The 1996 Chicago Bulls didn’t just win an NBA championship—they dominated with a 72-10 record that stood as the league’s best for two decades. But beyond the highlight reels and championship parade, that legendary roster offers a surprisingly elegant framework for thinking about modern portfolio design.
At a Lunch n Learn sponsored by RCM and CME Group for RIAs in Brentwood, Tennessee last week, this Bulls analogy became the centerpiece of a fascinating discussion about modern portfolio construction.
The Starting Five: Traditional Portfolio Roles
When Mike Philbrick described the Bulls’ roster as “Jordan, Pippen, Kerr, Longley, and Rodman,” the Chicago-based true Bulls fanatics in the room had to gently correct our Canadian friend. Close, Mike—but Kerr was actually the sixth or seventh man off the bench, along with Toni Kukoc as the other notable reserve. The real starting five was Jordan, Pippen, Ron Harper, Longley, and Rodman.
Still, the metaphor works beautifully. Think of Michael Jordan as your Nvidia—the high-flying, high-scoring superstar that captures everyone’s attention and delivers explosive performance. Scottie Pippen plays the steady, reliable role of the S&P 500, consistently delivering solid returns while complementing the star. Steve Kerr becomes your Russell 2000, adding crucial performance at key moments when you need it most—even if he had to wait for Phil Jackson to call his number.
Then you have your defensive anchors. Luc Longley is your bond allocation—steady, reliable, unremarkable, but essential to the structure. And Dennis Rodman? Tattoos, dyed hair and all, he’s your game-changing, non-correlated alternative investment. Rodman didn’t just zag when others zigged—he preferred it that way. While everyone else chased points, he owned the boards, turned defense into offense, and brought a completely different skill set that made the entire system work better.
Breaking the Five-Player Rule
Here’s where Philbrick’s insight truly shines: “What if you could put Kukoc in and leave Jordan on the floor?” Better yet—what if you could also put Kerr in the game, now having all the stars we remember playing at the same time? In basketball, you’re limited to five players on the court. But in modern portfolio construction, return stacking strategies allow you to essentially play with six, seven, or even ten players at once—combining beta exposure with alternative strategies in a single ETF structure.
Bill Marr of Welton shifted the sports metaphor to football, talking about the different pieces of a portfolio like the different parts of a football team. Everyone knows all about the offense—that’s your stocks. They try to do defense, if not perfectly, with bonds. But most investors forget about special teams—the non-correlated alternatives that fill in the unseen gaps in the main game plan and can make the difference between a winning team and a championship team. His approach to combining active equities with managed futures is “like putting all three on the field at the same time,” he explained. It’s not allowed in football, but in modern finance, it’s not just possible—it’s increasingly accessible through innovative product structures.
When Theory Meets History
Brian Stutland, whose volatility investing Equity Armor fund is outpacing the S&P 500 this year, brought the metaphor full circle with a personal touch. He shared how a friend snuck a young him into the Bulls’ 1997 championship game—the one where Steve Kerr hit the winning shot off a Jordan assist. That moment captured the essence of complementary roles: the superstar creating the opportunity, the specialist delivering the crucial return. In his fund, when the opposing defense shuts down the (stocks) superstar, long volatility steps up to hit the winning shot.
It’s a powerful reminder that championship portfolios, like championship teams, aren’t built on star power alone. They’re built on strategic combinations that let different assets play their roles simultaneously—something that traditional portfolio construction rules said was impossible, but modern strategies are making routine.
