TGIT: We Have an Issue with Gambling Stocks

March (market) Madness, billionaire bets, DFKG, MGM, CZR, FLUT, TTWO, Zero DTE tactics, high-octane ETFs, Mike finds his whiteboard, Sosnoff rants, a new Rising Star and more. First time reading? Join other risk-takers, entrepreneurs, traders, investors, data geeks and alpha types. Sign up for free here.

TGI Thursday! (10/27) Apple introduced the slogan “there's an app for that” 16 years ago to promote the iPhone's endless possibilities. Fast forward to yesterday when Sports Illustrated announced SI Predict, a sports wagering platform where "there's a bet for that"—as long as you're not betting on the actual outcome of a game.

Not your father's sports book, SI Predict will exist in the fertile space between gambling and "predictive markets” like Polymarket and Kalshi. Instead of taking bets on who’ll win a sporting event and by how much, it enables users to wager on happenings and outcomes "adjacent" to the game—things like stadium attendance, halftime performers' playlists and seating arrangements in Taylor Swift's suite. Think of it as sports betting's answer to derivatives trading. The platform declares itself to be above the regulatory fray because of its non-custodial structure—a neat trick that's about as convincing as a casino claiming it's just a social club.

But we’re having no difficulty identifying attractive trading opportunities in the midst of March Market Madness, uncertainty around Trump’s looming April 2 tariffs and an indecisive rebound from the market's recent correction. No bookie required.

Stay lucky!

Editorial Director

Beyond Brackets:
America's Hidden Gambling Obsession 

While March Madness captures headlines with its multi-billion dollar betting binge, a far more startling statistic lurks beneath the tournament frenzy. Americans aren't just casual wagerers during basketball season—they're year-round gambling junkies. The percentage of adults feeding their daily online betting habit would shock even the most jaded Vegas veteran. Men particularly can't seem to keep their fingers off the betting apps, outpacing women by nearly double. As states frantically legislate brakes for this runaway train of digital wagering, the question remains: When the buzzer sounds, what’s the true cost of this national pastime? Read Full Story

DraftKings' March Madness Mathematics

DraftKings (DKNG) leads the charge as March Madness betting surges to a projected 14% increase over last year. The stock presents both opportunity and risk. With an Implied Volatility Rank of 30, options traders are eyeing strategic positions, particularly in May 16 expiration puts offering 70% probability of profit. Read Full Story

Traditional Casino Stocks:
Oversold and Ready for a Rebound? 

While investors have gone all-in on gambling apps, sending FanDuel parent Flutter (FLUT) up 14%, they've simultaneously folded on Vegas icons MGM (MGM) and Caesars (CZR) — both down a staggering 30% despite robust digital growth of their own. This market disconnect has created what might be the gambling sector's most compelling opportunity. With MGM trading at just 13 times earnings (well below the sector's 18x median) and analysts maintaining price targets 50%-70% above current levels, these beaten-down casino giants may be poised for a dramatic reversal. Read Full Story

FanDuel, owned by Flutter Entertainment, generated $5.79 billion in revenue in 2024, up 20% YoY.

— Business of Apps

Think you know where the smart money is flowing in the gambling world? Think again. While industry stalwarts Caesars, DraftKings (DKNG) and PENN Entertainment (PENN) managed to squeeze into the top 10 casino stocks ranked by billionaires’ investments, they've been outflanked by five less-trumpeted contenders commanding even greater financial firepower from America's wealthiest investors. With the global gambling and casino market projected to explode from $310 billion to a staggering $512 billion by 2032, these 10 casino operators have attracted billions in investments from financial titans. The No. 1 ranked stock on this list has 19 billionaires as investors totaling more than $3.2 billion. Read Full Story

When we ask tastylive Rising Stars how they learned to make money by trading options, their most common response is “Mike and His Whiteboard!” Options trader and educator Mike Butler debuted the series in 2016, and by now it’s segments have been viewed more than 8.6 million times on YouTube alone.

This Saturday, Butler and his merry band of traders are ready to display their whiteboard wizardry on strike and expiration manipulation as they escort you deep into the abyss of options. "Buying the guts and selling the wings" isn't a cannibalistic ritual—it's your ticket to financial liberation in this ruthless market. To attend, sign up here before 10 a.m. CDT on Friday, March 29.

Veteran traders Tom Sosnoff and Tony Battista share new research from tastylive which may have identified the holy grail of zero DTE trading: 20-delta iron condors with $10 wings. This repeatable strategy has been delivering a 90% win rate when profits are snatched at 25% of maximum potential. Over the past two years, this simple structure offers defined risk around $800 per contract—making the SPX playground accessible without sacrificing probability. Watch the video here.

While the S&P 500 slumps and gaming rivals flounder, Take-Two Interactive (TTWO) has quietly orchestrated a stock surge that's leaving investors wondering what cheat code they've activated. The answer lies in the most anticipated video game release of the decade—GTA VI—a title so powerful that mere speculation about its release is already moving markets. With previous installments selling hundreds of millions of copies, the Street is betting lightning will strike again for the company behind gaming's most notorious franchise. And trader Thomas Westwater has a plan for those directionally inclined. Read Full Story

Physician and Rising Star trader Azhar Pasha reveals how he transformed $2 million into a $24 million portfolio, primarily using Zero DTE options strategies. After losing $4 million in a devastating market drop, he doubled down against all advice, depositing $10 million more. Now managing 100+ positions with 60% in naked options, he has generated 20%-40% annual returns while still practicing medicine full-time. Learn his approach to selling premium and why he believes market volatility creates the perfect trading opportunity. His story and video are here.

Recent market turbulence has ushered in a new landscape for traders, and if you're not using inverse and leveraged ETFs, you may be missing out on a powerful way to capitalize on volatility. Whether you're looking to profit from market declines with inverse ETFs, or amplify gains during a quick market rebound with leveraged ETFs, these financial tools offer high-risk, high-reward opportunities to capitalize on these sharp fluctuations. These instruments demand active management and quick decision-making, making them suitable primarily for experienced traders with clear short-term strategies. Read Full Story

Since 2018, legal sports betting has exploded into a $120 billion beast that's systematically devouring household finances. New research reveals the brutal math: For every dollar pumped into betting apps, nearly a dollar vanishes from investment accounts. The casualties? Savings accounts, credit scores and financial futures—particularly among those who can least afford the loss. This isn't just entertainment; it's a structural force reshaping American finances. Read Full Story

Options trading veteran Tom Sosnoff isn't buying the crypto Kool-Aid that GameStop (GME) and Trump are serving. In the latest installment of the popular Truth or Skepticism video podcast, Sosnoff and his co-host, author and pundit Dylan Ratigan, deliver a blistering critique of what some might consider cryptocurrency innovations. The pair look askance at a lackluster video game retailer spending its extra cash on bitcoins instead of using it to improve its own operations. They also take a dim view of an American president pursuing his stablecoin dreams because it makes him the issuer of the currency and also the regulator of the currency. Watch the video here.

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How Luckbox editors manage to drink for free.
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Consumer confidence hits a 12-year low.

Why men beat women at Scrabble. 

ICYMI: Last week’s Luckbox TGIT. 

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