Michael Jordan couldn't win 6 rings today

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We’re kicking off the new year with an old musing. A musing requested by many of you:

Could Michael Jordan win 6 rings in today’s NBA?

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Michael Jordan is the best basketball player who’s ever lived, but that’s not what made the Bulls a dynasty from 1991 to 1998. The dynasty happened because Jordan played in a league where continuity was cheap, leverage moments were rare, and team-building wasn’t punished by the salary system.

But dynasties aren’t just about talent. They’re about timing, rules, incentives, and how a league wants its labor market to behave.

Fast forward to the modern NBA (2012–2020), the LeBron era of player mobility. Contracts are shorter. Max salaries compress superstar earnings. Trade requests became negotiation tools. And luxury-tax math makes keeping an elite core together an exercise in financial gymnastics.

The following is not up for debate: Jordan would still be the best player in any era.

But could one franchise keep a Jordan-led core intact long enough for six titles under modern cap rules?

I. The Jordan Era: 1988–1998 — Continuity Was the Default

1. Free agency was new, and star relocation was extremely rare.
Unrestricted free agency began in 1988, but stars didn’t treat it as a relocation tool. Movement was slow, cautious, and often financially irrational by today’s standards.

2. Long contracts meant fewer leverage points.
Players signed 6–8 year deals with no player options and minimal opt-out flexibility. A star could go half a decade without a meaningful “decision moment.”

3. The 1995 Rookie Salary Scale locked in cheap, elite talent.
Teams gained cost certainty over Pippen-/Kukoc-level players, allowing them to maintain roster continuity without sacrificing flexibility.

4. Bird Rights + Soft Cap = Retention Advantage.
Teams could exceed the cap to re-sign their own players, giving incumbents meaningfully more power than rivals.

Bottom Line: Continuity to keep teams together was baked into the league.

II. The Modern NBA: 2012–2020 — The System Favors Mobility

1. The 2011 CBA shortened maximum contracts.
Five years for Bird players, four for everyone else.
This immediately increased leverage cycles by ~40%.

2. Max salaries compress superstar value.
Since a superstar can’t be paid true market value, the financial gap between staying and leaving is small. Players optimize for teammates, market, and contention instead.

3. Trade demands became viable bargaining tools.
Unlike the ’90s, modern stars use public trade requests to dictate destinations. Teams push back, but the dynamic creates instability.

4. The luxury tax destroys multi-year depth.
Keeping a Jordan-Pippen-Kukoc core becomes a tax-apron nightmare.

5. The Supermax attempted to buy back continuity — and failed.
It keeps the superstar, but it destroys the supporting cast.

III. Power Dynamics: From Team Planning to Player Optionality

1988–1998:
Teams controlled time horizons. Continuity was cheap. Extensions were predictable. And the media ecosystem didn’t accelerate trade storylines.

2012–2020:
Owners won the macro financial fight (BRI share). Stars won the micro leverage fight (short deals, opt-outs, trade requests, media platforms).

The result is a league where teams have revenue certainty, but NOT roster certainty.

IV. Would Jordan Build a Dynasty Today?

Jordan would win championships in any era.
That is NOT the question.

The question is whether a franchise could keep his core intact long enough to win six titles in eight years.

Here’s why it maybe doesn’t happen:

• A modern Pippen becomes a max free agent twice before the second three-peat.

• Third stars become tax casualties.

• Depth erodes under repeater-tax math.

• The media/agent ecosystem transforms every contract decision into leverage.

Verdict
Jordan would dominate the modern NBA.
But the Bulls dynasty as we know it?
It would require flawless drafting, perfect tax tolerance, and elite CBA navigation.

The ’90s Bulls had all those things — but they also had something today’s teams don’t:

A league designed to let you stay together.