You’ve may have heard of John W. Henry—billionaire owner of the Boston Red Sox and Liverpool Football Club, a guy who’s got sports locked down tight. But before he was swinging bats and kicking goals, he was swinging trades in the only arena that really counts: the markets. And here’s the kicker—he didn’t get there by guessing what’s next.
Henry stacked his multi-billion fortune doing what most investors won’t stomach: riding trends, not chasing hot tips. His story’s a neon sign screaming one truth—prices call the shots, not people.
Most traders are junkies for predictions. They’re glued to forecasts, sweating over Fed moves, betting some talking head on TV’s got the future figured out. Henry? He didn’t play that game. He cashed in because others thought they could outsmart the market—and crashed hard. His gig wasn’t about knowing the next move; it was about jumping on when it happened.
1995: Barings Bank imploded betting against the tide. Henry was on the flip side, pocketing their losses like it was nothing.
2002: NASDAQ’s bleeding out, and Henry’s up 40%. No voodoo—just following the price.
2008: World’s falling apart, and Henry’s system’s raking it in while everyone else is toast.
2025: Are you ready for the next big trend up or down? Are you ready for the next black swan?
Markets trend because people don’t change—greed, fear, panic, rinse, repeat. Henry saw that pattern from the 1800s to now and built a machine to ride it.
Henry didn’t roll out of some Wall Street penthouse. He’s a Midwest kid who grew up crunching baseball stats and outsmarting blackjack tables. No fancy degree, just a head for numbers. That’s how he tackled markets—not as a guessing game, but a straight-up quant hustle where he learned sticking to a plan beats flapping your gums.
His playbook? Dead simple:
Ride Big Trends: Tune out the daily chaos, grab the monster moves.
Stay Cold-Blooded: No hunches, no tears—just the system.
Manage the Hits: Dump the duds quick, let the winners roll.
Go Wide: Trade anything, anywhere—don’t bet on one pony.
Winning wasn’t about being the sharpest tool in the shed. It was about ditching the dumb stuff—emotions, hot takes—and sticking to what works.
Henry pulled the plug on his trading firm in 2012, and some folks cried “failure.” Come on. By then, he’d already banked billions and flipped the script to sports mogul mode—Red Sox, Liverpool, the works. He didn’t lose; he leveled up.
His Trend Following legacy? Ironclad. Thirty years of crushing it, proving markets don’t care about your theories—they trend anyway. People still screw up the same way. The cash is still up for grabs. You just gotta see it.
Henry nailed it in trading and sports with one rule: the numbers don’t lie, noise does. Soybeans or strikeouts, same deal—trust the data, ditch the chatter. He said it best: “We don’t predict the future, but we know it won’t look like the past. It never does.”
Most traders tank because they’re hooked on playing psychic. Henry didn’t. He followed the game billionaires play. You still waiting for some guru to spoon-feed you the next big thing? Or you ready to step up and trade what’s real?
How can you move forward immediately to Trend Following profits? My books and my Flagship Course and Systems are trusted options by clients in 70+ countries.
Also jump in:
• Trend Following Podcast Guests
• Frequently Asked Questions
• Performance
• Research
• Markets to Trade
• Crisis Times
• Trading Technology
• About Us
Trend Following is for beginners, students and pros in all countries. This is not day trading 5-minute bars, prediction or analyzing fundamentals–it’s Trend Following.
