He’s arguably the best “Robin” in NBA history. A Hall of Famer, a six-time NBA champion, a seven-time All-NBA team member, a seven-time All-Star, and a two-time member of the NBA Anniversary team.
Yet, believe it or not, at one point in his basketball career, Scotty (Scottie) Maurice Pippen Sr. was considered an underdog to even play college basketball.
To fully understand how unlikely it was for Pippen to make it to the biggest basketball stage in the world, you have to first look at where he came from.
Born on September 25th, 1965, in Hamburg, Arkansas, Scottie was the youngest of Preston and Ethal Pippen’s twelve children.
Coming from a working-class family in rural Arkansas, not exactly known as a hotbed for hoops, Pippen faced some issues growing up that many of his peers did not.
At the age of 8, Pippen’s second-oldest brother became paralyzed following an injury in gym class, a situation that impacted the family’s finances.
Unfortunately, Pippen’s family health issues worsened years later when his dad, who worked at the local paper mill, suffered a stroke when Scottie was just fourteen years old, resulting in the loss of his job.
Whereas others were going to expensive basketball camps or joining AAU teams, the Pippen family could not afford the extras.
Despite all the issues at home, Scottie managed to remain focused at school, leading the Hamburg Lions to the state regional playoffs while earning All-Conference honors.
Yet not one school offered him the opportunity to continue playing past high school.
A lanky, 6’1”, 150lb point guard, Scottie played for Donald Wayne, a longtime coach at Hamburg High School. A former college player at Henderson State, Wayne saw something in Pippen that others did not.
“Having played point guard myself in college, I saw some traits in him that made me believe he could play at that level. Scottie could handle the ball and shoot it well. He ran our offense very well and didn’t take bad shots. He was a pretty decent-sized point guard for back then in high school, but had he grown earlier, I think he may have gotten some more attention.”
Thankfully, Wayne was still in touch with his former coach, Don Dyer, who had become the coach at the University of Central Arkansas.
A small NAIA school, the Bears weren’t exactly a powerhouse college basketball program. And yet, the only opportunity that Pippen was given during his freshman year was to come in as a walk-on.
With no scholarship money available and financial issues at home, he doubled as the team’s equipment manager, earning financial aid to help pay his tuition.
As a walk-on, Scottie didn’t expect to play at all as a freshman. But after several players left the team, he ended up playing 20 games – averaging just 4.3 points, 3 rebounds, and less than an assist per game.
“Every other player on the floor was on scholarship except me,” he wrote in his book, Unguarded.
“No problem, I told myself. I would wait for my turn.”
By the start of his sophomore year, he’d grown another five inches and packed on some muscle.
“A few guys academically fall off, so some scholarships [become] available,” Pippen said in The Last Dance. “I go back, ask the coach. I was very persistent, and he finally gave me a scholarship.”
Having put in the extra hours of work on the court as a freshman in hopes of seeing some court time, Pippen became the leader of the Bears in his second season, averaging a team-high 18.5 points, 9.2 rebounds, and 1.6 assists.
During the summer, he stayed in his college town of Conway to work the graveyard shift at a welding plant that built office furniture.
While the work was dangerous – and at times, life-threatening – Scottie said the paycheck made it worthwhile.
“I earned about $750 a week, saving close to $5,000 that first summer. To someone from my background, it was like winning the lottery.”
After work, he’d drive home for a short workout and then go play for a summer league team.
Those hours paid off and took his game to another level. At one point, he considered transferring to a bigger school.
“I was a Division I talent trapped in what was, essentially, a Division II school, afraid I would never be discovered. This was long before the internet.”
But his coach convinced him to stick around, assuring him that he’d call scouts and make sure people would find him.
“Coach J sincerely believed I would be happier in Conway, and in the end, he was right.”
During his third college season, he earned a spot on the NAIA All-American Team.
Standing 6’7” by the time his senior year tipped off, Pippen posted a career high stat line of 23.6 points, 10 rebounds, 4.3 assists, and 3.1 steals with a shooting percentage split of 59.2/57.5/71.9.
Once again, a member of the NAIA All-American Team, Pippen had turned himself from a kid who couldn’t get a scholarship from a major college into a legitimate NBA prospect.
When the 1987 NBA Draft rolled around, Scottie was selected before household names like Kenny Smith, Kevin Johnson, Reggie Miller, Mark Jackson, and Reggie Lewis – players who had a much larger amateur pedigree.
Drafted fifth overall by the Seattle Supersonics, even commissioner David Stern was a bit thrown off, announcing him as “Scott Pippen”.
However, his time as a Supersonic was just a formality as Chicago Bulls GM Jerry Krause had worked out a deal to swap Olden Polynice, a 1998 second-round pick, and a 1989 first-round pick swap for Pippen.
While Scottie had an impressive offensive stat line during his final college season, that wasn’t what attracted Krause to make the deal.
“What I saw in Pippen was a chance to be a great defensive player,” Krause said.
“I saw a guy with long arms and quick feet and big hands and all the things — who couldn’t shoot. He was not a good shooter. Now, when I first saw Michael Jordan, he wasn’t a good shooter either. Shooting can be improved. It’s a skill that can be worked at. What I saw in Pippen was a guy that could guard ones, twos, threes, and fours, and I fell in love with that.”
Coming off the bench during his first season, like many rookies, he had his highs and lows, averaging 20 minutes per game with 7.9 points, 3.8 rebounds, 2.1 assists, and 1.2 steals.
While he filled the stat sheet, it wasn’t with numbers worthy of a high draft pick, especially when names like Greg Anderson and Winston Garland finished tied for second in the Rookie of the Year race.
Many thought Krause made a huge mistake.
By the time his third NBA season came about, Pippen had earned the starting small forward position with the Bulls, thanks to his continued hard work, grit, and perseverance, and maybe putting in extra practice with a guy named Michael Jordan.
It’s no coincidence that with his growth both offensively and defensively, he became an All-Star and helped the Bulls become serious contenders in the Eastern Conference.
Playing on a 4-year, $2.83 million rookie contract, Pippen had more than earned his pay, money that was more than he had ever expected to make growing up in Hamburg.
During the 1989 and 1990 playoffs, the Bulls found themselves facing the Detroit Pistons, dubbed the “Bad Boyz” for their physical defensive style of play that bordered on malicious.
In Game 7 of the 1990 Eastern Conference Finals, he dealt with a debilitating migraine headache that left him a shell of himself.
In 42 minutes of game time, he went 1-10, finishing with 2 points and 4 rebounds. Many thought that he wasn’t ready for the big stage.
“He’s the guy that can be shaken,” Jordan said about Pippen being regarded by opposing teams as a soft player.
But everything came together for Scottie and the Bulls during the 1990-91 season.
Finishing with a 61-21 regular season record, Chicago suffered just one playoff loss en route to a matchup with the LA Lakers in the NBA Finals. While all eyes were rightfully on Jordan and Lakers legend Magic Johnson, it was Pippen who stole the show, playing lockdown defense on the Lakers’ point guard throughout the five-game series.
Whereas a year earlier, he’d been criticized for his inability to show up in the big moment, Pippen capped off the Bulls’ 4-1 series victory with a game-high 32 points.
With his contract at an end, coming off one of the most important victories of his basketball career, one that cemented him as a championship-caliber player, Scottie once again found himself undervalued for his talents.
Presented with a 7-year, $18 million contract, he signed his name on the dotted line, knowing that he could take care of his entire family. While $2.57 million per year wasn’t terrible to start, it quickly became one of the most grossly underpaid deals in sports history.
As players’ salaries began to skyrocket during the 1990s, Pippen’s deal became laughable.
Turning himself into arguably the best two-way player in the league at the time (not named Jordan), Pippen was an MVP candidate and six-time NBA Champion by the end of the 1997-98 season.
Yet throughout that period, he was often not paid like the second-best player on his own team, and at one point was the 122nd highest paid player in the league. A blatant slap in the face.
But it wasn’t just the money, or lack of it, that Pippen had to deal with as a member of the Bulls. There was also the constant disrespect from the front office itself.
In 1990, Chicago drafted Toni Kukoc, and when the Croatian star finally joined the team in 1993, the team had used $2 million of the money they could have offered to Pippen to pay for Kukoc.
This wouldn’t be the only issue that Pippen had with Kukoc, who was famously given the last shot opportunity during the 1994 Eastern Conference Finals. Believing he had rightfully taken over the throne when Jordan left the NBA to play baseball, it was clear the Bulls thought otherwise.
“I wasn’t thrilled, however, with another move the Bulls made, which was signing Toni to a new deal for $26 million over six years, the largest in the history of the franchise,” Pippen noted in his book Unguarded.
“It figured. They leave me underpaid year after year, then hand Toni a fortune. First the last shot and now this.”
Then there was the proposed trade to Seattle for Shawn Kemp in 1994 that was only called off because of the Sonics’ owner.
The next season, the Bulls brought in Pippen’s biggest rival, former Pistons forward Dennis Rodman. Two years later, Pippen was almost traded for high school star Tracy McGrady.
How could someone who brought so much success to a franchise be treated with so little appreciation?
Although he was underpaid and underappreciated, Pippen continued to show up night after night, season after season, for a team that clearly benefited from his talents.
He was eventually moved prior to the strike-shortened 1998-1999 season in a sign-and-trade deal with the Houston Rockets, and would go on to play four years with the Portland Trail Blazers, before returning to the Windy City for his final NBA season in 2003-04.
Yes, he made significantly more money during his five seasons outside of a Bulls uniform. But it was his humility, gratitude, willingness to work hard, and accept less to be part of something great that many will remember about Pippen’s journey from being a teenage afterthought into one of the greatest NBA players of all time.
“Everything was a lesson learned and a step forward for me.”
