Ugly Hooker Approaches Working Class Man In Las Vegas, All Hell Breaks Loose

Not even the purest of souls can outrun the Devil in Las Vegas.

As OutKick readers know, I go to Las Vegas yearly with a large group of fellow veteran Sin City operators, and every trip brings us new adventures, challenges, stories, demons to hunt and memories we cherish and try to forget in our darkest hours.

The highest of highs. The lowest of lows.

This is the story of the 2025 trip. As always, names have been withheld to protect national security and the identities of those involved. The rest is a true story - even if we wish it wouldn't be.

Las Vegas didn't disappoint at all this year, but it wasn't what we were expecting. The demons come to play at night. (Credit: David Hookstead)

Las Vegas 2025 was one for the books.

To tell this story, we actually have to start a couple of days before I arrived in Sin City. The date was August 8, and I was boarding a plane not bound for Las Vegas.

The destination was Chicago. The goal? A wedding featuring enough tennis players to fill a tournament. My fiancée's former teammate was getting married, and for the first time in at least 15+ years, I found myself in Chicago.

As a Midwest man - born and raised in the harshest winters Wisconsin has to offer - I've always been fond of Chicago. However, I truly don't even know what the city is like in 2025. Last time I was there was for a Lions/Bears game back before Matthew Stafford was slinging it for Detroit.

Was it going to be another urban hellhole like Washington, D.C. has become or did it still have its spirit? The answer, fortunately, was the latter.

The food scene in Chicago was outstanding, and the wedding was full of some really cool people with some fascinating stories to share.

I was also hooked up with a nice place to stay through a [redacted] connection. When I say nice, I mean the *HEIGHT* of luxury. Guys like me are generally shot on site if we try to enter nice places. It's almost like they can smell my blue-collar roots, and want nothing to do with it. Luckily, I blended in enough that I don't think the location we were staying knew my true identity. I did get told one time to take my hat off, but the guy was super polite about it. No harm, no foul.

Following the wedding, I had the gift of a 4 a.m. hike to the airport. This was my first real test in Chicago. The streets might be fine in broad daylight. Darkness is a different kind of beast, and to the surprise of nobody, the human zombies were out before the sun was up. Fortunately, I'm not the tiniest guy on the planet, and I made it to the airport without any issues. That's a good update because I've got enough cash on me to buy a car, and the last thing I want to do is have to punch holes in someone thinking about doing something very stupid.

I am beyond exhausted at this point. I got a couple hours of sleep, I'm struggling to keep my eyes open after multiple caffeine drinks and I feel like I'm going to crash. As soon as I sit down in my seat on the plane, I take out my pillow and go to sleep, assuming I'll wake up somewhere over the Rocky Mountains.

Wrong.

I wake up roughly an hour and a half later, and the plane is still at the gate. I'm beyond confused, but there was apparently some kind of issue delaying take-off. Welp, there is 90 minutes of wasted time, but at least I got some rest.

After another energy drink, I'm finally rolling, crushing through some TV shows. The plane touches down and I'm off to link up with a couple buddies who landed around the same time.

Unfortunately, our Vegas trip has multiple major issues before it even gets started. Those being the temporary closure of three places we love hanging out at:

• Stage Door
• Hogs & Heifers
• Battlefield Las Vegas

All three are closed for different reasons, and all three should be back up and running by the next time I'm in town. For now, we have to immediately pivot. As the saying goes, no plan survives first contact with the enemy. Not to worry, we always have backup plans and our backup plans have backup plans.

First visit is a bar near The Linq to get some food and drinks. You can fight your way to success in Las Vegas. After grabbing some food and our first Las Vegas beers, I'm ready to roll. The rest of the crew needs to acquire some goods, and while they're doing that, I'm headed straight to Cosmo to play high-limit blackjack. I have a pocket full of money and dreams of success.

My very first beer in Las Vegas. I can promise it wasn't the last one. (Credit: David Hookstead)

Little do I know a nightmare is waiting for me.

For those of you who have never been, Cosmo is an incredibly nice Las Vegas hotel. It's marketed to an upper-class crowd that is relatively young. I love walking through there, and I can't wait to get to the high-limit room to start playing blackjack. It's a massacre.

I lose a paycheck in the span of about 10 minutes. I'm out several thousand dollars in the blink of an eye. You have to know when to walk away. The cards aren't in my favor right now. I push back from the table, and decide to hit up Ellis Island with my buddies.

For those of you who don't know, Ellis Island is a massive hidden gem in Las Vegas. It has some of the best gambling options, incredible food and drinks and is just a block off the strip. It's one of my favorite places.

Unfortunately for me, the nightmare is just getting started. I lose another $300 without even having time to think about it. I've never been on a bad blackjack run like this in my life.

I need to do something and do something fast to turn the tide. 

We're about to experience a run unlike anything I've done before.

I headed to Virgin Casino - a place I've never played before. Again, it's straight to the high-limit room, and I don't know it yet, but this whole trip is about to change.

I put a few hundred dollars on the table with a broken spirit and a broken soul. I start pulling cards that I couldn't replicate again if my life depended on it, and the cocktail waitress makes sure the Coors Lights arrive as soon as I'm finished with the current one. That's the beauty of high-limit rooms. The customer service is incredible, but nobody is focused on the cocktail waitress.

I'm the only person in the entire high-limit salon, and I have the casino's attention. The reason? I turned a few hundred dollars into WAY MORE before anyone knew what had happened. The pit boss, other dealers, cocktail waitresses and anyone with a pulse is locked in. I simply can't lose, and no, I'm not counting cards. I'm simply playing perfect basic strategy (minus one mistake that briefly cost me dearly).

I have more money on the table than I've ever personally had before. The chips simply do not stop stacking up. Just like walking away when losing, you have to know when to walk away when winning.

I tip out the dealers, finish my drink and head to the cage. There's a series of communications that happen between the cage and what seems like several people. I'm asked a handful of questions about what happened and where I got the chips. Once my story is verified as real, I'm paid out immediately.

A look at $1,000 chips from Virgin. (Credit: David Hookstead)

What do you do after the wildest gambling run of your life? You celebrate, and that's what we did with a quick dinner and a couple Coors Banquets.

It's now fairly late at night, and people are splitting off to head to bed. I decide to walk the strip, and head over to Wynn. This is where this story is going to take a wild turn that I've never experienced before.

Keep in mind that I'm a regular dude, and I look like a regular Midwestern guy. I don't like people approaching me, and I never speak to people I don't know in public. I consider it extremely taboo.

You know who doesn't? Hookers.

About 30 seconds after Wynn, the ugliest hooker imaginable approaches me, and asks me if I "want to party" with her. For those of you who don't deal with these morons, that's code for asking if I want to have sex with her.

One, I'm engaged, and maybe even more importantly, I wouldn't touch any hooker with a 15-foot pole. This one is a special breed of disgusting. She's white, maybe 5'7", overweight and covered in gross tattoos. It's like looking at a walking petri dish.

I'm not even sure why, but I'm enraged this woman spoke to me. I don't show it, but I'm through the roof. In what world would this woman think it's acceptable to walk up to me - a working class American - and proposition me? This lady could have been the last woman on the planet, and I still wouldn't have touched her.

Now, due to OutKick being a family-friendly website, I won't publicly share what my response was. Use your imagination, and then 10x it. I was in no mood for her BS. I don't like talking to people I don't know, and I absolutely hate people I don't know speaking to me. It's been that way my entire life, and it's only getting worse as I get older.

Now that I dispatched the nasty hooker, I decided to hit up Gilley's for a little country music and a nightcap Coors Banquet. It was a fairly nice experience. I'm a sucker for live music, and it doesn't disappoint. The band crushed it.

At this point, I'm once again exhausted, and it's time for me to head to bed. I shut my eyes tired, but eager for what comes next.

A view of The Strip from an overpass on my first night in Las Vegas. (Credit: David Hookstead)

Day two - Backup arrives.

Most of the crew arrived on Sunday, but two of our most seasoned Las Vegas operators arrived Monday afternoon. These two are critical members of the Las Vegas crew. They're not just great teammates, but both are more than capable of operating independently in the city. This is an invaluable skillset, and it's needed.

Both arrive in Vegas, and at this point, we're locked, loaded and ready to crush anything in front of us. While waiting for them, I decide to head back to Cosmo's high-limit room and see if I can avenge the bloodbath from day one.

It essentially turns into a draw. I come out a little head, but I'm still down huge overall at Cosmo. That's okay. It's a long trip, and while Cosmo might have drawn a lot of blood early, I'm confident I'll be able to get it back - even if I have to simply chip away at doing it. Remember, it's not a real loss until you leave Las Vegas. It only ends once. Everything else is just progress and part of the story.

I hit up Ellis Island for a burger and fries that *ALL IN* with tax and tip was about $10. It was shockingly cheap and incredibly tasty. Finding a deal like that in Las Vegas is about as rare as a unicorn sighting, but that's why we go to Ellis Island.

A look at my cheap burger and fries at Ellis Island. (Credit: David Hookstead)

Eventually, the decision is made to head to El Cortez in Fremont. Usually, this is when we'd head to Hogs & Heifers, but again, it's temporarily closed. A big loss that we're all feeling, but it will return to fight another day.

What I didn't expect was what I walked into at El Cortez. There's been a lot of remodeling, and personally, I'm not a fan of what I find.

The biggest appeal of El Cortez is that it feels like stepping into a time machine. There's a lingering of cigarette smoke, there are plenty of beers flowing and the blackjack tables have great odds. While some of that remains true, the entire vibe felt off. It didn't feel like the walls could talk and tell crazy stories of the old days.

It felt like…….a modern casino. That's not what El Cortez is supposed to be about. In fact, it's the exact opposite of what El Cortez is all about. Not a fan. Not a fan at all, but we do hit up the tables for a little bit without any significant swings worth mentioning.

Overall, an incrediby disappointing time at El Cortez, and this is the only time I've ever felt that way. I will definitely return to give it another shot, but for now, I fear it's been lost to its upgrades. I hope the vibes were just off that one time, and it's not the new normal.

With gambling for the day behind us, we decide to try our hand at axe throwing at Axehole. I've never been axe throwing before. I'm not bad with a firearm (more on that soon), but axe throwing is a totally different beast.

I'm not just bad. I'm absolutely terrible. If the zombie apocalypse happens, and all I have is an axe, then I'm probably cooked.

Yet, it was a shocking amount of fun, and we got a throwing lane for an entire hour at a very reasonable price.

The staff was exceptional, the beer was decently priced and having a couple beers while trying to demolish things with multiple different weapons is incredibly fun.

I naturally had to wear my "Red Dawn" shirt while throwing axes. (Credit: David Hookstead)

Overall, a great way to end day two, and something I'd probably do again down the road. Now, time to count my money, lock it in the safe and get some rest.

Day three - get ready to sling some lead.

Before the sun is even up all the way, I find myself back inside Cosmo's high-limit room trying to claw back some of my losses. It's not going well, but I'm not dead just yet. It feels like every punch the cards throw, I'm able to counter. All in, I do lose a little but not enough to worry about.

There's something I'm desperate to try:

Craps.

I've never really played craps before, and I'll be the first to admit that I don't know much about it. However, I'm desperate to learn because a hot craps table always looks like a blast.

A buddy of mine - one of the more seasoned guys - and I locked into a craps table at Ellis Island, and the incredible dealers were very patient and eager to help us learn.

Next thing I know, we're not just winning, but winning in a big way. It's exhilarating. I never knew how fast you can stack money in craps or lose it all in the blink of an eye.

It doesn't take long to understand why people are obsessed with this game. I walk away with a nice little sum of money, and it's now time to do something I love in life:

Shoot weapons.

Normally, we'd be at Battlefield Vegas, but it's temporarily closed. Fortunately, one of the guys with us has a connection to someone at The Range 702, and we decide to give it a shot.

It didn't disappoint. I shot several fully automatic weapons, including a SAW. It was an absolute blast. Our range safety officer, Maddie, was a rock star.

You can watch some of the footage here, and check out one of the targets I tore up with an MP5. Threw a couple shots on fully auto, and while I'm not as sharp as I was as a kid, I guess I'm still alright on the trigger.

Definitely check it out if you're in Las Vegas. You won't regret it. Great location with incredibly professional staff and a nice arsenal of weapons.

The boys at the gun range. Identities hidden to protect them. Our range safety officer is next to me, and was awesome at her job. (Credit: David Hookstead)

A look at the SAW. It's a ton of fun to shoot. (Credit: David Hookstead)

After tearing it up at the gun range, we decide to hit a variety of different places for drinks. Specifically, we check out Able Baker Brewery, Stray Pirate and Dark Sisters.

All three are great, but Stray Pirate is next level cool. Tiki bars, by default, are cool. Stray Pirate took things to an entirely different level.

The drinks were all incredible, the vibes were off the charts, and the entire place was loaded with cool photos and decorations.

There was also a very heavy pro-dog vibe, which I appreciated. We also found ourselves doing what guys always do when they get together:

Talk about WWII for hours on end.

Wouldn't have it any other way.

A painting inside Stray Pirate. (Credit: David Hookstead)

A look at the Goonies Never Die at Stray Pirate. (Credit: David Hookstead)

To close out the day, we decided to hit up the High Roller. It's a giant ferris wheel with pods that take you up high into the sky to get a view of Sin City.

I've never done it during the day. I can't imagine it's very fun during the day, but it's epic at night. The view is nothing short of incredible.

Unfortunately, we had to deal with some absolute dumbasses who were in our pod. A bunch of French idiots wouldn't shut the hell up or behave in a civilized manner.

I can't tell you all how much I hated one of these guys. Loud, dirty, obnoxious, an annoying accent and behavior I wouldn't tolerate out of a small child.

I guess he must have forgotten about D-Day and WWII. The only words I ever want to hear from any French person are "thank you" after we liberated them and saved their country during WWII.

These bozos made the entire country look like it's full of the worst people on the planet. Don't come to my country and behave with anything less than total and complete respect - just like I would in yours. Things nearly got a bit too spicy up in the air, but fortunately, nothing crazy had to happen.

The view from the High Roller is amazing....even if you do have to deal with French people. (Credit: David Hookstead)

We ended the night at a nearby bar and shut it down, sharing stories. Back to bed to rest for our final full day in Sin City.

Day four - a near disaster.

Day four started just like many days in Las Vegas have. With breakfast and gambling (specifically biscuits and gravy).

Biscuits and gravy is the perfect breakfast food. (Credit: David Hookstead)

Remember previously in this article when I spoke about winning at craps and how it can all happen in a flash? Well, get ready for the inverse of that event.

I returned to the craps table assuming I'd find the same luck and success.

I did not.

I lost most of my bankroll in a matter of minutes. What Vegas gives, it can absolutely take back. That's what happened. You can get bummed about it, or simply realize it's the cost of business in this dirty game we call visiting Las Vegas.

After deciding I was done losing money for the time being, I had a couple great cocktails at The Front Yard, and then hit up something I wouldn't ever expect to do in Las Vegas.

Mini-golf at the Horseshoe.

It was shockingly fun. I probably last played mini-golf at some point in middle school. Maybe earlier. It sounds a bit odd for a bunch of grown men to do, but everyone was in agreement that it was a great experience.

The signs on the wall were also exceptional.

The Horseshoe in Las Vegas has some shockingly fun mini-golf. (Credit: David Hookstead)

With mini-golf behind us, the boys had one goal and one goal only in mind:

Hit up the Golden Tiki ASAP.

The Golden Tiki is a legendary spot in Las Vegas with some of the best drinks and decor on the planet. It's a blast, and the staff is also great at making sure everyone has a blast.

After a handful of tiki bar drinks, we decide to venture into uncharted territory. The bartender at our lunch spot recommended checking out a place called Sand Dollar. She said it's her favorite place in Vegas.

A quick look at her told me she likes to party. That's credible enough for me. We hit up Sand Dollar, and it was an outstanding dive bar with cheap drinks, epic music, tasty pizza and pool tables.

Both sets of my grandparents have pool tables in their homes, but I haven't played in at least 20 years. Yet, after a friendly challenge, I find myself in an epic battle on the pool table. I won only one of three games, but it was a lot of fun to get back into the action.

We then drank a couple beers (and an espresso martini!) and discussed every topic under the sun for hours and hours. Before I knew it, it was about 11:00 p.m., and with everyone leaving in the morning, we decided to head back and call it a trip.

Who knew I was an espresso martini man? (Credit: David Hookstead)

I hop up on Thursday without having gone broke, didn't get touched by a nasty hooker, went on the most epic gambling run of my life and had too much to explain while doing it. I even got to trash the dirty French. What more could you ever want? Was it the most insane Vegas trip ever? No, but it was a great new installment into a saga that's been going on for years. Now, we rest, lick our wounds and prepare to get back on the ground in a year. Do you have a fun Vegas story? Let me know at David.Hookstead@outkick.com.