried… Didn’t make it.

  4. BigBlue2U
    12:14 pm May 1, 2016 Permalink

    I kept waiting for a UK tie-in. We got Shagari Alleyne, and that was that. Probably a cool story for a 16 year old. Not a cool story for anyone out of high school.

    • Charleston Cat
      12:29 pm May 1, 2016 Permalink

      Why do you keep changing your screen name?

    • BigBlue2U
      8:41 am May 2, 2016 Permalink

      I’ve had this SN for well over a year, so I’m not sure what you’re referring to. But hey, keep up with you mediocre internet justice warrior skills, you’re doing great!

  5. ekywildcat
    12:54 pm May 1, 2016 Permalink

    Great story, but I don’t usually read story’s that long. A little warning next time, okay? Asshole.

  6. ronzo
    1:53 pm May 1, 2016 Permalink

    Why was Chelsea Clinton, who was 28 y/o in 2008, receiving Secret Service protection?

    • Nick Roush
      7:03 pm May 1, 2016 Permalink

      Hillary was running against Obama in the primary at the time.

    • catsarerunnin
      1:05 pm May 6, 2017 Permalink

      Yeah that was another election disaster for poor Hillary…

  7. Kat4Life
    2:17 pm May 1, 2016 Permalink

    I guess you had to be there………..

  8. The Original WTF Guy
    6:03 pm May 1, 2016 Permalink

    Another Nick Roush “Look At Me” post. Easily my least favorite writer here. Nick, when you’ve been to the Playboy Mansion like I have I’ll be impressed with your “saw Kendra at the Derby” story. Ah, probably not.

  9. runningunnin.454
    12:24 pm May 6, 2017 Permalink


  10. gobble gobble
    12:40 pm May 6, 2017 Permalink

    Nick, you’re the worst

  11. gobble gobble
    12:46 pm May 6, 2017 Permalink

    How can you be a journalism major and still be as bad as you are at writing?

  12. UKantPitino
    1:47 pm May 6, 2017 Permalink

    A good writer tells a story that takes you there, in your mind’s eye. You can picture the story as it’s unfolding and even feel some of the angst and joy the writer experienced, This was a good job Nick!

  13. RealCatsFan
    2:21 pm May 8, 2017 Permalink

    Biggest thing I remember from the Derby that year was the sad tragedy that unfolded with Eight Belles going down with two broken legs. Possibly the saddest moment in Kentucky Derby history. I can’t watch a horse race without thinking about it to this day. My wife and kids were in tears about it.