During the 1985-86 season, Hakeem Olajuwon had the opportunity to win his first ring at 23 years old. Leading the Houston Rockets to the Finals, he encountered one of the toughest competitions he had ever faced in the championship bout with the Boston Celtics.

The Eastern Conference powerhouse took the trophy, winning the series in six games. After that battle, Olajuwon appears to have realized that the Celtics squad he faced may have been the perfectly put-together team.

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“I have great respect for that team,” the Rockets legend said of the 1985-86 Celtics. “If you want to put an ideal basketball team together, that would be the team. A basketball team is supposed to be big. They had a big front line. And they’re very smart. They don’t waste opportunities. If you take a bad shot, they’re going to capitalize.”

A nightmare for “The Dream”

The 1986 playoffs were supposed to be a dream ride for Hakeem. After dispatching the Sacramento Kings and Denver Nuggets in the first two rounds, he and his Houston crew easily defeated the Los Angeles Lakers in the Western Conference Finals.

What made it more impressive for Olajuwon was that he had to face Kareem Abdul-Jabbar, who was already 39 by then but still averaged over 20 points per contest nonetheless, Magic Johnson, and the Lakers’ vaunted fast-paced offense. It also didn’t matter for the Rockets that the Purple and Gold had won the NBA title the previous year.

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Houston prevailed over the Showtime Lakers in five games to set up a meeting with Boston.

Olajuwon probably thought that his team had enough to beat the Celtics, even offering a dismissive response before the start of the series when asked about the storied franchise. In response, Larry Bird said he would give the then-youngster a “two-week history lesson.”

That’s exactly what happened as Boston and its terrifying frontcourt rotation of Bird, Kevin McHale, Robert Parish, and Bill Walton made life difficult for Hakeem and his twin-tower duo, Ralph Sampson.

The Celts registered resounding wins in the first two meetings, finishing both games with double-digit margins. Houston nearly fell into a 3-0 hole, but a fourth-quarter meltdown from Boston allowed the home team to escape with a 106-104 victory. The foes then traded wins in the following two contests before Bird and company took care of business in Game 6.

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Olajuwon tried his best to steer the Rockets to the championship, averaging 24.7 points and 11.8 rebounds per contest. However, he shot just 47.9 percent from the field, which was still efficient enough but below his standards. He was also a beast on defense, logging 3.2 blocks and 2.3 steals per game, but the “ideal” Celtics’ offense was just too overwhelming for the up-and-coming squad.

Related: “I watched Shawn go to Cleveland and he got big, and I felt that was my fault” – Gary Payton says he feels responsible for the sad end to Kemp’s career

Becoming a part of a title-winning team

The 1994 NBA MVP may have learned his lesson during that fateful bout with Boston, but it took him a long while before he finally reached the Finals again.

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The years after the Rockets’ 1986 Finals appearance saw the organization stumble big time. They had first-round exits from 1988 to 1991 and couldn’t even make the playoffs in 1992. At some point, Olajuwon nearly left, as he felt his contract was not in keeping with his valuable contributions to the franchise. Everything came to a head when the front office accused him of faking a hamstring injury to avoid playing.

Fortunately for Rockets fans, the 12-time All-Star and the management were able to put their differences aside because, in 1994, the team finally landed its first title in history. It even successfully defended the trophy in the following campaign to avoid becoming the first squad to fail to win back-to-back championships since, coincidentally, 1986.

Related: “There were days where, oh man, he had some flashbacks” – When aging Hakeem Olajuwon made Rockets teammates look clownish in practice