Michael Jordan vs. Kobe Bryant

Michael Jordan and Kobe Bryant are two of the best ever to play in the NBA.  The legacy of the two players is incredible; Jordan has 6 Championships, led the league in Win Shares 9 Times, was named to 14 All-Star Teams, captured 6 Finals MVPs & 5 Regular Season MVPs.
Bryant has 5 Championships, was named to a record 18 All-Star Teams, 2 Finals MVPs & 1 Regular Season MVP.

As others have noted, Jordan was a more productive player when on the court - and although the degrees of "being better" vary, he was better in virtually every meaningful way. However, that last phrase "when on the court" is key.  Bryant was named to the All-NBA Team 15 times, while Jordan was "only" named 11 times.  This gives us 4 extra seasons where Bryant played at a high level - and Jordan didn't play at all.  What Bryant lacks in relative quality, he may be able to make up in quantity.

What we're really interested in answering here is this question:  Who had the more impactful career?  To estimate that, we're going to use my lineup simulator tool - and have Jordan & Bryant literally switch careers to project how each might have done in the other's shoes.  Each player will progress through each other's career with the exact same teammates as the other one had.

The tool will help us understand a reasonable projection of wins by season and by looking at the incremental benefit (or loss) that each player provided over the other.  When we evaluate playoff performances, the tool will help us understand if the difference between the two players is large enough to swing any playoff series.  In series where the two teams never met, the lineup simulator will score the teams against each other.  Make sense?  Let's get started.  Narrative Commentary provided from here on out is my own and is fictional based on the circumstances and my subjective opinions.  The quote from O'Neal preceding the 2003 season is, however, real.

1985

Kobe Bryant joins the Chicago Bulls straight out of High School and joins a Bulls team that had gone 27-55 the year prior.  As an 18 year old rookie, Bryant is not yet equipped to have a huge impact as Chicago struggles to a 29-53 finish; missing the playoffs.
Actual result:  38-44, 1st round exit.

1986

Bryant improves and takes a leap forward becoming one of the best players on the Bulls.  The Bulls make the playoffs at 32-50, but are swept in the 1st round by a juggernaut Celtics team.

Actual result:  30-52, 1st round exit.

1987

The young Bulls struggle to another 50 loss season going 31-51.  However this does earn them the right to get swept for the 2nd straight year by Boston.

Actual result:  40-42, 1st round exit.

1988

Bryant takes a step forward, making his first all-star team.  The team adds Scottie Pippen and Horace Grant via the draft and the young Bulls show promise finishing over .500 at 42-40.  Chicago earns home-court advantage in the 1st round and defeats Milwaukee.  In the 2nd round they are matched up against the Celtics and are sent home in 5 as Boston defeats Chicago for the 3rd consecutive year.  Bird snidely mentions that how the Bulls are a "cute" team.  

Actual result:  50-32, 2nd round exit.

1989

Bryant's sidekick, Charles Oakley is traded for Bill Cartwright.  This off-sets gains made by Pippen & Grant.  Chicago fails to advance in the standings going just 40-42 and squeaking into the playoffs as the #8 seed.  Eventual champion Detroit sweeps them in the first round.

Actual result:  47-35, Conference Finals appearance

1990 

The team makes a large step forward in the regular season finishing 49-33 and earning home-court in the first round.  The team has lofty expectations for the playoffs but they fail to materialize as the Bulls are upset in 5 by the Knicks as Patrick Ewing has a monster series.

Actual result:  55-27, Conference Finals Appearance

1991

Everything comes together; Scottie Pippen & Horace Grant continue to progress as does Bryant. The Bulls finish 57-25, earning their first division title and the best record in the Eastern Conference while Bryant earns his first MVP.  The Bulls exact vengeance on the Knicks in a sweep and do the same to Detroit in the Conference Finals, ending their reign.  The Lakers pose a formidable threat in the Finals but injuries to James Worthy & Byron Scott weaken the Lakers as the Bulls win in 5.

Actual Result:  61-21, NBA Championship

1992

The Bulls continue their regular season dominance, going 61-21 and repeating as Division Champs.  However, Bryant faces distractions from an ongoing rape trial that takes place over the season as Scottie Pippen delivers a better overall season.  Clyde Drexler wins MVP as Pippen/Bryant split the vote from Chicago.  The Bulls are easily able to dispatch Miami in the first round but are stunned in the 2nd round by the Knicks in 6.  Cleveland goes onto defeat Portland in the Finals and fans are unsure what to make of the strange season.  

Actual result:  67-15, NBA Championship

1993

Bryant has his worst season of the 90's, as his play drops off again.  Pippen again paces the team.  The Bulls struggle to a 49-33 record and cede the Division Title to Cleveland as the Bulls settle for the 3 seed.  Chicago manages to defeat the Cavs in 7 but falls to the Knicks for the 3rd time in 4 years in the Conference Finals.  The Knicks would go on to be defeated by Phoenix in the Finals.  In the off-season Chicago is regarded as a team in turmoil and trade rumors swirl around Bryant - some wonder if his best days are behind him.  After 3 playoff victories over the Bulls in 4 years, Patrick Ewing is considered superior to Bryant.  

Actual result:  57-25, NBA Championship

1994

Bryant re-dedicates himself to his craft in the off-season and comes back with a vengeance, leading the league in scoring while leading the Bulls to the best record in the Eastern Conference at 60-22 and re-capturing the Division Title.  The Bulls sweep through the first round and dispatch an upstart Indiana Pacers team in 6.  In the Conference Finals, the Bulls find themselves matched against a familiar foe, the New York Knicks.  This time, the Bulls are able to push past the Knicks in 5 and set themselves up for a Finals matchup with Houston.  While Olajuwon dominates inside, Bryant & Pippen are too much to overcome, as Chicago wins in 6 - a storybook ending for the fabled Chicago Stadium.

Actual result:  55-27, 2nd round exit

1995

Horace Grant departs to Orlando, cutting the Bulls' margin for error.  Chicago takes a slight step back, finishing 54-28 but still capturing the Division title.  After eliminating a fading Cavs squad in the first round, the Bulls once again find themselves face to face with the Knicks.  For the 2nd straight year, Chicago is able to over-come the Knicks.  This sets up a showdown with the young Orlando Magic in the Conference Finals, led by Shaquille O'Neal & Anfernee Hardaway.  The combination of Bryant & Pippen on the perimeter are able to off-set the damage Shaq does inside as the Bulls win in 6.  In the Finals, Chicago finds itself in a re-match with Houston, who has now acquired Clyde Drexler in a trade with Portland.  Olajuwon & Drexler know the clock is ticking on their chances and fight valiantly but Chicago repeats as Champions, christening the United Center with a Championship Banner.

Actual result:  47-35, 2nd round exit

1996

Despite the Bulls' Championship run, management recognizes that interior defense & rebounding are weaknesses.  These are addressed in the form of Dennis Rodman.  Expansion dilutes the talent pool and Chicago sets an NBA record for wins, finishing 70-12 as Bryant captures his 2nd MVP.  Chicago follows a similar path to the Finals - eliminating the Knicks & Magic in 5 each before capping off their 3rd consecutive championship run with a Finals win over Seattle.

Actual result:  72-10, NBA Championship

1997

A new power rises in the West.  Shaq departs the Magic for the bright lights of LA and the Lakers are able to acquire a talented rookie by the name of Michael Jordan.  With these new weapons, the Lakers rise out of the West going 61-21 and capture the Pacific Division Title. Despite Shaq being slowed by injuries, the Lakers are able to knock off the Jazz in the Conference Finals.  They would be met by the veteran 67-15 Chicago Bulls in the Finals.   The series would be regarded as an all-time classic going 7 games as Chicago was able to narrowly hold off the young Lakers.  Excitement was building for a Bryant-Jordan rivalry and while narrowly defeated, the Lakers were regarded as the team for the future.

Actual Bulls result:  69-13, NBA Championship

Actual Lakers result:  56-26, 2nd round exit

1998

The Lakers entered the season as favorites but an ankle injury to Michael Jordan derailed their plans.  Jordan could have came back for the playoffs, but owner Jerry Buss put his foot down taking the long view.  Nevertheless, the Lakers had plenty of talent and still went 61-21. However, without Jordan, they were defeated by Utah in the Conference Finals as Malone & Stockton finally made a Finals.

In the East, the Bulls struggled through a season where both Bryant & Pippen missed time, finishing 56-26 and 2nd in the Division to the Pacers.  After ousting the Knicks for the 4th time in 5 years in the 2nd round, Chicago wrestled with the challenging Pacers in the Conference Finals and narrowly survived a game 7 in Indianapolis.  In the Finals, Chicago was able to defeat the Jazz in 6 as Chicago pulled off their 5th straight championship.

Actual Bulls Result:  62-20, NBA Championship

Actual Lakers Result:  61-21, Conference Finals Appearance

1999

Bulls GM Jerry Krause inexplicably decided to break the Bulls up.  The Bulls were battle weary and Pippen had looked like a shell of himself in the playoffs, but it still shocked pundits that Krause was so willing to break up a dynasty.  Bryant was sent packing to a Washington team that was full of past their prime stars.  Bryant dragged the team to mediocrity, finishing 24-26 but missing the playoffs for the first time in over a decade.   Jordan returned and led the league in scoring while capturing his first MVP, driving LA's high powered offensive attack.  However, the Lakers didn't need more offense, they needed defense.  After trading Elden Campbell & Eddie Jones for Glen Rice, the Lakers were soft defensively.  Despite finishing 36-14 and capturing the Pacific Title, they were surprised in the 2nd round by the aging but fundamentally sound Jazz who finished 37-13.  San Antonio went on to win the Championship.

Actual Wizards Result:  18-32, missed playoffs

Actual Lakers Result:  31-19, 2nd round exit

2000

Once hated for his arrogance and off court behavior, the aging Bryant drew sympathy as he squeezed 38-44 out of a weak Washington roster.  In Los Angeles, Jordan focused on making his game more well rounded and became a more efficient all-around player. Shaq would have the best season in his career, finishing 2nd in the MVP race to Michael Jordan and the Shaq/Jordan combo was devastating.  With Jordan & Shaq submitting all-time great seasons, it was the perfect storm as Los Angeles dominated the league with a record setting 75-7 performance and winning Jordan & Shaq's first championship.

Actual Wizards Result:  29-53, missed playoffs

Actual Lakers Result:  67-15, won NBA Championship

2001

Washington completely falls apart and Bryant starts to fade a little.  It's all Bryant can do to avoid the cellar as the Wizards finish 27-55, just one game ahead of last place New Jersey. Bryant tears his ACL at the end of the season and the question is asked, "Is this the end?" Meanwhile, the Lakers continue their dominance finishing 63-19 and going undefeated in the playoffs as Jordan & Shaq continue their elite level of play.  Jordan captures his 3rd MVP.

Actual Wizards result:  19-63, missed playoffs

Actual Lakers result:  56-26, won NBA Championship

2002

The Wizards start to upgrade their roster going 35-47 as Bryant recovers from ACL Surgery.  Jordan paces LA to a 64-18 year.  Shaq misses 15 games with injury and despite the Lakers winning their 3rd consecutive championship, the first signs of cracks in the Jordan/Shaq relationship appear as Jordan begins to question Shaq's conditioning and dedication.  On the other hand, Shaq is jealous of the attention Jordan receives as Jordan earns his 4th MVP.

Actual Wizards result:  37-45, missed playoffs

Actual Lakers result:  58-24, won NBA Championship

2003

Bryant returns but has trouble staying on the court.  He is clearly not the Bryant of old and struggles through the season as Washington finishes 34-48.  The Jordan/Shaq relationship continues to fissure as Shaq pushes a toe surgery to the pre-season and misses the first 15 games saying "I got hurt on company time, so I'll rehab on company time."  The supporting cast has aged at this point and there is little support around the Jordan/Shaq duo.  Jordan is still dominant but Shaq has to play his way into shape and the aging core offers little in the way of support as the Lakers slip to 54-28. The Lakers remain a high powered offensive machine but are mediocre defensively - losing the Division Championship to Sacramento and are defeated in 7 by the more well-rounded Spurs in the 2nd round.  The Spurs would go on to win the title.

Actual Wizards result:  37-45, missed playoffs

Actual Lakers result:  50-32, 2nd round exit

2004

Washington is in the middle of a youth movement, which Bryant doesn't fit in to well.  He no longer adds value to Washington and they struggle in a 26-56 season, missing the playoffs.  Bryant retires after the season but scores 60 in his final game.  Bryant is recognized as one of the all-time greats and many argue that he is the best ever.  At minimum, the consensus is that he is the best player of the 90's. 

The Lakers attempt to re-load by adding veterans Karl Malone, Gary Payton & Horace Grant to the team.  The Jordan-Shaq relationship hits another bump as Shaq calls out owner Jerry Buss in a pre-season game screaming "Pay me!". Despite injuries to Shaq & Malone, the Lakers re-capture the Division Title winning 61 games. The Lakers push aside the Sacramento Kings in the 2nd round and eliminate the Spurs in the Conference Finals as Jordan takes out his frustration in Garnett winning the MVP. LA enters the Finals against Detroit as heavy favorites but are upset in 7 games as Detroit's defense is suffocating.  Jordan & Shaq have no help and Detroit's well balanced attack carries the day.

Actual Wizards result:  25-57, misses playoffs

Actual Lakers result:  56-26, loses in Finals

2005

Shaq departs as the Jordan-Shaq marriage comes to an end; Gary Payton & Karl Malone also leave the Lakers, who are now in rebuild mode.  Jordan is able to carry an over-matched Laker roster to a respectable 43-39 record, but the Lakers miss the playoffs in a hyper-competitive Western Conference.  At this point, Jordan is frustrated.

Actual result:  34-48, misses playoffs

2006

Jordan walks away from the NBA, pursuing baseball instead.  The Lakers finish 35-47 as they miss the playoffs for the first time in over a decade.  Shaq wins a championship in Miami, albeit Wade is the best player.  Despite being the 2nd best player on a title team again, Shaq crows that he is better than Jordan and claims Wade is the best shooting guard ever.

Actual result:  45-37, 1st round exit

2007

After hearing Shaq talk trash saying that he was the real reason Los Angeles won all those titles, Jordan returns mid-season but the Lakers are too far back to have any real hope of making the playoffs.  The Lakers finish 33-49.

Actual result:  42-40, 1st round exit

2008

With a full season under his belt and the addition of Pau Gasol, Jordan leads the Lakers to a 58-24 and have the best record in the West as Jordan captures his 5th MVP.  During the All-Star break, Shaq taunts Jordan saying "Tell me how my ass tastes"* as Shaq feels superior to Jordan with an extra ring under his belt.  Center Andrew Bynum gets injured mid-way through the season, sapping the Lakers of interior defense & rebounding.  The Lakers cruise to the Finals anyway but are defeated by Boston in a tough 6 game series as Kevin Garnett, Paul Pierce & Ray Allen win their first NBA Title.  

Actual result:  57-25, loses in Finals
The quote from Shaq is authentic; at the time it was referenced towards Kobe Bryant.  For narrative purposes, I've adapted it to be directed towards Jordan.

2009

The Lakers have better luck with health this year and dominate the league, finishing 67-15.  Although the Lakers show vulnerabilities to quicker point guards as Houston & Denver pose stronger than expected challenges, the Lakers still are able to capture their first title since 2002.

Actual result:  65-17, NBA Championship

2010

Los Angeles gets back to the Finals again with ease, going 63-19.  In the Finals, they face a re-match from 2008 against Boston. This time, they are able to dispatch the Celtics in a grueling 7 game series.  Jordan announces his retirement in the off-season.  He is the consensus best player of the decade and has eliminated any doubts that he can win without Shaq. While there is some debate over whether Jordan had a better career than Kobe, there is agreement that Jordan was the most dominant player at his peak and it is accepted that prime Jordan was better than prime Kobe or prime Shaq.  When Jordan is asked in his retirement press conference who was better - him or Shaq, he simply responds by saying "last time I checked, I'm the one with the 5 Finals MVPs".  

Actual result:  58-24, NBA Championship
The above Jordan quote is fictional

2011

Although Jordan is gone, the Lakers are still a capable team, finishing 51-31, capturing the Pacific title for the 4th straight year.  After getting past Denver in the 1st round, the Lakers are eliminated by the Spurs in the 2nd.

Actual result:  57-25, 2nd round exit

2012

The Lakers are aging but still a force to be reckoned with and finish 37-29 in a lock-out shortened season.  However, the younger more athletic Oklahoma City Thunder sweep Los Angeles in the 1st round.

Actual result:  41-25, 2nd round exit

2013

The Lakers repeat their 2004 strategy, bringing in Dwight Howard, Steve Nash & Antawn Jamison.  However, the strategy has less success than it did a decade ago as the pieces are brittle and injury prone.  The Lakers finish 40-42 and miss the playoffs.

Actual result:  45-37, 1st round exit

2014

After the "all-in" strategy fails, the Lakers start the tear-down process.  Pau Gasol is now the only link to the past.  However, Jordan makes a surprise return to the team.  There is optimism that the Lakers can have a punchers chance with Jordan & Gasol.  Unfortunately, Jordan is inefficient and ineffective and is a detriment to the team.  The Lakers struggle to a 26-56 record, finishing last in the Division.

Actual result:  27-55, missed playoffs

2015

Gasol leaves, eliminating the one other link to the glory years.  Jordan plays better in his 2nd season of this comeback attempt but the cupboard is completely bare of talent at this point.  The Lakers finish 23-59.  Jordan walks away for good.

Actual result:  21-61, missed playoffs

2016

The Lakers are in full on rebuild mode and go 17-65.  

Actual result:  17-65, missed playoffs

Bryant in Jordan's shoes

Bryant is estimated to achieve almost every accomplishment that Jordan did - at least from a team perspective. Chicago still wins 6 championships and breaks the single season win mark, even if the mark is later broken by Jordan's Lakers.

The projected differences are subtle - Bryant wins 3 fewer playoff series, has one fewer playoff appearance and no longer holds the record for most wins by a championship team.  He doesn't accomplish quite as much as Jordan - but it's very close.  Bryant's teams project to win 36 fewer games over a 20 year run; approximately two fewer wins per year.  The 5-peat over the mid-to-late 90's is the backbone of Bryant's legacy and Bryant is best remembered for sustained greatness.

Jordan in Bryant's shoes

While Jordan doesn't project to capture any incremental titles, he still does achieve slightly more success than Bryant did.  In addition to setting a (seemingly) unbreakable regular season wins record, the Lakers project to win 3 incremental Division titles and 1 extra playoff series win.  It's estimated that the Lakers fail to make 3 playoff appearances, although 3 Division Titles, a record setting season and an extra playoff series win are more valuable.  With 75 wins and a championship, the 2000 Lakers are the consensus greatest team of all time.  

While Bryant's sustained run of excellence is very impressive, Jordan's higher peaks grade out slightly above Bryant.  The Lakers project to generate 24 more wins over a 20 year run with Jordan - about 1 per year.  

Overall, Jordan grades out as being marginally more impactful than Bryant as Jordan's brilliance outshines the extra seasons Bryant provides.