Billy Football Breaks His Silence on Future at Barstool (And Africa) | Drop A Pin Ep. 19

This week on Drop A Pin, Donnie and Chaps are joined by Barstool founder and El Presidente himself, Dave Portnoy, for a deep dive into one of his favorite places on Earth: Nantucket. 🔑 In this episode: 🏠 Why Dave Loves Nantucket: Portnoy shares how he first discovered the island 💸Dave talks about the current state of Nantucket’s insane real estate market ⚓ The Island’s History: Donnie breaks down how Nantucket went from being the whaling capital of the world in the 1800s to a high-end getaway destination. 🍽️ Scalloping on His Property: Dave explains how he found himself with active scalloping rights on the lot he bought—and what that actually means in terms of local rules and seasonal seafood. 🍕 Pizza Reviews in Saudi Arabia: Dave may be doing a pizza fest in the Middle East 💅 Getting Cultured with Annika: In our recurring segment, Barstool's Annika asks talk about getting some work done abroad Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping. https://BlueChew.com GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 5/18/25 at 11:59 PM ET. Sponsored by DK. Get $10 Off @BRUNT with code DROPAPIN at https://bruntworkwear.com/DROPAPIN! #bruntpod Head to https://Ollie.com/DROPAPIN and use code DROPAPIN to get 60% off your Welcome Kit when you subscribe today! Go to https://www.heydude.com today and find your perfect pair 🎧 Drop A Pin is live now on YouTube, Spotify, and Apple Podcasts. 📍#DropAPin #BarstoolSports #Nantucket #OneBite #SaudiPizza #ElPresidente #BarstoolTravel #ScallopingSeason Follow The Wonton Don! IG: thewontondon TikTok: thewontondon twitter: @donniedoesworld FB: / donniedoes Barstool: https://www.barstoolsports.com/bio/62...

🎙️ Drop A Pin: Frank “The Tank” Fleming’s Producer, Matthew Piper Jenks Takes Flight + Embracing the Florentine Spirit ✈️🇮🇹 🚨 This week’s episode is a must-listen for travel enthusiasts and Italy aficionados! @DonnieDoesWorld & @UncleChaps welcome the one and only Matthew Piper Jenks—producer to Frank “The Tank” Fleming—who shares his incredible experiences living in Florence. From intense Calcio Storico matches to the captivating Palio di Siena, Jenks and Donnie swap stories of adrenaline-fueled spectacle and genuine cultural immersion. You’ll hear how one warm-hearted Florentine family welcomed Jenks like their own son, creating memories he’ll never forget. Timestamps: Interview With Jenks - 00:00:44 Florence Discussion - 1:33:16 Gettin' Cultured with Mark Titus - 2:12:42 🎤 Matthew Piper Jenks: The Man Behind the Legend of Frank The Tank & His Life in Florence 🔹 Calcio Storico: Jenks and Donnie break down the historic—and sometimes downright brutal—sporting event and why it’s a must-see for anyone visiting Florence. ⚽ 🔹 Palio di Siena: Hear about the centuries-old horse race that captivates an entire city, and learn what makes this tradition a true bucket-list experience. 🏇 🔹 Florence Family Ties: Jenks reveals a heartfelt story of how a local Florentine family embraced him, giving a fresh perspective on Italian hospitality. ❤️ 🎙️ THEN… Mark Titus Joins for “Gettin' Cultured” for advice on Fatherhood & Travel ✈️👨‍👧 Mark Titus slides into the airplane seat for a candid chat about his upcoming journey into fatherhood and his burning desire to keep traveling. 🔹 Parenting on the Road: How to prepare for family trips without losing your mind—or your passport. 🍼🌍 🔹 Advice from a Veteran Father: As a seasoned father Chaps share his top tips and travel hacks for traveling with a child. 🔥 This episode has it all—Italian sports, heartfelt stories, culture-shock anecdotes, and fresh perspectives on balancing fatherhood with a passion for travel. 💬 Let us know—what’s your favorite Italian tradition or destination? Share in the comments below! Download the Gametime app today and use code DROP for $20 off your first purchase GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 5/18/25 at 11:59 PM ET. Sponsored by DK. Control Body Odor ANYWHERE with @shop.mando and get $5 off off your Starter Pack (that’s over 40% off) with promo code WONTON at https://shopmando.com! #mandopod Go to https://www.heydude.com today and find your perfect pair Download the Gametime app today and use code DROP for $20 off your first purchase GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 5/18/25 at 11:59 PM ET. Sponsored by DK. Control Body Odor ANYWHERE with @shop.mando and get $5 off off your Starter Pack (that’s over 40% off) with promo code WONTON at https://shopmando.com! #mandopod Go to https://www.heydude.com today and find your perfect pair 🎧 Listen Now: 📍 Apple Podcasts | Spotify | YouTube 📲 Follow & Subscribe: @BarstoolSports | @TheDropAPinPod Follow The Wonton Don! IG: thewontondon TikTok: thewontondon twitter: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Barstool: https://www.barstoolsports.com/bio/62720/donnie-does Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps Twitter: @UncleChaps Barstool: https://www.barstoolsports.com/bio/13906103/chaps

🚨 This week’s episode is an absolute can’t-miss for all you travel junkies! @DonnieDoesWorld & @UncleChaps dive into their unforgettable adventures in Thailand—from Donnie’s early content creation days to the wild stories to crazy festival experiences Donnie & Chaps: Life & Laughs in Thailand • From the Streets of Bangkok to the Islands: Hear about the nightlife, hidden gems, and local delicacies that left Donnie & Chaps wanting more! 🌃🌴 • Donnie’s First-Ever Content Series: Get the backstory on how Donnie took the leap into vlogging, the challenges he faced, and how Thailand played a massive role in his journey. 🎬💥 • Tyler, a new Barstool producer, reveals how he got busted smoking weed in Thailand—and the hectic bribe he had to pay to dodge trouble with the cops. 🚨💰 • Lessons Learned: From facing local laws head-on to making it out unscathed, Tyler shares the adrenaline-packed story and how it changed his perspective on traveling. 😬🌏 Gettin’ Cultured with Steven Cheah • Why Do Different Countries Drive on Different Sides of the Road?: Steven stops by to break down the fascinating history, cultural quirks, and sometimes dangerous realities behind left-side vs. right-side driving. 🚦🤔 • Travel Adjustments & Tips: Whether you’re a first-timer or seasoned globetrotter, learn how to adapt when hitting the roads in countries with traffic flowing in “the other lane.” 🛣️✅ 🔥 This episode is loaded with Thai memories, production secrets, and global insights. It’s a must-watch for anyone craving a little wanderlust! Let us know—what’s your top tip for staying out of trouble abroad? Drop it in the comments! Listen Now: 📍 Apple Podcasts | Spotify | YouTube Follow & Subscribe: @BarstoolSports | @TheDropAPinShow #DropAPin #ThailandTravel #PeakinSeries #DonnieDoes #UncleChaps #StevenCheah #BarstoolSports #DrivingAbroad #CultureShock Follow The Wonton Don! IG: thewontondon TikTok: thewontondon twitter: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Barstool: https://www.barstoolsports.com/bio/62720/donnie-does

This week’s episode of Drop A Pin is loaded with wild travel stories and big laughs! @DonnieDoesWorld & @UncleChaps bring you the legendary Sam—the dedicated Barstool fan who joined Donnie on his now-infamous #Baldstool adventure. Buckle up for on-set plane seat antics, epic tales from India, and a touch of global intrigue. 🪑✈️ Timestamps: 00:53 Interview with Sam 2:04:04 Gettin' Cultured with Big T 🎤 Sam’s Wild Ride: From Baldstool to India 🔹 Baldstool Beginnings: Hear how Sam ended up shaving it all and following Donnie on an around-the-world escapade—truly a life-changing leap. 🔹 Highs in India: From navigating bustling streets to witnessing iconic landmarks, Sam and Donnie share their most memorable moments on the subcontinent. 🌏 🔹 Hezbollah Encounters in Lebanon: Get the inside scoop on Sam’s unexpected run-ins with Hezbollah—an adventure straight out of a spy thriller. 🤯 🎙️ THEN… Big T Takes the Mic on Being a LARGE Traveler 🏋️‍♂️💺 @BarstoolBigT joins to chat about the ups and downs of globe-trotting when you’re bigger than most airplane seats. 🔹 Cramped Airline Struggles: Which carriers get a thumbs-up, and which leave you with bruised elbows? ✈️ 🔹 Fit to Travel: How Big T handles seatbelt extenders, tight hotel rooms, and travel hacks every large traveler needs in their back pocket. 🤯 🔹 Surprisingly Comfy Destinations: Discover the places that truly welcomed a 6’5”+, 300-pound traveler—and the ones that definitely did not. 🏨 🔹 Sharing the Journey: Donnie, Chaps, and Big T compare stories of destinations that blew their minds, proving you never know what you’ll love until you explore. 🌐🔥 🔥 This episode offers comedy, culture, and a real look into how travel can surprise you around every corner (sometimes involving unexpected groups like Hezbollah). 💬 Tell us—what’s the most unexpected place you’ve found yourself while traveling? Drop your stories in the comments! Download the Gametime app today and use code DROP for $20 off your first purchase Go to https://www.heydude.com today and find your perfect pair Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV). Help is available for problem gambling, call (888) 789-7777 or visit ccpg.org (CT). 21+. Physically present in CT/MI/NJ/PA/WV only. Void in ONT. Eligibility restrictions apply. 1 per new customer. Opt-in req. Min. net loss of $5 on eligible games to earn 100% of net losses back (“Lossback”) for 24 hours following opt-in. Max. $1,000 issued in Casino Credits for select games that are non-withdrawable, single-use, have no cash value, and expire in 7 days (168 hours). Terms: casino.draftkings.com/promos. Ends 4/27/25 at 11:59 PM ET. Sponsored by DK. 🎧 Listen Now: 📍 Apple Podcasts | Spotify | YouTube 📲 Follow & Subscribe: @BarstoolSports | @DropAPinPod #DropAPin #Baldstool #IndiaTrip #Hezbollah #Lebanon #BarstoolSports #SamTakesOnTheWorld #BigT #TravelPodcast #ComedyTravel #DonnieDoes #UncleChaps #Adventure #MustListen #GlobalAdventures Follow The Wonton Don! IG: thewontondon TikTok: thewontondon twitter: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Barstool: https://www.barstoolsports.com/bio/62720/donnie-does Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps Twitter: @UncleChaps Barstool: https://www.barstoolsports.com/bio/unclechaps

In this episode of Drop A Pin, Donnie Does and Uncle Chaps are joined by comedian, world traveler, and globetrotting storyteller Giulio Gallarotti (@notjulio) to talk about the wild trip: vacationing in Iraq and Afghanistan. Yes, you read that right. Chaps reflects on his time in Iraq through the lens of combat as a Marine, while Donnie and Giulio hilariously recount their civilian travels to the very same regions—not as soldiers, but as tourists. From ancient ruins to modern-day chaos, they compare what it's like to visit these countries with wildly different perspectives. 🌍✈️💥 Topics include: Giulio’s bold decision to vacation in Afghanistan 🇦🇫 Touring Baghdad vs. surviving Fallujah 🇮🇶 How travel changes your worldview—even in warzones Cultural gems, local hospitality, and surreal moments in conflict regions Comedy, courage, and how far curiosity will take you If you’ve ever wondered what it’s like to visit places most people only see in headlines, this episode will open your eyes—and probably make you laugh. It’s a wild, thoughtful, and unexpectedly inspiring ride. 🔔 Don’t forget to like, comment, and subscribe for more insane travel stories and global weirdness every week! #DropAPin #GiulioGallarotti #TravelPodcast #IraqTravel #AfghanistanTrip #DonnieDoes #UncleChaps #CombatVsVacation #WarzoneTourism #MilitaryVsCivilian #TravelComedy #WorldExplorer #CrazyTravelStories #ChapsInIraq #GiulioInAfghanistan #GlobalAdventures 📍 Watch now on YouTube + Listen wherever you get your podcasts! Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping. https://BlueChew.com Go to https://www.heydude.com today and find your perfect pair Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV). Help is available for problem gambling, call (888) 789-7777 or visit ccpg.org (CT). 21+. Physically present in CT/MI/NJ/PA/WV only. Void in ONT. Eligibility restrictions apply. 1 per new customer. Opt-in req. Min. net loss of $5 on eligible games to earn 100% of net losses back (“Lossback”) for 24 hours following opt-in. Max. $1,000 issued in Casino Credits for select games that are non-withdrawable, single-use, have no cash value, and expire in 7 days (168 hours). Terms: casino.draftkings.com/promos. Ends 4/27/25 at 11:59 PM ET. Sponsored by DK.

🌎 Ari Shaffir Joins Donnie & Chaps for a No-Frills Travel Deep Dive ✈️ Hostel Life: Ari shares unfiltered stories from dirt-cheap stays, including bunking with strangers, wild hostel parties, and unexpected friendships. 💸 Budget Travel Hacks: How Ari stretches a dollar on the road—sleeping in airports, hitchhiking, and eating like a local. 🏝️ Off-the-Grid Adventures: From hidden villages to under-the-radar countries, Ari talks about the best (and worst) places he's wandered into. 🤢 Sketchy Situations: A few close calls—dodging scams, weird food experiences, and the occasional "should I be here?" moments. 📚 Gettin’ Cultured w/ Nick Turani 🤔 Chaps & Donnie challenge Nick with travel trivia and odd cultural facts. 🏆 Can Nick guess the customs, taboos, or weird laws from different countries? 😂 As always, chaos ensues.

Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping. https://BlueChew.com Go to https://www.heydude.com today and find your perfect pair, the official comfort shoe of Barstool sports Drop A Pin is sponsored by BetterHelp. Visit https://BetterHelp.com/WONTON today to get 10% off your first month. In this electrifying episode of Drop A Pin, Donnie Does and Uncle Chaps sit down with LOCASH, the country music duo behind hit songs like I Love This Life and One Big Country Song! From sold-out shows to terrifying moments in the sky, this episode is packed with wild tour stories, industry secrets, and some close calls. What’s Inside This Episode? 🎤 The LOCASH Journey – How they went from songwriters to country music stars, writing hits for legends like Keith Urban & Tim McGraw. 🚛 Life on the Road – The highs and lows of touring across America, performing for thousands, and chasing the next big hit. 🏆 Chart-Topping Success – The grind behind making music that climbs the country charts and lands on playlists everywhere. ✈️ Near-Disasters in the Sky – The guys share wild plane stories that will have you double-checking your seatbelt the next time you fly! 🤣 Hannah Montoya Gets Cultured – Stuck in the dreaded middle seat, Hannah joins for another round of travel talk and culture questions with Donnie & Chaps. 🔥 This episode is a must-listen for country music fans, road warriors, and anyone who loves a crazy tour story! 📲 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts! #DropAPin #LOCASH #CountryMusic 🎸 #TourLife 🚛 #OneBigCountrySong 🎶 #MusicIndustry #TravelStories ✈️ #PlaneDisasters #GettingCultured #BarstoolSports 🎤 #HannahMontoya #DonnieDoes #UncleChaps

Wall Street’s Wild Days with Large 💰 This week on Drop A Pin, we’re heading to the heart of American finance—Wall Street. And who better to guide us through the highs, lows, and absolute insanity of the late ‘90s and early 2000s than Barstool’s very own @LargeBarstool? 🔹 History, Lore, and Scandals Large shares firsthand stories from his time as a trader, painting a picture of a financial world fueled by high stakes, even higher egos, and legendary blow-ups. From the dot-com bubble to Enron’s implosion, the guys break down some of Wall Street’s most infamous moments. 🔹 The Wild Side of Wall Street It wasn’t all about stocks and IPOs—Wall Street had its own culture of excess. Large pulls back the curtain on six-figure steak dinners, legendary cigar lounges, and martini-soaked afternoons that defined the era. Ever wonder where Gordon Gekko types actually hung out? This episode has you covered. 🔹 The Food Scene of Finance Bros From old-school chophouses to legendary delis where deals were inked on the back of napkins, we explore the culinary institutions that fueled the bulls and bears of New York City. Plus, Large reveals his go-to power lunch spots that are still standing today. 🏛️💸 From the greed-fueled ‘90s to the Great Recession’s fallout, this episode is a deep dive into Wall Street’s most notorious era—through the eyes of someone who lived it. 🎙️ Getting Cultured To close things out, @DonnieDoesWorld and @UncleChaps bring back Getting Cultured, answering travel questions and diving into some of the more questionable financial customs around the world. Drop A Pin is sponsored by BetterHelp. Visit https://BetterHelp.com/WONTON today to get 10% off your first month. 👉 Listen now wherever you get your podcasts! #DropAPin #WallStreet #FinanceBros #BarstoolSports #History #WallStreetScandals #TradingFloor #NYCFood #WallStreetLore #LargeBarstool

🎙️ Drop A Pin: Sam Tallent Takes Flight + Traveling as a BIG, BIG Man ✈️🌍 🚨 This week’s episode is a must-listen for comedy and travel lovers! @DonnieDoesWorld & @UncleChaps welcome the hilarious Sam Tallent (SamTallent) into the studio, where he becomes the first-ever guest to sit in our studio plane seats! 🪑✈️ 🎤 Sam Tallent: The Comedian Who’s Been Everywhere 🔹 The Art of Small-Town Comedy: Sam shares wild stories from performing in tiny venues across America, where the crowds are rowdy, unpredictable, and sometimes too involved. 🎭🏚️ 🔹 Lessons from the Road: From grinding through dive bars to playing real comedy clubs, Sam dives into what it takes to make it in stand-up. 🔹 Performing Around the World: Comedy isn’t just an American game—Sam has brought his act to Europe, Asia, and beyond. 🌍✨ 🔹 His Love for Japan & Scandinavia: Why he keeps going back, what makes those places special, and what he’s learned from their cultures. 🍣🇯🇵🏔️🇳🇴 🔹 His Own Travel Show?! Sam teases a potential new project where he brings his comedic lens to international exploration. 👀📺 🎙️ THEN… Barstool Beef on Being a BIG, BIG Traveler 🏋️‍♂️💼 @BarstoolBeef joins the crew to talk about the unique challenges of traveling as an absolute unit. 💪😅 🔹 The Airline Struggle: Which airlines are the best (and worst) for larger passengers? Where can a big man get some elbow room?! 💺✈️ 🔹 Packing Tips for XXL Life: Finding clothes that fit, packing efficiently, and dealing with tiny hotel closets. 🎒👕 🔹 Seatbelt Extenders, Tiny Hotel Beds & Cramped Spaces: The unspoken realities of big-guy travel—how to avoid awkward moments & what hacks make it easier. 🛏️🤯 🔹 Best Destinations for Big Guys: Which places are actually comfortable for larger travelers? Spoiler: Some spots are NOT built for a 6’5”, 300+ pounder. 🌎😅 🔥 This episode has it all—comedy, travel tips, chaos, and a deep appreciation for Sam Tallent’s journey. 💬 Let us know—what’s the worst travel experience you’ve ever had?! Drop it in the comments! Try your first month of BlueChew FREE. Visit https://BlueChew.com for more details and important safety information, and we thank BlueChew for sponsoring the podcast. Find your perfect pair at https://www.heydude.com today! 🎧 Listen Now: 📍 Apple Podcasts | Spotify | YouTube 📲 Follow & Subscribe: @BarstoolSports | @DropAPinPod #DropAPin #ComedyTravel #SamTallent #BarstoolBeef #BigGuyTravel #Japan #Scandinavia #TravelTips #BarstoolSports

Billy Football Breaks His Silence on Future at Barstool (And Africa) | Drop A Pin Ep. 19 Episode Breakdown: ✅ Billy Football Returns! 🏟️🎤     •    Why he left Barstool & what he's been up to     •    Coaching football in Africa 🏈🌍     •    His wild adventures in Botswana 🇧🇼🐘 ✅ Getting Cultured w/ Jon Gruden 🏆🔥     •    Coaching football in Europe 🏈🇪🇺     •    Where he wants to vacation next (hint: NOT Oakland 😆)     •    His thoughts on the global growth of football 📲 Follow Us: 🔹 Drop A Pin: [@DropAPinPod] 🔹 Donnie: [@DonnieDoes] 🔹 Chaps: [@UncleChaps] 🔹 Billy Football: [@Billyhottakes] 🔹 Jon Gruden: @barstoolgruden #DropAPin 🌍 #BillyFootball #JonGruden #Football #Travel #Botswana #NFL #BarstoolSports #Podcast