When I released the paperback edition of The Book of Basketball in 2009, I ranked Scottie Pippen 24th all time as a Level Four Hall of Fame Pyramid guy. On my 2020 list, he’s been passed by four players—Kawhi Leonard, Stephen Curry, Dirk Nowitzki and Kevin Durant—landing him at 28th. Here’s what I wrote about Scottie in my book.

24. Scottie Pippen

Résumé: 17 years, 12 quality, 7 All-Stars … Top 5 (’94, ’95, ’96), Top 10 (’92, ’97), top 15 (’93, ’98) … All-Defense (10x, eight 1st) … leader: steals (1x) … 4-year peak: 20-8-6, 49% FG … 4-year playoffs peak: 21-8-6 (61 G) … 2nd-best player on six champs (’91-’93, ’96-’98 Bulls) … ’91 playoffs: 22-9-6 (17 G) … member of ’92 Dream Team … All-Star MVP (1994: 29-11-2, 4 steals)

Some scattered thoughts that will eventually resemble an explanation …

1. The first five Dream Team choices were Jordan/Magic/Bird, then Robinson and Pippen in that order. Those were the five “no-brainers,” according to the committee. From there, they spent the next few weeks choosing a roster that eventually included Barkley, Malone, Stockton, Drexler, Mullin and Ewing (and not Isiah). I don’t know, this seems relevant. Eighteen years later, when I wrote the “Wine Cellar” chapter, my first five choices were Bird, Magic, Jordan, Pippen and McHale. I couldn’t have a Wine Cellar team without those five. From there, I spent the next few days figuring out the other seven spots, changing my mind at least.

2. Of anyone I’ve ever seen in person, Pippen was the best defender. We always hear how Bird and Magic played “free safety,” a nice way of saying that they always guarded the other team’s weakest offensive player, then used that advantage to roam around, sneak behind low-post guys and jump passing lanes. Extending that analogy, Scottie was a strong safety out of the Ronnie Lott mold, a consistently destructive presence who became nearly as enjoyable to watch defensively as Jordan was offensively. Nobody covered more ground or moved faster from point A to point B. It was like watching a cheetah in a wildlife special—one second Scottie would be minding his own business, the next second he would be pouncing. Everyone remembers Kerr’s jumper to win the ’97 Finals, but nobody remembers Pippen tipping Utah’s ensuing inbounds pass, then chasing it down and flipping it to Toni Kukoc to clinch the game. No other player except for Jordan, LeBron and maybe Kobe had the physical gifts and instincts to make that play.



3. Only Jordan was a better all-around player in the ’90s … and that was debatable. From ’91 to ’95, Pippen averaged a 20-8-6 with 2.4 steals, shot 50 percent and doubled as the league’s top defensive player. In the playoffs from ’91 to ’98, he averaged 17-23 points, 7-9 boards and 4-7 assists every spring and consistently defended the other team’s best scorer. During MJ’s “sabbatical,” Scottie (20.8 PPG, 8.7 RPG, 5.6 APG, 49% FG) dragged the Bulls to within one fecally pungent call of the Eastern finals and should have been our ’94 MVP runner-up behind Hakeem. The following year, he became one of four postmerger players (along with Cowens in ’78, Kevin Garnett in ’03 and LeBron in ’09) to lead his team in total points, rebounds, assists, steals and blocks in the same season. And he redefined the “point forward” concept during the ’90s, allowing the Bulls to play any combination of guards without suffering in the ballhandling/defense departments.

Chuck Daly created a great term to describe Scottie: a “fill in the blanks” guy. If a teammate was getting killed defensively, Scottie had his back. If you needed rebounding, Scottie went down low and grabbed some boards. If you needed scoring, Scottie could create a shot or attack the rim. If you needed a turnover, Scottie had a better chance of getting it than anyone. If you needed ballhandling, he could do it. And if you needed to shut someone down, he did it. Like the Wolf in Pulp Fiction, Scottie specialized in cleaning up everyone else’s mess. When Magic was running amok in the ’91 Finals, Scottie put the clamps on him. When the Knicks were shoving an MJ-less Chicago team around in the ’94 playoffs, Scottie dunked on Ewing and stood over him defiantly. During the Charles Smith Game the year before, Pippen and Horace Grant were the ones stuffing Smith and saving the series. When the ’98 Pacers nearly snuffed out the MJ era, Jordan and Pippen crashed the boards in Game 7 and willed themselves to the line again and again, two smaller guys dominating the paint against a bigger team. They just wanted it more.



4. During the Dream Team practices, Daly called Scottie his second-best player and told David Halberstam, “You never really know how good a player is until you coach him, but Pippen was a great surprise in Barcelona—the confidence with which he played and the absolutely complete nature of his game, both on offense and defense. No one else really expected it.”

According to Halberstam, MJ returned to Chicago after the Olympics and told Phil Jackson, “Scottie came in as just one of the other players, and none of the others knew how good he was, but then he kept playing, and by the end of the week it was clear that he was the top guard there—over Clyde and Magic and Stockton. It was great for people to see him in that setting and see how good he really was.” For those of you scoring at home, that’s 16 combined rings paying homage.

5. Irrefutable fact: Jordan never would have retired in ’99 unless he knew for sure that Scottie was leaving. You think Crockett was trying to win a seventh title without Tubbs? No way. I always liked the Miami Vice analogy for them: Crockett got most of the attention and deservedly so … but he still wasn’t taking Calderone down without Tubbs. You could also rely on Tubbs/Pippen to carry their own episodes every now and then, although Tubbs never could have carried a whole season of Vice like Pippen carried that ’94 Bulls team. His detractors conveniently forget that season, just like they ignore Older Scottie leading Portland to within one self-destructive quarter of the 2000 Finals, or how he jeopardized his impending free agency in the ’98 playoffs by gutting it out with a herniated disc, even limping around in Game 6 of the Finals just because the Bulls needed his presence.

If you’re poking holes, you can easily dismiss him as Jordan’s sidekick, or mention his infamous migraine before Game 7 of the ’90 Pistons series (which happened only a few days after his father passed away, but whatever). “Hey, if all else fails and you want to discredit Pippen, just bring up the quitter thing.”

And so where you stand on Scottie depends on one question: Do you give up on anyone who ever made a stupid mistake?

We all remember that fateful ’94 Knicks series, when Scottie refused to finish Game 3 because Phil Jackson called the final play for Kukoc (who swished the game-winner with Pippen sulking on the bench). A betrayed Bill Cartwright screamed at Pippen afterward with tears rolling down his face, later calling it the biggest disappointment of his career. And maybe it was.

Of course, Scottie carried a Jordan-less Bulls squad to 55 wins by himself. It had become his team, and when it’s your team, a mind-set takes hold: Everything rests on your shoulders, everyone is gunning for you and you can’t take a night off. You become the pumped-up star of your own action movie. Unless you think like a superhero, you won’t survive. Scottie wasn’t wired that way, so he had to play the role of the alpha dog … and Game 3 was his Jimmy Chitwood moment. He’d earned the right to say, “Coach, I’ll make it.”

Jackson took the moment away and gave it to Kukoc, a slap in the face if you understood Scottie’s back story. He hailed from a dirt-poor town in Arkansas, one of 12 siblings with an ailing father who couldn’t work anymore. After an improbable growth spurt propelled him to NAIA Division I stardom, Scottie’s stock skyrocketed right before the ’87 draft, which pretty much invented NBA draft code words like “upside,” “length” and “wingspan.” Chicago flipped top-eight lottery picks with Seattle, then locked Scottie up with a six-year deal (eventually tacking on a five-year extension that became a bigger bargain).

So when the Bulls courted Kukoc for most of Scottie’s career, Scottie never forgave them for it. Or Kukoc, for that matter. Had Scottie played out that rookie contract and become a free agent in ’93, right as Jordan was retiring, his value would have soared. (For the first 11 years of his career, Scottie Pippen was woefully underpaid. He was the 122nd-highest-paid player in the NBA in 1998.) That’s what led to the regrettable decision in the Kukoc game: a Molotov cocktail of money, jealousy, insecurity, ego and competitiveness exploded at the worst possible time. Scottie apologized, his team forgave him, he took the heat and that was that. Shit happens. The Bulls won three more rings with him. Everyone forgets that part. If you think one selfish moment should overshadow a totally unselfish career, maybe you should climb off your high horse before you get hurt.



Scottie finally fetched his mammoth payday after the ’99 lockout, leading to a basketball purist’s tragedy: Scottie toiling away for one Rockets season in a stilted, slow-it-down “Hey, Scottie, dump it into Hakeem or Barkley, go to the corner and stand there” offense. Almost as bad as seeing Jason Kidd in the triangle. Pippen finally escaped Jordan’s shadow in Portland, where he led a dysfunctional Blazers team to the precipice of the 2000 Finals—15-point lead, 10 minutes to play—before everything fell apart in a quagmire of improbable 3s, shaky calls and bad coaching.

Critics pointed to that game as more evidence that Scottie couldn’t be the best guy on a championship team. Good, that puts him with these guys: Cousy, Malone, LeBron, Barkley, Garnett, McHale, Gervin, Oscar, Kobe, Robinson, Ewing and Baylor. I hope history remembers him as an exceptional athlete who redefined his position, routinely played hurt, allowed Jordan to blossom into “best player ever” status and ended up with enough rings for two hands.

Every time I tried to talk myself out of putting Pippen in the top 25, I kept thinking about the time Chicago’s soon-to-be-legendary ’96 team cruised through Boston right before Christmas. They were 19-2, working on a 10-game winning streak and generating the first wave of “greatest team ever” buzz, a complete affront to everyone who loved the ’86 Celtics in Boston. Come on, they couldn’t be that good, right?

Then Jordan and Pippen came out and whupped our crummy team for two-plus hours. This was like watching Andre the Giant in his prime, when he’d come out smiling for a battle royal as the crowd went bonkers, then disdainfully tossed jabronies out of the ring for the next 20 minutes. By the fourth quarter, two-thirds of the crowd was rooting for Chicago under the rarely seen and entirely defensible “not only is our team reprehensible, but we used to root for a great team, we know greatness, we understand greatness and this is greatness” corollary. Jordan and Pippen finished with 37 points apiece. Scottie chipped in 12 assists and nine rebounds for good measure. Then they flew to the next city and kicked the shit out of somebody else. Don’t tell me that Scottie Pippen wasn’t great.

Bill Simmons’s The Book of Basketball: The NBA According to The Sports Guy was published in 2009 by ESPN Books. Read it now. The 2019-20 podcast sequel, The Book of Basketball 2.0, is available to listen to now.