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Home > NBA News & Analysis > Scottie Pippen Would’ve Won 10 NBA Championships If He Joined The Lakers In 1999

Scottie Pippen Would’ve Won 10 NBA Championships If He Joined The Lakers In 1999

Scottie Pippen would've made one of the best decisions in NBA history if he joined the Los Angeles Lakers.

Eddie Bitar
Apr 3, 2023
15 Min Read
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Credit: Fadeaway World

Scottie Pippen is one of the top 50 NBA players in NBA history. What he accomplished alongside Michael Jordan was legendary because they won six NBA championships together and built a dynasty that changed the league forever. More specifically, Pippen and Jordan formed arguably the greatest duo in the history of basketball because they never lost in the NBA Finals together.

Contents
  • A One-Year Stint In Houston That Eventually Involved Scottie Being  Sent To Portland
  • Scottie Pippen Traded To Los Angeles Instead Of Portland In A Trade Involving Glen Rice
  • Los Angeles Lakers Go 4-1 In NBA Finals Between 2000 And 2004 With Scottie Pippen
  • Scottie Pippen’s Legacy Changes Forever, Along With Altered History
    • Next
    • Ranking The Top 10 Best Duos In NBA History
    • 10 Greatest Chicago Bulls Players Of All Time
    • 25 Greatest NBA Players And Their Best Teammates

When looking at Pippen’s accomplishments, it is clear as day that he was a first-ballot Hall of Famer. The small forward won six titles, made seven All-Star Teams, seven All-NBA Teams, and 10 All-Defensive Teams. Pippen was also the 1994 All-Star MVP and unsurprisingly retired as a Hall of Famer as one of the greatest defensive players of all time. Somehow, Scottie Pippen was disrespected throughout his career and still gets the short end of the stick until this day.

Obviously, playing alongside the greatest figure in the history of team sports will tend to underrate anyone around him, and Pippen was a victim of that. No matter what, Pippen managed six NBA titles and would have had 10 NBA championships had his career gone a little differently. Here is how this would have been possible if Scottie Pippen had joined the Los Angeles Lakers instead of being traded by the Houston Rockets to the Portland Trail Blazers. Scottie Pippen started this conversation himself when he claimed what would have happened if he had teamed up with a prime Shaquille O’Neal.

Scottie is clearly intrigued about how his future would have changed if he played with the Lakers, and it would have completely altered the player’s reputation and career. Let’s go back in time and benefit Scottie Pippen’s career far more by re-writing how his career ended. Here is a hint: Scottie Pippen would probably be in the conversation for being a top-10 player of all time.


A One-Year Stint In Houston That Eventually Involved Scottie Being  Sent To Portland

Upon Michael Jordan’s second retirement, Scottie Pippen requested a trade and was sent to the Houston Rockets. Pippen’s decision to get traded was largely financially based because Scottie was one of the most underpaid players of all time. The Rockets acquired the 6-time NBA champion and All-Star forward for a negligible package that was simply higher in the salary offered to Pippen. Rather than sign a four-year, $45 million deal with a new team, Pippen signed a five-year, $67 million deal with the Bulls before being traded to the Rockets. The Rockets gave up bench player Roy Rogers and a second-round pick, so that was a steal for Houston.

The Rockets already had two-time NBA champion and Finals MVP Hakeem Olajuwon on the roster, but adding one of the greatest forwards of all time to form a dynamic defensive duo made a ton of sense. Charles Barkley was also on the team, and even at 35 years old, he was still a factor. On paper, the Rockets looked like a very solid team that could challenge for the NBA championship, but the way it played out was much different. The Rockets finished with a 31-19 record in the lockout-shortened season. The lockout lasted from July 1, 1998, to January 20, 1999, which meant the All-Star Game was canceled.

Houston finished 4th in the Western Conference, 6.0 games behind the San Antonio Spurs in the first spot. In the postseason, it was even worse as the Rockets lost to the Los Angeles Lakers in four games (3-1). Hakeem Olajuwon (36), Scottie Pippen (33), and Charles Barkley (35) were far past their primes, and it was clear that competing for an NBA title was not going to work with the old guys. After one year, the Rockets decided to trade Scottie Pippen to the Portland Trail Blazers on October 2nd, 1999. The Portland Trail Blazers traded Stacey Augmon, Kelvin Cato, Walt Williams, Brian Shaw, Ed Gray, and Carlos Rogers to the Houston Rockets for Scottie Pippen.

That move ended up being the final real move by Pippen to give him a chance for a title, and the player led the team to the Western Conference Finals in 2000 in a loss to the Los Angeles Lakers. The following year, the Trail Blazers were swept by the Lakers in the first round. In 2002, the Trail Blazers were swept by the Lakers a second time before losing in seven games to the Dallas Mavericks in the first round in 2003. Pippen played one final season in 2004 with the Chicago Bulls, but he only averaged 5.9 PPG in the season and missed the playoffs with a 23-win team.

Scottie Pippen would have won 10 NBA championships had he never been traded to the Portland Trail Blazers and instead traded to the Los Angeles Lakers team that had Shaquille O’Neal and Kobe Bryant.


Scottie Pippen Traded To Los Angeles Instead Of Portland In A Trade Involving Glen Rice

Scottie Pippen would have been in a far better situation if he had joined the Los Angeles Lakers instead of the Portland Trail Blazers. The Lakers team was already stacked, but acquiring Pippen would have lifted the team to another level. Glen Rice, the Lakers’ sharpshooter who posted 17.5 PPG in the 1999 season, would have been included in the trade to Houston along with two first-round picks for Scottie Pippen.

Trade Package: Glen Rice, Two First-Round Picks for Scottie Pippen

The Rockets would have replaced Pippen with a better shooter in Rice to pair with Hakeem and Barkley, and the Lakers would have been even better. How would the Lakers line up with Pippen on the team to form a Big Three? Just look at their depth chart.

Starting Lineup: Ron Harper, Kobe Bryant, Scottie Pippen, A.C. Green, Shaquille O’Neal

Bench: Derek Fisher, Tyronn Lue, Brian Shaw, Rick Fox, Devean George, Robert Horry, John Salley, Mark Madsen

Pippen slides in the perimeter alongside Kobe Bryant and a guard rotation of Ron Harper or Derek Fisher. With the big man Shaq down low, the Lakers would have the best team in the NBA by a wide margin. Losing Glen Rice is not ideal, and neither are two first-round picks, but Los Angeles was in purely contention mode with Phil Jackson at the helm, and nothing mattered except winning rings.

Of course, Scottie Pippen would be reunited with his old Chicago Bulls coach, Phil Jackson, and the legendary mastermind would have found a way to incorporate an older and stubborn-headed Pippen who wants to prove he can win without Michael Jordan. Scottie was still an elite defender at 34 years old and could still bring championship experience along with excellent playmaking ability. As the third option on the team behind Shaq and Kobe, Pippen would have fit in perfectly, and the Lakers would have won four NBA titles over the next five years, taking Pippen’s championship tally to a whopping 10.


Los Angeles Lakers Go 4-1 In NBA Finals Between 2000 And 2004 With Scottie Pippen

The Los Angeles Lakers between the 2000 and 2004 seasons were absolutely dominant. They won three NBA championships in four Finals appearances over that span, a shockingly great run. With Pippen, the Lakers repeat the same championships they won in 2000, 2001, and 2002. In 2000, the Lakers went up against the Indiana Pacers led by Reggie Miller, and the Pacers had no answer for Shaq. Instead of a 6-game victory, Pippen probably makes it a shorter series into 5 games. Remember, Pippen was part of the Portland Trail Blazers squad that pushed the Lakers to 7 games, so not having him in Portland would have meant the Lakers cakewalked to the Finals.

In 2001, the Lakers went up against the Philadelphia 76ers, led by MVP Allen Iverson. Iverson had the heart to win Game 1, but that was all he could do as the Lakers took them apart. A 34-year-old Dikembe Mutombo could not stop a prime Shaq, and the series ended in five games. Again, with Pippen, it is probably a game shorter, which means the Lakers win in a sweep, with Pippen defending Iverson for most of the game.

In 2002, the Lakers swept the Jason Kidd-led New Jersey Nets, and with Pippen on board, it is probably the same. Essentially, Pippen would only make the Lakers more dominant over their 3-peat, and the forward would have had nine NBA championships through three separate 3-peats. Simply extraordinary. What about the 2003 and 2004 seasons?

It is likely that Scottie Pippen would have helped the Lakers reach the Western Conference Finals in 2003, but the team would not have defeated the San Antonio Spurs. The Spurs ended up winning the NBA title in actuality, thanks to the superstar dominance of Tim Duncan and the supporting cast of Tony Parker, Manu Ginobili, and David Robinson. It is easy to assume that the Lakers win the series, but considering how dominant Duncan was all year as he won the MVP award, the Lakers would have not made the Finals even with Pippen.

With Pippen, the Lakers end up winning the 2004 NBA championship over the Detroit Pistons. The Pistons somehow defeated the Lakers in five games in actuality when the Purple and Gold had Karl Malone and Gary Payton, but both were very past their prime. Scottie would retire following the 2004 Finals, but he would have made enough of an impact with his championship experience to make a difference. With Pippen acting as a buffer between Shaq and Kobe, the Lakers would have focused enough to win the title against the inferior Pistons squad.


Scottie Pippen’s Legacy Changes Forever, Along With Altered History

Had Scottie Pippen been traded to the Los Angeles Lakers instead of the Portland Trail Blazers, the forward would have had 10 NBA titles on his resume while Shaq and Kobe earn an extra championship ring. How would NBA history look different if Kobe had six rings and O’Neal had five? For one, Bryant would be more involved in the GOAT debate as the only man to mimic Michael Jordan and have the same number of rings. O’Neal would have also surpassed every center as the greatest big man ever, possibly usurping Kareem Abdul-Jabbar as well.

Most importantly, Scottie Pippen would probably be remembered as a top-ten player of all time. Pippen would have had 10 NBA championships and a 10-0 Finals record, along with his individual accolades (seven All-Star appearances and 10 All-Defensive Team selections). Would the Pippen disrespect continue? Absolutely not.

Pippen would no longer be looked at as Michael Jordan’s “Robin” but as a player who managed to be involved in three separate 3-peats and capture 10 rings in flawless fashion. Only Bill Russell would have more NBA titles, and Pippen would likely be among the top-ten players ever for most people because his Finals success would be hard to ignore. Instead, Pippen occupies a ranking somewhere in the top 30 and is often mentioned behind Michael Jordan in every conversation. Had Scottie been traded to the Lakers instead of the Trail Blazers, the entire course of NBA history might have changed for one of the greatest small forwards ever in Scottie Pippen. Move over Larry Bird, Scottie would have been the best wing player of his generation. 

Next

Ranking The Top 10 Best Duos In NBA History

10 Greatest Chicago Bulls Players Of All Time

25 Greatest NBA Players And Their Best Teammates

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TAGGED:Kobe BryantLos Angeles Lakers ArchiveScottie PippenShaquille O'Neal
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ByEddie Bitar
Eddie Bitar is a senior staff writer for Fadeaway World from Denver, Colorado. Since joining the team in 2017, Eddie has applied his academic background in economics and finance to enhance his sports journalism. Graduating with a Bachelor's degree from and later a Master's degree in Finance from Utrecht in 2018, he integrates statistical analysis into his articles. This unique approach provides readers with a deeper understanding of basketball through the lens of financial and economic concepts.Eddie's work has not only been a staple at Fadeaway World but has also been featured in prominent publications such as Sports Illustrated. His ability to break down complex data and present it in an accessible way creates an engaging and informative way to visualize both individual and team statistics. From finding the top 3 point shooters of every NBA franchise to ranking players by cost per point, Eddie is constantly finding new angles to use historical data that other NBA analysts may be overlooking.A lifelong basketball fan, Eddie grew up trying to mimic Jason Kidd's game. When asked which NBA player, past or present, he would most like to interview, Eddie's choice is clear: Jason Kidd. He admires Kidd's genius at playing point guard and his ability to lead a team to two NBA Finals appearances. Eddie believes Kidd is an underrated star who deserves more praise, and he would relish the opportunity to pick his brain and discuss the intricacies of the game.
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