In May 2017, I sat down with Kenny “The Jet” Smith on Scoop B Radio to discuss one of the most polarizing “what ifs” in basketball history: the mid-90s Orlando Magic. At the time, the NBA world was still dissecting why a team with two of the most dominant young forces in sports history—Shaquille O’Neal and **Anfernee “Penny” Hardaway”—only made one Finals appearance before splintering.
Today, in 2025—as we watch “super-teams” struggle to find chemistry—Kenny’s “buttoned-up” assessment of Orlando as a “missed dynasty” serves as a cautionary tale of ego, management, and timing.
The Blueprint for Dominance
Kenny, who faced the Magic in the 1995 NBA Finals while playing for the Houston Rockets, had a front-row seat to their potential. He argued that the combination of Shaq’s physical gravity and Penny’s perimeter wizardry was a prototype for the modern game.
“They were the most talented team we played,” Kenny Smith told me. “Shaq was a force of nature, and Penny was 6’7″ doing things at the point guard spot that we hadn’t seen since Magic Johnson. They had everything you needed to win four or five titles.”
In 2025, we look at Penny Hardaway as the spiritual ancestor to players like Luka Dončić or Shai Gilgeous-Alexander—tall, cerebral playmakers who could score at all three levels. Kenny’s point was clear: Orlando didn’t lose because they lacked talent; they lost because they didn’t have the “internal infrastructure” to survive their own success.
The 1995 Finals: A Psychology Lesson
The 1995 Finals is often remembered as a “sweep,” but as Kenny pointed out, the margins were razor-thin. The “missed free throws” by Nick Anderson in Game 1 didn’t just lose a game; it broke the team’s spirit.
“If they win Game 1, that series goes seven. They might even win it. But when you’re that young, you don’t know how to recover from a heartbreak like that. We [the Rockets] were veterans; we knew how to take advantage of that crack in the door.”
Looking back from 2025, that series is a case study in Championship DNA. The Rockets had it; the Magic were still trying to buy it. Kenny’s insight highlights that a dynasty requires more than just two stars; it requires a supporting cast that can withstand the psychological pressure of the biggest stage.
The Breakup: Management’s Fatal Error
The “missed dynasty” became official in 1996 when Shaq left for the Los Angeles Lakers. Kenny was candid about how the Magic organization mishandled their most valuable asset.
“You don’t let a guy like Shaq walk. You don’t let him feel unappreciated. That’s the biggest mistake in NBA history. If they stay together, the Lakers dynasty of the 2000s happens in Orlando instead.”
Reflecting on this today, the parallels to modern free agency are striking. Kenny saw early on that the relationship between a superstar and the front office is just as important as the relationship between the stars on the court.
2025 Retrospective: The Legacy of “What If”
Today, the 1990s Orlando Magic are remembered for their iconic pinstripe jerseys and the “Lil’ Penny” commercials, but for basketball purists like Kenny Smith, they represent the ultimate “Unfinished Symphony.”
| Category | Shaq & Penny (Orlando) | Shaq & Kobe (Lakers) |
| Finals Appearances | 1 (1995) | 4 (2000-2002, 2004) |
| Championships | 0 | 3 |
| Longevity | 3 Seasons Together | 8 Seasons Together |
Kenny Smith’s 2017 session on Scoop B Radio was a reminder that in the NBA, talent gets you to the door, but character and management get you through it. He taught us that while the Rockets won the rings, the Magic provided the biggest “What If” of a generation.
