Who Would Win If Prime Jordan, Scottie And Olajuwon Battled Kobe, LeBron And Shaq?

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A musty, sweltering gym. Air thick with the smell of sweat. One ball bouncing like a pulse, with the squeaks of sneakers filling in the spaces in between. Six men, two teams of three, warring mercilessly against each other.

Kobe Bryant fires a bullet pass over Michael Jordan’s outstretched hand to LeBron James, who is cutting across the free throw line with Scottie Pippen riding his hip. LeBron catches the ball and lobs a no-look touch-pass high above the rim, where Shaq out-jumps Hakeem Olajuwon and throws it down with one hand. Just like he did against Portland in the playoffs in Game 7 of the 2000 Western Conference finals, King James knows his YouTube clips.

There is no celebration; Jordan is already taking the ball out up top. Pippen clears out, dragging LeBron with him, and Jordan looks to feed Hakeem on the right block. The Dream Shake is coming.

Part of being an NBA fan is all the hypothetical matchups.

Perhaps more than any other sport, the NBA lends itself to arguments of the imagination. What would have happened if the ’96 Bulls had played the ’01 Lakers? Would the original Bad Boys have beaten the 2004 reincarnation? (Laimbeer versus Sheed, forever, yes please, thank you.)

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These hypothetical matchups are at once maddening and fun, because you can’t really prove or disprove them. For every serious discussion comparing the 1980s Celtics and Lakers or the 2010s Heat and Spurs, there are a dozen hypothetical matchups between teams who never played each other. And if two teams never played each other, you can’t be wrong when you pick one. This frees you up to plant your flag on some lonely hilltop where no one will join you, and you can feel special and unique when you drop your hot take about how the 1983 Sixers were the GOAT (for the record, I am 100 percent behind that hot take).

So let’s do one together. Quite simply, if there was a 3-on-3 game and all of the players were at their professional peak, which of these teams would win?

Michael Jordan, Scottie Pippen, and Hakeem Olajuwon

OR

Kobe Bryant, LeBron James, and Shaq

Most people immediately — almost instinctively — leap to one side. But if you stare at the teams for a moment and start to dig through the layers…it goes deep, man. You fall into the rabbit hole and don’t come out.

Thankfully this is the internet, where no one ever gets upset and disagrees, so let’s go in together:

What kind of 3-on-3 game are we talking bout?

Halfcourt, by 2s and 3s. We need to keep the game moving, so it will be loser’s out and timed. A typical NBA starter shift is about 8-12 minutes, so let’s say four, 8-minute quarters. A referee calling fouls — no ticky-tack stuff, but keeping firm control. No limit to fouls, but there are also no free throws; after the fifth foul in a quarter, you get one point plus possession.

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The Matchups

Jordan and Kobe guard each other
Pippen and LeBron guard each other
Hakeem and Shaq guard each other

The Case For Team ’90s [Jordan/Pippen/Hakeem]

-Michael Jordan. He defeated the Monstars. He was pretty good.

-Defense. Jordan and Pippen were the best tandem of wing defenders ever. They hounded the ball, rebounded above their positions, and generally created havoc for the other team. Add to this Olajuwon — the best defensive center since Bill Russell — and you have a pretty airtight defensive unit.

Now, that being said, peak Hakeem ain’t stopping peak Shaq. There is not a center dead or alive who could have stopped peak Shaq once he caught the ball in his scoring area.

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But what about the argument “Dream beat Shaq in ’95?” Well, that’s not entirely fair. That was young Shaq. Sometimes great players lose Finals when they are young. Hakeem lost in 1986, and no one holds that against him to somehow rank him under Robert Parish in the center pantheon.
So yes, Shaq is going to throw a few down in the Dream’s grill. That being said, Hakeem’s defense still changes the equation. He is fleet-footed enough to show on pick and rolls, and this will keep Kobe and LeBron from easily turning the corner off screens. Shaq will not do this; he will sink back into the lane on defense, where he’s a lesser shot blocker than Dream anyway. Advantage Team ’90s.

The Case for Team ’00s [Kobe/LeBron/Shaq]

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-Sheer talent. Whereas Team ’90s has better chemistry, Team ’00s is more gifted. They are also bigger and stronger. Shaq is much more powerful than Olajuwon. Pippen, for all his defensive ability, is still giving up weight and strength to LeBron. Strength matters. It will matter when Shaq cannot be dislodged from the post. It will matter when LeBron absorbs Pippen’s contact and finishes anyway.

-It’s not like Jordan couldn’t be beaten:

-Also, Nick Anderson.

So Who Wins?

I have no clue! Let’s walk through this together.

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It will take Team ’90s about 0.00007 seconds to figure out that LeBron doesn’t like it when someone talks junk to him on the court. He’s the King, right, and no one challenges the King. So Team ’90s will call him words that rhyme with “ditch,” “fussy,” and “maggot,” because in the ’90s those were words you could use without getting a call from the league office in the morning and having your publicist tweet an apology from your Twitter account.

So maybe LeBron gets off his game at first. And if this was 2010 Emo Kylo Ren LeBron, maybe he stays in a funk. But this is Peak LeBron, 2013 Killing the Spurs in Game 7 LeBron. He’s not going to pout; he’s going to mash that Beast Mode button and do one of those I DARE YOU TO GET IN FRONT OF ME drives down the lane. He drives, gives Pippen a little Byron Russell shove, scores a layup, then turns to give Jordan a glare. MJ smirks.

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The mind games from Team ’90s continue: Pippen is in Kobe’s ear, goading him that Jordan, his idol, is better. Now Jordan is taunting Kobe, saying the same thing; Challenging him. Team ’90s is devious; they are baiting Kobe into hero ball, into launching a Captain Ahab quest to finally beat Jordan.

It works: Kobe looks off Shaq in the post and fires a long fadeaway that clanks off the rim and is gobbled up by Olajuwon.

Now Shaq is angry and woofing at his teammate. Shaq and Kobe may be at their physical peak, but their chemistry is devolving into 2004 all over again. Olajuwon sets a pick on Kobe, and Shaq neither calls it out nor hedges. Jordan dribbles around Shaq and reaches under the rim for a reverse layup. LeBron saw it coming; he abandons Pippen on the weak side and dives back into the paint to swat the ball away. MJ and LBJ go toe to toe under the rim and the ref has to separate them. LeBron doesn’t say a word and Jordan is just smacking that gum, sweat pouring off his forehead, wheels spinning, planning his next move.

Now Pippen wants the ball at the elbow. Jordan gives it up and fades to the corner, jawing the entire way at Kobe, who follows him.

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Pippen calls Hakeem to set a screen. This time, Shaq lumbers forward, intent on hedging and recovering. However, Olajuwon is a step ahead; he slips the screen and dives back to the rim, changing directions faster than the heavier Shaq can follow. Pippen lobs a perfect pass from the elbow that Hakeem catches and finishes in one elegant motion.

And now Shaq is nodding, yelling at LeBron to feed him on the next possession because it’s his turn. And Jordan is cackling, and Kobe is blowing into his hands and making the Underbite Face. And Pippen just teased LeBron about losing in three Finals and LeBron loudly brought up when Pippen said LeBron was better than Jordan. And Hakeem is just smiling, somehow above the fray, strangely serene for a man who’s about to feel 330 pounds of center crash into him.

Hakeem Olajuwon, Shaquille O'Neal
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Who wins this game? If they played 10 times, I would guess that Team ’90s wins four and Team ’00s wins six. But one game, for bragging rights? That might be different. Do you want to bet against Jordan? Or do you trust LeBron’s talent?

You tell us. Who wins?

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