The Blazers also traded for All-Star shooting guard Steve Smith as Isaiah Rider and Jim Jackson headed to Atlanta.
Pippen and Smith would join a talented starting lineup in Portland consisting of future four-time All-Star Rasheed Wallace; Arvydas Sabonis, one of the greatest European players ever; and 1996 NBA Rookie of the Year Damon Stoudamire.
And the bench was made up of Bonzi Wells, Detlef Schrempf, Brian Grant, Greg Anthony, Jermaine O'Neal (before he became a six-time All-Star in Indiana) and Stacey Augmon.
Lakers vs. Blazers was the matchup everybody had been waiting for. The Lakers had the dynamic duo of Shaq and Kobe surrounded by a bunch of role players, while the Blazers featured about 10 players who could start for several teams in the league.
The series would go to the maximum seven games. In Game 7, Portland owned a 15-point fourth quarter lead, which they somehow, somehow blew it. They were outscored by the Lakers 31-13 in the quarter as Brian Shaw knocked down a couple of huge threes.
L.A. would win the series and went on to claim the title after beating Reggie Miller's Indiana Pacers in the NBA Finals.
But what if the Blazers didn't suffer that enormous fourth-quarter meltdown and defeated the Lakers?
There's no doubt that they would have knocked off the Pacers in the Finals. Nothing against the Pacers, with players like Miller, Jalen Rose and Rik Smits, they were certainly a talented ball club at the time, but they wouldn't have been able to handle that Portland squad.
It would have been the Blazers' first title since back in 1977, when Bill Walton and the gang stunned Julius Erving's Philadelphia 76ers in the NBA Finals.
Pippen would have received championship ring No. 7. The Hall of Fame forward has often been criticized for failing to win it all without Michael Jordan at his side. But by picking up a ring in Portland, Pippen would be considered more than just MJ's "sidekick."
If the Blazers didn't experience that monumental collapse against the Lakers and had defeated the Pacers in the Finals, Sabonis would have added an NBA championship ring to his Hall of Fame resume.
Sabonis won several titles during his time over in Europe, but never managed to win one in the NBA, after joining the league in 1995.
Also, if the Blazers had won a title, GM Bob Whitsitt might not have made two bold trades in the 2000 offseason.
"Trader Bob" acquired All-Star big man Shawn Kemp in a three-team trade that sent Grant to Miami. And then Dale Davis, another All-Star big man, was picked up in a deal that sent Jermaine O'Neal to the Pacers.
Both Kemp and Davis were obtained to try to stop Shaq in the low post whenever the Blazers matched up with the Lakers. But if Portland had gotten past the the Lakers, there wouldn't have been a major need to bulk up their frontcourt.
Even with a Blazers championship, the infamous "Jail Blazers " era just might have still taken place in Portland. But hey, at least there would be a 2000 NBA championship banner hanging from the rafters in the Rose Garden, right?
That 1999-2000 Blazer roster was stuffed full of quality NBA players. It's too bad they weren't able to get past those lucky Lakers.