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When the NBA lockout happened in 1998 and lasted up until January of 1999, no one knew if the Chicago Bulls would be able to make another run after their “Last Dance” championship run in 1998. One key figure in Chicago’s dynasty was Scottie Pippen who had been in a toxic relationship with Bulls management. Longing for a new contract, Pippen finally got his wish, but on a new team. 

Soon after the lockout ended, the Bulls signed Pippen to a five-year, $67 million deal and subsequently dealt their perennial All-Star forward to the Houston Rockets in a sign-and-trade deal for big man Roy Rogers.

Pippen essentially replaced the recently retired Clyde Drexler in Houston’s veteran trio with Charles Barkley and Hakeem Olajuwon. A free agent at the same time, Barkley took a pay-cut so the Rockets could acquire Pippen. With rookies Michael Dickerson and Cuttino Mobley in the backcourt along with Pippen, Olajuwon and Barkley, the Rockets had a new-look team.

Houston won five of their first six games during the 1998-99 season, but was inconsistent throughout. A nine-game winning streak in late-March got the Rockets to 22-9 and third in the West. However, Houston faltered down the stretch going 9-10 to finish 31-19 and in fifth place due to a tiebreaker loss to the Los Angeles Lakers.

Pippen was slow to adjust to Houston’s offense, posting 14.9 PPG, his lowest scoring average since his second season in the league. Pippen also managed 6.5 RPG, 5.9 APG, 2.0 SPG and 0.7 BPG in 50 games and 40.2 MPG. He also shot 43.2% from the field, the lowest shooting percentage of his career up until that point. 

Houston’s offense was built around post-ups for Olajuwon and Barkley. The Rockets’ goal was to force the opposition to double team the two future Hall of Famers who would subsequently kick the ball out to the open man. Though Pippen was a capable post entry passer, that style of basketball clashed with his game. 

Known for his time as a master ball-handler, cutter, passer and post up player in Chicago’s triangle offense, Pippen was relegated to a spot-up shooting role and a background role in Houston’s offense. A career 32.8% shooter from beyond the arc, Pippen wasn’t the ideal perimeter threat to play off of Barkley and Olajuwon. The Rockets also played a much slower pace than Pippen preferred.

The 1999 postseason saw the Rockets duel with the Los Angeles Lakers in the opening round. In the latter stages of the first game, Lakers guard Kobe Bryant drew a foul on Rockets guard Sam Mack with 5.3 seconds left and nailed two free-throws to give the Lakers a one-point lead. Rockets guard Cuttino Mobley had his layup attempt blocked by Lakers center Shaquille O’Neal as time expired and the Lakers took Game One 101-100.

In the second game, the Lakers jumped out to an early lead and led by as much as 23 points in a 110-98 victory and a 2-0 series lead. Pippen (three points on 0-7 shooting) and Olajuwon (eight points on 3-10 shooting) struggled mightily in the loss. 

Facing elimination, Houston received great performances from Pippen (37 points, 13 rebounds and four assists) and Barkley (30 points, 23 boards and five dimes) as they won easily 102-88 in Game Three. Los Angeles finished off the series with a 98-88 win that saw them lead by as much as 17 points. O’Neal dominated with 37 points and 11 rebounds in the elimination game.

Besides his explosion in Game Three, Pippen was quiet in the series, averaging 18.3 PPG on 32.9% from the field. He shot 27.3% on 22 three-point attempts. Pippen also managed 11.8 RPG, 5.5 APG, 1.8 SPG and 0.8 BPG in the series.

After the season, there were murmurs of Pippen’s disinterest in continuing his career with the Rockets. Rumors of a reunion of Pippen with former Bulls coach and new Lakers coach Phil Jackson swirled throughout the league.

Pippen’s relationship with Barkley had deteriorated at this point. Barkley began to criticize Pippen in the media for wanting to leave the Rockets despite his willingness to sacrifice and take a massive pay cut so the Rockets could add Pippen. Barkley felt blindsided by Pippen’s trade demands, something that Pippen disputed (via Sports Illustrated):

“If anything, Pippen says, Barkley broke a trust when he declared that Pippen hadn't told him personally that he wanted to be traded. ‘He turned around and lied and said I didn’t tell him, when I had spent a week in Hawaii with him,’ Pippen says. ‘Other NBA guys, like Jason Kidd, were there. We all went out to play golf one day, and I spoke to Charles about it. Then he gets back to Houston and starts saying that he’d spent a week with me and I hadn’t said anything. I had.’ (Kidd confirms Pippen's account.)”

Pippen didn’t take too kindly to Barkley’s words, letting loose in an interview with ESPN.

“I wouldn’t give Charles Barkley an apology at gunpoint,” Pippen said with the cameras rolling. “He can never expect an apology from me. If anything, he owes me an apology for coming to play with his sorry fat butt.”

But he wasn’t done there.

“I probably should have listened to Michael [Jordan] a year ago when he said that Charles will never win a championship because he doesn’t show any dedication,” Pippen said. 

“He’s a very selfish guy. He doesn’t show the desire to want to win. That’s my reason for wanting to get away from playing with him, because he just doesn’t show the dedication.”

Pippen’s comments put the Rockets in an uncomfortable position. Knowing their two stars would be unable to coexist, the Rockets made the decision to trade Pippen. Though the Los Angeles Lakers were interested, owner Jerry Buss decided against acquiring Pippen because of the four years remaining on his deal and how it would restrict the Lakers from improving the team in the future.

The Portland Trail Blazers became an option. Looking to add to an already deep roster and create a championship contender, the Blazers acquired Pippen for six players.

Stacey Augmon became a member of the Portland Trail Blazers in the middle of the 1996-97 season, when he was traded by the Detroit Pistons for three players in January of 1997. A lithe wing defender, Augmon played a reserve wing role behind Isaiah Rider for the Blazers. Portland finished fifth in the West with a 49-33 record during the ‘96-‘97 season. Augmon tallied 4.7 PPG, 2.2 RPG, 1.0 APG and 0.8 SPG in 40 contests and 16.3 MPG.

The Blazers battled the 56-26 Los Angeles Lakers in the opening round. The first game was close early on, but the Lakers extended their lead in the fourth quarter with a decisive 15-2 run to put away Portland 95-77. Game Two saw the Lakers lead by as much as 20 as they held on to win 107-93. 

In the third contest, Blazers guard Kenny Anderson had 30 points, five rebounds and five assists as Portland won 98-90. Los Angeles made a decisive 8-0 run late in Game Four and former Blazer Jerome Kersey had some key hustle plays to help the Lakers eke out a 95-91 win and a 3-1 series win. Augmon had a limited role in the first round, averaging 1.8 PPG on 33% from the field in 8.9 MPG.

In the 1997 offseason, the Trail Blazers acquired rookie shotblocking center Kelvin Cato through a draft night deal with the Dallas Mavericks. The Blazers also signed free agent Brian Grant to replace departed veteran Clifford Robinson and add to an already deep roster. The team also let go of coach P.J. Carlesimo and hired Mike Dunleavy as his replacement.

The Blazers were 28-20 during the 1997-98 season when they made a splashy move, acquiring Damon Stoudamire, Carlos Rogers and Walt Williams from the Toronto Raptors for Kenny Anderson, Gary Trent, Alvin Williams, two first round picks and a second round pick. A hometown product from the area, Stoudamire was a high profile addition. 

The Blazers went 18-16 after the deal, finishing with a 46-36 record. Cato was a backup to starter Arvydas Sabonis in his first season. He was an elite rim protector in limited minutes. Cato played in 74 games and posted 3.8 PPG, 3.4 RPG and 1.3 BPG in 13.6 MPG. Augmon had a larger role in his second season with Portland. He played in 71 contests (23 starts), racking up 5.7 PPG, 3.3 RPG, 1.2 APG, 0.8 SPG and 0.5 BPG in 20.4 MPG.

Williams appeared in 31 games for Portland after the midseason, putting up 8.4 PPG, 2.6 RPG, 1.7 APG and 0.6 SPG in 19.2 MPG. Rogers only played in three games, posting 1.3 PPG, 0.7 RPG and 0.7 APG in 8.3 MPG. 

Sixth in the West, Portland went on to the first round of the postseason where they faced the Los Angeles Lakers for the second consecutive season. In the series opener, Lakers guard Kobe Bryant scored 11 of his 15 total points in the final eight and a half minutes, and Shaquille O’Neal had 30 points as the Lakers won by two points.

The second game saw Lakers small forward Rick Fox drop in 24 points as the Lakers won 108-99. In the third game, Rasheed Wallace had nine points in the fourth quarter and the Blazers had multiple contributions in a 99-94 win. The Lakers closed out the series in Game Four 110-99 thanks to 31 points, 15 rebounds, five assists and four blocks from O’Neal.

Cato got a bump in playing time thanks to the need for big bodies to cover O’Neal in the post. In four games, Cato averaged 6.5 PPG, 3.0 RPG and 1.3 BPG in 14.5 MPG. Williams had a solid series, recording 13.3 PPG on 50% from three, 3.5 RPG and 2.3 APG in 25.4 MPG. Augmon saw limited playing time in the first round matchup, posting 1.3 PPG and 0.8 RPG in 6.8 MPG. Rogers did not play in the series.

After the 1998 lockout ended in 1999, Portland signed veterans Greg Anthony and Jim Jackson in free agency. Portland won 15 of their first 18 games. Tied for first in the West after 37 games, a 6-7 finish caused Portland to fall to second seed in the West and third best record in the conference with a 35-15 record. 

Cato played in 43 games in his second pro season and managed 3.5 PPG, 3.5 RPG, 0.5 SPG and 1.3 BPG in 12.7 MPG. Williams appeared in 48 games, and put up 9.3 PPG, 3.0 RPG, 1.7 APG, 0.8 SPG and 0.6 BPG in 21.8 MPG. Augmon continued to steadily decline as an offensive contributor, but still made a significant defensive impact. The wing played in 48 contests (21 starts) and registered 4.3 PPG, 2.6 RPG, 1.2 APG and 1.2 SPG in 18.2 MPG.

Rogers played in just two games, recording five points and one rebound in eight minutes. Brian Shaw joined Portland late in the season, signing a 10-day contract and later signing for the rest of the season. He appeared in one game for the Blazers, going scoreless in five minutes.

Portland matched up with the Phoenix Suns in the first round of the postseason. In the series opener, Portland guard Isaiah Rider scored 25 points as the Blazers won 95-85. 

In the second contest, Brian Grant, Rasheed Wallace and Damon Stoudamire combined for 65 points as Portland won by 11 points to take a 2-0 series lead. In the third game, the Blazers outscored the Suns 34-21 in the fourth quarter to win 103-93 and complete a three-game series sweep. 

Williams managed 4.3 PPG, 1.0 RPG and 1.0 APG in 12.0 MPG during the series. Augmon had 3.7 PPG and 2.0 RPG in 10.5 MPG during the series. Cato played just two games and nine total minutes in the three-game sweep. Rogers and Shaw did not play during the series.

Portland faced the Utah Jazz during the second round of the postseason. The Blazers took a 15-point lead in the first half of the series opener. Utah worked their way back into the game, but Portland still found themselves leading by four points going into the fourth quarter. The Trail Blazers collapsed in the final frame as Utah used a 19-5 scoring edge in the fourth quarter to win 93-83.

The second game in Utah was very close. Portland took a two-point lead late after a Greg Anthony free throw. With 9.2 seconds left, Jazz guard John Stockton missed a potential game-tying layup. Portland ended up taking the game 84-81 and evened the series 1-1.

With the series even, the Blazers took care of business at home. Portland went on a 25-2 run in the first half of Game Three and used that run to propel themselves to a 10-point victory. In the fourth contest, the Blazers won 81-75. Facing elimination, the Jazz got 45 points from Karl Malone and Bryon Russell in an 88-71 win.

Game Six saw Utah close within two points of Portland on a Russell layup and a free throw from Jeff Hornacek with 1:21 left in the game. Portland outscored Utah 12-2 in the final minute-plus (thanks to a bevy of free-throws) to win 92-80 and advance to the Western Conference Finals. 

Williams struggled from the field (32.1% from the field) in the second round, but managed 5.3 PPG. Augmon put up 2.0 PPG and 2.8 RPG during the series. Cato made appearances in three of the six games, scoring one point in 18 minutes.

The Blazers made the Western Conference Finals for the first time since 1992 and faced the San Antonio Spurs. In the series opener, San Antonio’s duo of Tim Duncan and David Robinson scored 21 points each. Rasheed Wallace missed a potential game-tying jumper with 16 seconds left as the Spurs won 80-76.

In Game Two, Portland built an 18-point lead in the third quarter. San Antonio got back into the game, cutting the lead to one after free-throws from Spurs guard Mario Elie. On Portland’s next possession, Damon Stoudamire missed a midrange attempt, but Walt Williams rebounded the missed attempt. The Spurs fouled Stoudamire intentionally with 12 seconds left. He subsequently split the free-throws to give the Blazers a two-point lead.

On the next possession, Elie inbounded the ball to Spurs forward Elliott in the right corner and Elliott made a three over the outstretched arms of Wallace with nine seconds remaining. The shot would go on to be known as the Memorial Day Miracle. On the final possession, Jim Jackson was blocked on his shot attempt. Williams rebounded the ball, but his fadeaway banker was off as San Antonio won 86-85 and took a 2-0 series lead.

The Spurs stymied the Blazers in the second half of Game Three. They held the Blazers to just eight points in 12 minutes during the third quarter and ran away with an 85-63 victory. The Spurs pulled away late in four game as they completed the sweep with a 94-80 win on Portland’s home floor. 

Williams logged 4.5 PPG, 2.0 RPG, 1.5 APG and 0.8 SPG in the four-game sweep. Augmon averaged 3.0 PPG, 2.5 RPG and 0.8 SPG in 13.0 MPG. Cato appeared in three of the four games during the series, scoring just one point in 16 total minutes. Shaw and Rogers did not play at all during Portland’s 1999 playoff run.

Looking to retool after the Conference Finals sweep, the Blazers wanted to make a big splash. They first got down to business, dealing Isaiah Rider and Jim Jackson to the Atlanta Hawks for All-Star guard Steve Smith and Ed Gray. Soon after, they would make another big move, acquiring Scottie Pippen. Involved in the deal was Cato, Augmon, Williams, Shaw, Rogers and the recently acquired Gray.

After the trade, Ed Gray and Brian Shaw were both waived by the Rockets a few days after the trade. Shaw was a free agent, but signed a deal with Portland to be included in the Pippen deal, pocketing the minimum salary when he was waived by Houston. He ended up signing a deal with the Los Angeles Lakers soon after. 

Augmon joined the Rockets for 10 days before he was waived in training camp. He ended up returning to Portland, signing for the minimum. Cato ended up impressing the Rockets in training camp. He averaged 5.3 BPG in preseason and the Rockets committed to the young center, signing him to a six-year, $42 million contract extension. 

Walt Williams became the starter at small forward for Houston and Cato assumed a role as a backup center to veteran Hakeem Olajuwon. Barkley appeared in 20 games for the Rockets before suffering a ruptured right quadriceps tendon that led to his retirement. Olajuwon was limited to 44 games due to an inguinal hernia that required surgery.

Houston began the 1999-00 season 2-10. With their veteran stars both out for long periods of time, rookie Steve Francis and shooting guard Cuttino Mobley took control of the offense. Francis was named co-Rookie of the Year with Chicago Bulls forward Elton Brand. Houston went 34-48 during the ‘99-‘00 campaign, missing the postseason for the first time in eight years. 

Williams played in 76 games (66 starts), and amassed 10.9 PPG, 4.2 RPG, 2.1 APG, 0.6 SPG and 0.6 BPG in 24.5 MPG. Cato played in 65 games, starting 32 of them. In 24.3 MPG, the big man amassed 8.7 PPG, 6.0 RPG, 0.5 APG and 1.9 BPG in 24.3 MPG. Carlos Rogers appeared in 53 games (15 starts) and produced 8.0 PPG, 5.2 RPG, 0.8 APG and 0.6 BPG in 20.8 MPG. 

For the 2000-01 season, Houston didn’t do much to alter their roster. Barkley retired and the team replaced him with free agent acquisition Maurice Taylor. Houston was a surprise team during the 2000-01 season. They finished the season with a 45-37 record. Still, Houston failed to qualify for the playoffs, finishing two games behind the final playoff spot.

Williams was a starter at small forward during the 2000-01 season, but lost the spot to Cuttino Mobley early on in the season. “The Wizard” appeared in 72 games (31 starts) and finished with 8.3 PPG, 3.4 RPG, and 1.3 APG in 22.0 MPG.

Cato was snake-bitten with injuries (sprained both ankles, and torn left rotator cuff) as he only played in 32 games. Cato managed 4.7 PPG, 4.0 RPG and 0.9 BPG in 17.8 MPG. Rogers had a lesser role in his second season with Houston. The lanky big, compiled 4.6 PPG, 3.6 RPG and 0.5 BPG in 39 contests and 13.9 MPG.

In the 2001 offseason, the Rockets dealt center Hakeem Olajuwon to the Toronto Raptors. With the move of Olajuwon, Cato would become the team’s starting center for the 2001-02 season. Rogers’ team option for the ‘01-‘02 season was declined by the Rockets. He ended up signing a deal with the Indiana Pacers. Rogers ended his Rockets tenure with averages of 6.5 PPG, 4.5 RPG, 0.6 APG and 0.6 BPG in 92 games. He shot 56% from the field and 58% from the free-throw line in that time.

In the 2001 NBA Draft, the Rockets drafted Stanford center Jason Collins. Houston subsequently traded Collins and their two other first rounders in Richard Jefferson (13th drafted) and Brandon Armstrong (23rd ) to the New Jersey Nets for the rights to the seventh overall pick, Eddie Griffin.

Houston began the ‘01-‘02 campaign 7-5, but fell apart due to injuries. The team finished 28-54 that season. Francis missed 25 games and key bench acquisition Glen Rice was limited to 20 contests due to injury. 

Williams was hurt as well, missing 34 games, primarily due to a right ankle injury. Williams managed 9.4 PPG, 3.4 RPG and 1.4 APG in 23.3 MPG. Cato appeared in 75 games (73 starts) and tallied 6.6 PPG, 7.0 RPG, 0.5 SPG and 1.3 BPG in 25.6 MPG.

Due to Houston’s bad performance, they had more ping pong balls and won the NBA Draft lottery. There, they took center Yao Ming with the first overall pick in the 2002 NBA Draft. Standing at 7′4″ tall, Yao was from China and featured a unique skill set. Despite his massive size, he had a soft touch and was capable of making plays on both ends of the court.

Williams became a free agent and left the Rockets, signing with the Dallas Mavericks for the minimum of $1.3 million. With Yao on the team, Cato was pushed back to a bench role. Houston got off to a 23-15 start with Yao and Francis leading the team. 

The team had its ups and downs, but was in the thick of the Western Conference playoff race. Houston ended up just one game short of the playoffs after they finished with a 43-39 record. As the backup center, Cato played in 73 contests (five starts) and registered 4.5 PPG, 5.9 RPG, 0.5 SPG and 1.2 BPG in 17.1 MPG.

After the ‘02-‘03 season, Rockets head coach Rudy Tomjanovich stepped down and the Rockets hired former Knicks coach Jeff Van Gundy. A full-time center, Cato started at the power forward for the entire 2003-04 season.

The presence of the 6-foot-11 Cato and the 7-foot-3 Yao Houston gave Houston a fierce rim-protecting duo despite a lack of quality perimeter defenders. Under Van Gundy, the Rockets managed to finish the season fifth in defensive efficiency. After 65 games, the Rockets were 39-26. Houston went 6-11 in their final 17 games to finish 45-37. The Rockets earned the seventh seed in the Western Conference.

In the 2004 postseason, Houston matched up with the Los Angeles Lakers in the first round. A series that became hyped for the showdown between centers Shaquille O’Neal and Yao. Houston led late in the first game, but they lost the lead after an O’Neal putback dunk with 17.4 seconds left put the Lakers up 72-71. O’Neal was fouled on the play by Yao, but missed the free-throw. On the last possession, Francis found Jim Jackson open in the corner, but Jackson missed before the buzzer sounded.

In the second game, Kobe Bryant had 36 points for the Lakers as they dominated the second half and won 98-84. Facing a 2-0 deficit, Francis carried the Rockets with 27 points, nine rebounds and seven dimes as Houston took their first game of the series 102-91. 

The fourth game was close in its latter stages. Francis tied the game at 81 with a midrange jumper with 39.1 seconds left. Bryant missed a shot at the buzzer to win the game. In the overtime of Game Three, Bryant and Karl Malone scored 10 of Los Angeles’ 11 points as the Lakers won 92-88. 

The fifth and final game saw Los Angeles lead by as much as 26 points as they easily won 97-78 and eliminated Houston. During the first round series, Cato started all five games. He compiled 5.8 PPG on 59.1% from the field, 6.8 RPG, 1.0 SPG and 0.8 BPG in 29.2 MPG.

After the season, Cato was involved in a seven-player deal involving the Orlando Magic that centered around Tracy McGrady heading to Houston and Francis and Mobley departing for the Magic. Cato finished his time in Houston with stats of 6.2 PPG, 6.2 RPG, 0.5 APG, 0.6 SPG and 1.4 BPG in 317 contests. The former Iowa State product shot 53% from the field and 62% from the free-throw line.

After the addition of Scottie Pippen, Portland was viewed as one of the elite teams of the NBA. A legitimate title contender, the Blazers had a surplus of talent with former All-Stars in Pippen, new acquisition Steve Smith and veteran Detlef Schrempf added to the roster. With young impact players like Brian Grant, Rasheed Wallace and Damon Stoudamire, the team was stacked. 

Portland won 10 of its first 11 games. There were some growing pains trying to acclimate the luxurious compilation of talent, but soon the team would begin to gel. At one point, Portland was a dominant 45-11. Tied with the Lakers for the top record in the NBA at that point, Portland faltered down the stretch, going 14-12 over its final 26 games to finish with the second best record in the West at 59-23.

Pippen had reduced numbers due to Portland’s deep roster, but he was still his usual multi-faceted self. A great post-up option, slasher and defender, the former champion posted 12.5 PPG, 6.3 RPG, 5.0 APG, 1.4 SPG and 0.5 BPG in 82 games and 33.5 MPG. He made his 10th overall NBA All-Defensive Team (Second).

In the first round of the playoffs, Portland faced the sixth-seeded Minnesota Timberwolves. Game One was close throughout. Minnesota led by six points with 10:35 left in the fourth quarter. The Blazers proceeded to go on a 16-5 run to take control over the next nine minutes and maintain their lead in a 91-88 win. Pippen had 28 points and nine rebounds in the victory. 

The Blazers took a 2-0 lead after Pippen contributed 21 points and seven rebounds in another close contest. Minnesota’s bright young star Kevin Garnett kept Minnesota in the series. He had a triple double (23 points, 13 rebounds and 10 assists) in a 94-87 victory, making the series 2-1 in Portland’s favor. 

The Blazers bounced back in Game Four. Down by 13 in the first half, Portland battled back to tie the game and even take a lead by the third quarter. In the fourth, the Wolves took a 75-74 lead after Garnett made two free-throws with 4:08 left in the fourth quarter. Portland went on an 11-2 run to win the game 85-77 and take the series 3-1. Pippen stepped up in the series, averaging 18.8 PPG on 41.9% from the field, as well as 7.0 RPG, 4.3 APG and 1.3 SPG in 39.5 MPG.

Portland took on the Utah Jazz in the Semifinals. In the series opener, Pippen had 20 points and three steals as Portland pulled away late to win 94-75. The second game was a similar story as the Blazers led by 21 points at the half. Portland’s lead reached as high as 33 as they kept their distance in a 103-85 win. 

As the series scene shifted to Utah, Portland kept their foot on the veteran Jazz’ neck. Arvydas Sabonis had 22 points and eight rebounds as the Blazers took a 3-0 series lead with a 103-84 victory. In Game Four, Jazz star Karl Malone carried his team. He had 27 points, eight rebounds and seven assists as Utah managed to survive elimination with a three-point win. Portland had a chance to tie late, but Greg Anthony missed a three-point shot at the buzzer.

In Game Five, the Jazz led for much of the action by single digits. Late in the game Pippen knocked down a triple with 7.3 seconds left that gave Portland an 80-79 lead.

Video via Portland Trail Blazers

Jazz wing Bryon Russell was fouled by Detlef Schrempf on the ensuing possession, but missed both free-throws. Pippen collected the rebound, was fouled, and made one of two free-throws. Trailing by two, Russell missed a three at the buzzer as Portland held on for an 81-79 win and a 4-1 series triumph. In the second round series, Pippen was relatively quiet with 11.6 PPG, 4.6 RPG, 5.2 APG and 1.8 SPG in 32.6 MPG.

Portland faced the Los Angeles Lakers in the Western Conference Finals. NBA regular season MVP Shaquille O’Neal was dominant in the series opener, recording 41 points, 11 rebounds and five blocks as the Lakers took the first game 109-94. Portland came back in Game Two, and outscored the Lakers 58-32 in the second half in a 106-77 win on the road. 

Game Three was much closer than the previous two contests. A baseline jumper from Ron Harper and a Kobe Bryant block of an Arvydas Sabonis runner sealed a 93-91 win for Los Angeles. Los Angeles stunned Portland in Game Four, taking a 3-1 series lead with a 103-91 win in the fourth game.

Pippen galvanized his teammates pregame by showing off his six championship rings with the Chicago Bulls. The former champ had a throwback game, scoring 22 points and also pitching in with six rebounds, six steals and four blocks. Portland built a 13-point lead through three quarters and ended up winning by eight points. Steve Smith had 26 points in Game Six and Bonzi Wells chipped in 20 off the bench as Portland forced a Game Seven with a 107-97 victory.

In the final game, the Trail Blazers threw the first punches in this heavyweight battle. They had the Lakers on the ropes as they led 71-55 with 20.6 seconds left in the third quarter. Portland led 75-60 with 10:28 left, but the Lakers ran off 15 unanswered to tie the game by the four-minute mark. In the final four, the Lakers shellshocked the Blazers, outscoring them 14-9 to make a surprising comeback. A Bryant to O’Neal alley-oop signaled a crushing end to Portland’s 1999-00 season.

Pippen did a little bit of everything for Portland in the seven-game Conference Finals loss. In 41.9 MPG, Pippen averaged 15.1 PPG on 42.5% from the field, 9.0 RPG, 3.7 APG, 2.6 SPG and 0.9 BPG.

Looking to compete with the Lakers, the Trail Blazers retooled for the 2000-01 season. They traded young big man Jermaine O’Neal to the Indiana Pacers for veteran Dale Davis. Blazers forward Brian Grant became a free agent and was signed-and-traded to the Miami Heat in a three-team deal with the Cleveland Cavaliers that brought former All-Star Shawn Kemp to Portland. 

Portland had a talented roster after the moves. After a shaky start, the Blazers looked good. They were 27-10 after 37 games. Portland had the best record in the West in early March at 42-18. However, they went 8-14 the rest of the way to finish 50-32. The late-season slide dropped them all the way down to the seventh seed. Drama seemed to follow the Blazers the entire season.

Kemp was out of shape from the start of training camp and struggled to live up to his pricy salary. He eventually had to leave the Blazers late in the season to check into the NBA’s substance-abuse treatment program for cocaine. Guard Bonzi Wells tore his ACL late in the season.

Wallace was still productive, but he became a volatile personality. He set the NBA record 41 technical fouls during the season. This eventually caused coach Mike Dunleavy to later suspend Wallace. The All-Star forward was suspended for two games and fined $10,000 for throwing a towel that hit referee Gary Benson in the face. 

Wallace also threw a towel in the face of teammate Arvydas Sabonis after an incident where Sabonis accidentally hit Wallace in the face during the penultimate game of the season against the Lakers. Wallace was suspended for the last game of the season. Midseason acquisitions of veterans Rod Strickland and Detlef Schrempf also added more problems than solutions for Portland. 

In his 14th season, Pippen dealt with injuries and declining play. An arthroscopic surgery to remove a bone fragment in his right elbow, caused Pippen to miss 18 games. In 64 contests, Pippen compiled 11.3 PPG, 5.2 RPG, 4.6 APG, 1.5 SPG and 0.5 BPG in 33.3 MPG.

Portland went on to the postseason where they faced their rivals, the Lakers in the opening round. The first game featured a key Lakers 19-0 run bridging the third and fourth quarters that allowed the Lakers to comfortably win 106-93. The Blazers got off to a solid start in Game Two, but they fell apart, falling behind by double digits in the second half. 

The team lost their cool in embarrassing fashion later on. Dale Davis and Rasheed Wallace were ejected and the team picked up five technical fouls overall in the fourth quarter of a 106-88 loss.

Facing elimination, Portland’s guards Damon Stoudamire and Steve Smith (25 points each) fought, but the Lakers’ duo of Kobe Bryant and Shaquille O’Neal (47 points combined) led the Lakers to a sweep of Portland with a 99-86 win. Pippen struggled in the elimination game, shooting just 3-for-13 in the loss.

Overall, Pippen was one of many Blazers that had a rough three-game performance in the first round. He produced 13.7 PPG on 42.1% on FGs, 5.7 RPG, 2.3 APG, 2.7 SPG and 0.7 BPG in 39.0 MPG.

After the massively disappointing ‘00-‘01 season, the Blazers fired head coach Mike Dunleavy. They hired Philadelphia 76ers assistant Maurice Cheeks to give the veteran team a new voice. 

On the personnel front, Portland signed forward Ruben Patterson away from the Seattle Supersonics. The Blazers acquired guard Derek Anderson in a sign-and trade that saw the team deal Steve Smith to the San Antonio Spurs. They also traded point guard Greg Anthony to the Chicago Bulls and lost Stacey Augmon to the Charlotte Hornets in free agency. Center Arvydas Sabonis went back to Europe for the 2001-02 season. 

The departure of Smith made Wells the permanent starter in Portland. Wells angered the local fanbase early in the season after a Sports Illustrated feature, featured a divisive quote about the relationship between Blazers fans and players.

“We’re not really going to worry about what the hell [the fans] think about us. They really don’t matter to us. They can boo us every day, but they’re still going to ask for our autographs if they see us on the street. That’s why they’re fans and we’re NBA players.”

The quote highlighted a rift between Blazers fans — and the media — and the players. The player arrests off the court, suspensions, and negative stories started to pile up and the Blazers carried the nickname “The Jailblazers.” Once a team with so much promise, the franchise became clouded with stories and negativity that seemed to disrupt any chance of success with the team.

Portland got off to a 13-18 start after the first 31 games of the 2001-02 season. They were just 26-24 after the first 50 games. Soon after, Portland won 12 consecutive games and 17 of their next 19 games to reach 43-26. They finished the season 6-7 to finish up 49-33. Pippen missed time due to a deep bruise on his right knee that would later require surgery. He ended the season with stats of 10.6 PPG, 5.2 RPG, 5.9 APG, 1.6 SPG and 0.6 BPG in 62 appearances and 32.2 MPG.

The Blazers entered the 2002 postseason as the sixth seed in the West. They faced the Los Angeles Lakers in the first round for the second consecutive year and in a playoff series for the third consecutive time. In Game One, Kobe Bryant had 34 points and Shaquille O’Neal had 25 points in a 95-87 Lakers win. In Game Two, Pippen had 20 points and nine rebounds, but the Lakers never trailed on their way to a 2-0 series lead and a 103-96 victory.

Game Three was close but ended up in heartbreaking fashion for Portland. After Portland took a four-point lead with 17.1 seconds left, Bryant converted in a three-point shot to make the game a one point deficit. After Pippen made one free-throw with 10.8 seconds left, Robert Horry knocked down a three-pointer in the corner that gave the Lakers a 92-91 lead with 2.1 seconds left. 

Pippen turned the ball over on the final possession, giving the Lakers the win and the series. Pippen put up 16.3 PPG while shooting 46.2% on FGs during the series. The forward also registered 9.3 RPG, 5.7 APG, 1.3 SPG and 0.7 BPG in 32.9 MPG.

The Blazers kept much of their core intact, making minor moves such as the additions of guards Jeff McInnis and Antonio Daniels. Portland had a lukewarm beginning to the 2002-03 season. Coach Cheeks benched Damon Stoudamire and handed the starting point guard position over to Pippen — who was starting at small forward. 

After a 3-6 start to the season, the Blazers went 33-14 with Pippen at point guard before he sat out due to arthroscopic surgery on his left knee. Pippen returned for the final two games of the season as Portland finished 50-32 and earned the sixth seed in the West. Pippen finished up the ‘02-‘03 season with a stat line of 64 games played, 10.8 PPG, 4.3 RPG, 4.5 APG and 1.6 SPG in 29.9 MPG.

The Blazers were finally blessed by the basketball gods by not facing the Los Angeles Lakers in the first round. Still, they matched up with one of the better teams in the NBA in the Dallas Mavericks. Portland took an early double digit lead in Dallas, but Mavericks star Dirk Nowitzki scored a franchise-record 46 points to carry Dallas to a strong 96-86 win in the first game.

Wells had 45 points to lead the Blazers in Game Two, but it was not enough. Mavericks guard Steve Nash broke a tie with a three with 29.7 seconds left and made two free-throws later on to give Dallas the 103-99 decision. Nowitzki had 42 points and 10 rebounds as Dallas led for nearly the entire time in a Game Three 115-103 win.

Facing a 3-0 series deficit and a 10-game playoff losing streak spanning three years, the Trail Blazers had enough. Zach Randolph had 25 points and 15 rebounds, and Portland outscored Dallas 33-10 in the third quarter as they finally won a game with a 98-79 win in the fourth contest. In Game Five, the Mavericks led for the first 46 minutes and 55 seconds, but the Blazers made a late run, outscoring Dallas 12-3 in the final 3:46 to win 103-99 and keep hope alive. The sixth game was a laugher as the Blazers led by as much as 32 points in a 125-103 win. Six Blazers scored at least 13 points.

With all the momentum and the chance to make history as the first team to come back from a 3-0 series deficit, Portland challenged Dallas on the road in Game Seven. The game was close for most of the action, but Dallas took control late and won 107-95 with Dirk Nowitzki (31 points and 11 boards) and Nick Van Exel (26 points) leading the way. Pippen was severely limited by his left knee, missing three games in the series and playing minor minutes. He put up a paltry 5.8 PPG, 2.8 RPG and 3.3 APG in four games.

After the season ended, Blazers president and general manager Bob Whitsitt stepped down, marking the end of Portland’s quest to cobble together a roster of high-priced veterans. The team hired Steve Patterson as president and John Nash as general manager to run the team and build for the future.

At the age of 37, Pippen departed the Blazers in free agency and signed a two-year with his former team the Chicago Bulls. The former six-time champ ended his run in Portland with a stat line of 11.4 PPG, 5.3 RPG, 5.0 APG, 1.5 SPG and 0.5 BPG. In 272 games with the Blazers roster, Pippen shot 44% from the field, 32% from the three-point line and 76% from the free-throw line. 

Though he wasn’t able to elevate his team to a championship, Pippen’s play and leadership got the team within striking distance of a Finals appearance in 2000. Injuries, failed team chemistry and inability to close out close games doomed Portland the final three years of Pippen’s tenure.

Scottie Pippen on heading to Portland (via ESPN):

“This is a great fit for me. If I had my choice, I would probably choose this team because I feel like they’re more on the verge of winning a championship.”

On why Houston didn’t work out:

“Things just didn’t work out in Houston for me. To some degree I wasn’t the right fit for that team. I think Portland is a better fit.”

How there will be a battle for minutes with Portland’s deep roster:

“I see Mike having a very tough job trying to get guys minutes out on the court, but we have to be one happy family, and realize that the most important thing is about winning.”

On Houston’s lack of desire to compete for a championship (via The Galveston Daily News):

“I wouldn’t exactly say I wanted to be traded, no. I wanted to see that we were a team that was trying to win a championship. That was my main reason for going there, and I felt like that at some point we sort of gave up on ourselves. We didn’t want to win.”

On the talent of the Blazers (via Austin American-Statesman):

“I think talent-wise this team is far more talented than any that’s (ever) been assembled in this league because of the versatility that they bring. I’ve never been on a team, other than the Dream Team or an All-Star team, where so many players draw attention. It’s pretty scary when you think of the lineups we can play with.”

How he feels that his comments about Barkley were responses to what Barkley was saying and how he feels that Barkley utilized his relationship with the media:

“I really just made a response back to what Charles was saying. The media really plays up to him and some took offense to what I was saying. It doesn’t bother me. I’ve been dealing with that type of scrutiny my whole career. Playing with Michael [Jordan], I realized someone had to take the blows. I go to Houston, where Charles is the guy the media loves to talk to. So they have to cover up for him a little bit.”

How the one season in Houston was difficult:

“Last season was a bit of a struggle for me. Being in a different system and having to cater to two superstars... I wouldn’t exactly say I wanted to be traded. I wanted to see if we were a team that was trying to win a championship. That was my main reason for going there.”

How he feels the Blazers are the favorites to win a championship:

“I feel this team is far more talented than the Lakers. [The Blazers are] far ahead, of where the Lakers are trying to get because they are a team that plays well together, knows how to win. [Houston] was one of the only; teams in the West to play more a half-court game, [and] I didn’t feel I would ever blend with that team; because we weren’t putting in the time to make the blend happen.

“I’m not disappointed at all, about being here. If I had my choice, I’d probably choose this team because I feel like they’re more on the verge of winning a championship instead of the Lakers.”

Kelvin Cato on getting a chance to play with Charles Barkley and Hakeem Olajuwon in Houston (via The Galveston Daily News):

“Playing with Charles and playing with Hakeem is going to be great. My main thing is hoping they like me as much as I idolized them as I grew up.”

Portland Trail Blazers president of basketball operations and general manager Bob Whitsitt on rumors that Pippen was upset with the trade (via Racine Journal Times):

“I talked with Scottie on the phone, and he said, ‘That L.A. stuff was blown out of proportion. I love Portland and I like what’s going on.”

How the team doesn’t need Scottie Pippen to produce superb statistics (via ESPN):

“If Scottie averages 14 [points], seven rebounds, seven assists and two steals ever year for the next four years, perfect. We'll take that in a heartbeat.”

Houston Rockets vice president of basketball operations Carroll Dawson on the trade (via Marianas Variety News and Views):

“The deal is what we got. We deal in reality.”

Houston Rockets head coach Rudy Tomjanovich on Walt Williams (via the Victoria Advocate):

“He’s a pretty versatile offensive player. He has a great 3-point shot and he can also put the ball on the floor and create things.”

On the trade (via ESPN):

“We’re moving forward. I think we’ve taken a negative situation and tried to turn it into a positive.”

How playing for the Rockets was an adjustment for Pippen:

“When you play that style of basketball (with the Bulls), I understood it would take some time to adjust.”

How his last conversation went with Pippen:

“It was very professional. We wished each other luck.”

Trail Blazers head coach Mike Dunleavy on Pippen (via Sports Illustrated):

“He may not be the greatest go-to guy in the world. If I’m going to start a team and pick one guy, there are a lot of other guys I’d pick. But he has the ability to make all your guys go-to guys. He makes everybody better.”

Blazers forward-center Brian Grant on Pippen’s comments that the Blazers have one of the greatest collections of talent in the league (via CBS News):

“We feel great about that. We know he’s not just saying it. We know he really, truly, honestly believes that, so we’re going to go out there and try to do everything we can to prove that he's right.”

Pippen’s agent Jimmy Sexton (via Racine Journal Times):

“After Scottie evaluated the situation in Portland, looked at their roster, what they did last year and the pieces they’ve added, he was excited. They’ll have a legitimate chance to win the NBA championship.”

Pippen’s then-wife Larsa on the criticism Pippen faced in Houston (via Sports Illustrated):

“He gets a lot of criticism because he wanted to be traded, almost like, hate him because he wants to be a winner. That’s the part most people don’t get. The [Houston] team was sorry. None of them wanted to work hard, and then they wanted to win.”

Image Credit: 

Scottie Pippen via Getty Images/The Sporting News

Kelvin Cato via Getty Images/The Sporting News

Carlos Rogers via Getty Images/Icon Sportswire/Matt A. Brown