The Official Red Carpet Breakdown Of The Bet Gala: A Night Of Glitz, Glamour And Gambling Presented By Draftkings
Last night, the highly anticipated Barstool Sports Bet Gala took place in Scottsdale, Arizona. The DraftKings Sportsbook at TPC Scottsdale was alight with stars, the beating heart of the premiere Red Carpet event on the first Monday in May.
Fashionistas alike flocked to the live stream for the First Annual DraftKings Sportsbook Bet Gala Red Carpet, in the hopes of catching a glimpse of their favorite Barstool Sports Personalities. (Sadly, Miss Peaches had a prior engagement which comes as no surprise, amidst the news of her thriving new business, Lucky One Lemonade. Girl Boss!)
The Red Carpet Show opened with Barstool Royalty, hosts Francesca Mariano of Chicks in the Office, alongside Founder, Legend and Swiftie, Dave Portnoy.
Oops, sorry, here we go:
Francesca absolutely stunned in a Meshki strapless floor length floral gown, a nod to the tail end of an exciting Kentucky Derby weekend at Churchill Downs. A gorgeous rose in the winners circle, indeed!
Dave of course, having been the mastermind behind the event and Barstool’s first ever Lead Chairperson of the Bet Gala (Watch out, Anna!) left no stone unturned when it came to the finer things. His custom light blue suit is by noted designer Mr Formal, of Saratoga, NY. The navy accessories (how cute is that horseshoe detail on his tie?) accentuated the embroidered lucky pocket dice, as well as the very personal touch on the back of the blazer - an homage to Dave’s own Triple G, Go Go Greys stables - Twin Spires and all.
A quick mention of our Red Carpet boots on the ground, Nick Turani, who looked great while also having the tough task of intermediating between the bossman and the talent on the carpet. Lots of pressure not to totally blow it, and he navigated with ease. Except when Josh Richards didn’t know his name, that was embarrassing!
As for the Barstool Personalities, I think Francesca said it best:
“I have high expectations for some, and low expectations for others”
I will be judging all looks as I do every red carpet event, friends or not. Fashion is supposed to be exciting and creative and in an environment like Barstool Sports, monumental fashion moments are ripe for the taking. Let’s see what everyone has come up with.
Onto the DK-List stars….
Money Can’t Buy You Class
Dana Beers
Holy shit. My eyes!!!! I don’t know why I expected anything more from NYC’s one of Chicago’s resident Big Sweaty Drunk Idiots. Listen, I get the train of thought. Gambling….Money, Vegas, big chains around your neck and on your face (next time, pick one: neck or glasses. Not both.) If he were smart enough to realize those gold pants would photograph bronze, he would’ve been smart enough to come up with something more fashionable than this, so - I guess this is as good as it was going to get! All courtesy of Amazon, I’m sure.
Rico Bosco
Another money man with way too many cheap gimmicks. Those glasses….woof. Did he and Dana buy their looks together? Could they have gone to the nearest Party City in Scottsdale that morning? Who knows. So disappointing from my Dozen teammate Rico, though. He’s Mr Mafia and he forewent the opportunity to show up in a SHARP pinstripe suit + bowler with a cigar, for a bucket hat with 100 dollar bills on it? Sad. Only thing I’ll say in his favor - it fit him well, and no wrinkles I could see. He looked trim!
A For Effort, D For Dedication
Pat Bev
He not only looks good, but id put him on the best dressed list if he was even a LITTLE close to on theme. One single accessory or made up story about his look and he would’ve been up there. Great fit, fire all around, unfortunately a better fit for the MET Gala, themed “Tailored for you.” This is the BET gala, Pat!
Kayce, Elio and Megan
Elio did the money motif right with just one piece, a shirt, rounding out what seems to be a “Miami Vice” inspired look. I’m not sure how far in advance he knew about the Gala but, a Pink Blazer always makes me think of a quick back-of-the-closet-grab. He also wore a shirt with no collar while somehow still wearing a bowtie which, unfortunately, looked sloppy. Kayce and Megan flanking as his Monte Carlo casino gals is a great bit of theater but if not paired with Elio, we’re only looking at a couple of ladies heading to a fancy event. If the theme was “looking hot,” they’d be fine. Sadly, this is THE BET GALA!
Extremely Strange But Kind Of Fun
Jerry O’Connell and PFT
Jerry, I’m a huge fan. Truly love you and for that reason, I will say I enjoyed your time on this live stream. Your outfit? So, so hideous. You look like the Once-ler at the GLAAD awards. May God have mercy on us all. Your accents, vibes and hair, however? 10/10.
PFT in all snakeskin - what do you know? Do you have inside information about the impending release of Reputation (Taylor’s Version)? Why else would you be wearing snakeskin? Please report any and all information to Mad Dog at your earliest convenience.
The kidney stones on the carpet were APPALLING to me personally but also, kind of camp? Overall bone chilling experience from you both. Memorable to say the least.
Less Is More (But Sometimes, Not Enough)
Moobie & Kelly
Gorgeous. Both of these girls look stunning and, a little insider info, I know they’re coming straight off of a days long shoot in the desert. These girls took time out of their busy schedules to stunt on the hoes and stunt they did!! The money clutches are a perfect touch, especially as novice gamblers. Humble, classy, youthful. Love it ladies.
Bri and Josh
Another pair that would’ve crushed the theme if it were simply “being hot.” They both went simple, chic, cool. Zero attempt at the real theme from either of them but TikTok doesn’t care! They look like siblings more than ever and I’m sure BFF Dave is very thankful they made the trip. Josh had no issue making himself at home rooting for the Knicks with Meek Phill - someone do a wellness check on Tommy Smokes!
Steven Cheah
I love this look. Classic, handsome, great splashes of color - perfect for respecting the theme, looking sharp AND mixing in a little gimmick. He might’ve fallen into the boring category until I heard that his pops of purple were an ode to #TrustTheData, which happens to be the EXACT kind of self-promoting overthought I get down with.
Meek Phill
PHILLLL!!! Has anyone had more of a glow up lately? I bought stock early when he got this new haircut a while back, but I’d never expect him to be doing a personal rundown with Bossman the same day he’d serve face at the Bet Gala. The guy carries himself differently now and this red carpet is no exception. Not an ounce of theme on him but he gets some praise for looking sharp. Men need compliments too!!
Frank
Another guy cleaning up nice. I gasped when I saw Frank. Looking absolutely dapper as fuck. He even has a Mets bow tie!! If we want to get metaphorical about it, they always keep him in a chokehold! He even has Tank cufflinks. His tux is from NYC, and that’s something I love about Frank. He’s always going to rep his city! Nicely done.
Mark Titus
I mean, Mark looks nice. He’s got on a GREAT tux, he showed up, he went through some kind of trouble to get that ghastly foam horse hat - not my personal favorite accessory, but certainly not the worst. Unfortunately for him, there were better Horse-inspired looks, and better hats. Thank god for Pretty Privilege!
Best Use Of Accessories
Wallo & Gillie
Nice suits, big hats. That’s what these guys do. I have no notes. I’m sure they were the life of the party and apparently, they MAKE those big hats?? GOLDMINE! Basically zero effort into the theme if we’re being so real, but the DraftKings logo representation deserves some good points.
Somehow Worse Than The Dunkin Awards
Mintzy
What the fuck, actually. It’s borderline disrespectful for Mintzy to have put in this little of effort, and I don’t even dislike Mintz. His entire thing is gambling. It’s all he does. He should’ve dressed as the literal Draft King and instead we get some ill fitting funeral suit? Honestly, I don’t even want to shit talk the suit. It didn’t do anything wrong. Its wearer decided to dazzle us all and set our expectations even lower than they already are. Good god. And now we have THIS excuse?
Disgrace. Here’s the thing - fashion isn’t everyone’s forte! That’s why stylists exist!! You’d think Mintzy, or any of the others I’ve listed and will continue to list in this blog, would’ve asked any of the incredibly creative minds at Barstool Sports for a nod in the right direction if they were struggling, instead of resigning to “good enough”? Sorry, Mintz. Sashay away.
Thinking Out Loud, AND Of The Box
Hank
No shade, I actually hated this look. That’s not Hank’s fault, though - I HATE western wear. I’m going to Beyonce in a few weeks and I’m dreading wearing cowboy boots. But you know what? He took a fashion risk, and we applaud that. He had a reason for his look (even though it wasn’t on theme and seems as if he bought it all at one store in Arizona, possibly a boutique attached to the hotel), he took the time to put it together - this deserves a nod of approval. I’m not sure if the original gamblers were in fact, cowboys, but it sounds like a good story to me.
Big Ev
My guy. What a look!!! At first glance you think, ah yea, nice suit. Next thing you know, Ev’s showing us his CUSTOM jacket lining and then wait a second….props??? REAL BET SLIPS in his hand? Absolutely love it. Theatrics, focus, class. Great job Ev.
Jersey Jerry
JJ and I are not friends. At all. I’d go as far as to say I dislike him, and he knows it. That’s how you know it’s real (and painful) when I say - I loved his look. Absolutely crushed it. A sharp suit paired with clever and authentic accessories. Add in the element of comedy (being that Jerry could literally be a jockey) - it’s fantastic. As for his sketchy random ice cream friend? Bad outfit, but I’m intrigued by him. He’s bringing an element of mystery. HE makes me want to know what’s going on inside the DraftKings Bet Gala.
Brandon Walker
I don’t like to compliment Brandon Walker TOO MUCH (only because he barely compliments me anymore and that’s not an equal relationship) but he looked fabulous tonight. Good suit, good hair, looked like he belonged there. At first I thought he just wore a random nice blue suit he happened to have, until I learned…
Brilliant. Whether made up on the fly or planned in advance, this is the kind of thinking we need. Nicely done Brandon.
Klemmer
Let’s hear it for Klemmer! The only successful guy tonight to wear a full printed blazer, and actually look cool. Honoring the game of blackjack with an abstract deck of cards serving as the centerpiece to what I like to call, a home run.
The money people didn’t understand - it’s too obvious. It’s the #1 pick on Family Feud when you hear “gambling.” Overdone, overused, and often associated with “cheapness.” The more you flaunt it, the less you have. Cards show strategy, self control and luck, which is something I also thought of when I asked decided to appoint myself as a stylist and suggest a similar path for…
BEST DRESSED
John Feitelberg
Unfortunately I cannot put aside my bias on this one. John is my personal best dressed, not only because he looked fly as hell (flashing that Brick Watch? Lawd!) but because I offered to search for something fun he could wear and I found that shirt (which is BODE, by the way). I thought it’d be perfect for all of the reasons I love Klemmer’s look, but in a relaxed fit, quiet luxury way that’s more suited to Feitelberg’s style. John’s a true fashionista. We gossip over clothes on a weekly basis and I truly think it’s the cornerstone of our friendship. When he actually thought the shirt was cool, I had been secretly PRAYING it would be a hit so I could take credit, and boy was it:
“I liked Feitelberg, that shirt was cool.” - Dave Portnoy
Elated. Almost makes me forget all of the fomo I had not being invited. Thank you to John Feitelberg for being my first to semi-style for the Bet Gala.
Liam Blutman
On any other day, I look at Liam with concern. He’s a lovely guy, went out of his way once to help me turn some TVs on in the Chicago office, but I have a lot of questions about his heath and I don’t feel we are close enough that I can ask them. That being said, he tapped right into my style vein tonight. Absolutely mainlined. Fur coat? Rose colored glasses? Being a redhead with a blowout? You’ve found your target audience, Buddy!!! Mob Wife aesthetic. I can’t believe no one else thought of this. Now, I need to know - do we have a budding stylist on our hands? Liam says he dressed himself! He will certainly be one to watch.
Dan Katz
I am thrilled to see Chicago HQ Kingpin Dan “Big Cat” Katz leading by example with a fabulous custom number by none other than Mr Formal; on trend with his beloved boss and gambling counterpart, Dave Portnoy. “Dans guy” shows us more of his magic with custom pocket embroidery depicting Dan Katz’s iconic gambling run of 16-0, and an expertly stitched back panel cleverly reading “Overtaker”; the “O” adorned with what appears to be the actual DraftKings crown. What really pulls it together is the custom lining, complete with all of Dan’s winner future tickets. An inside source tells me his shoes and Spanx were both by Bet Gala carpet favorite, Amazon. Even the accessories - suspenders, money brooch, very well executed. The glazing is CRAAAAZYYY but this is how it’s done when you keep the lights on for everyone else. Effort in fashion shows you care! Bravo.
All in all, well done by the Gamblers of Barstool Sports. Most lived up to expectations, some fell flat, and Mintzy should lose future invites until he gets a stylist.
I’ve got to say, I’m disappointed to not see ONE photo of anyone smoking in the bathroom. These are the kinds of things that you miss when you don’t invite the real expert and DraftQUEEN, yours truly.
There’s always next year.
