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Bulls, Michael Jordan, Derrick Rose, Jay Williams

Most heartbreaking moments in Chicago Bulls history

There’s no doubt that the Chicago Bulls were the most dominant team in the 1990s. Having won no less than six championships between 1991 and 1998, the Michael Jordan-led Bulls established their unrivaled dynasty in the ’90s, and they will forever go down in history as one of the greatest teams this league has ever seen.

Nonetheless, the Bulls have had their fair share of dark days as well. Even during their reign in the ’90s, they simply could not escape heartbreak. A case in point was Jordan’s decision to turn his back on the franchise when he retired in 1993. We will be talking more about that specific moment later, but for now, we present our Top 3 most heartbreaking moments in Chicago Bulls History.

Jay Williams Motorcycle Crash

When Michael Jordan retired for the second time in 1998, the Bulls were left with a pretty horrible team. In their first season without MJ, Chicago would post a depressing 13-37 record, and this would pretty much be the trend for the next few years.

The Bulls finally appeared to be on their way up again when they secured the second overall pick in the 2002 NBA Draft. They used it on Duke standout Jay Williams, who had a tremendous three-year career with the Blue Devils. As a junior, the 6-foot-2 point guard posted averages of 21.3 points, 3.5 rebounds, and 5.3 assists, making him one of the hottest prospects in the coming draft.

Williams had a rather disappointing season as a rookie, but he still had a lot of promise and potential in him. Sadly, the Plainfield, New Jersey native crashed his motorcycle in the summer of 2003, injuring his pelvis, knee, and leg, while also sustaining severe nerve damage. This would end up being a career-ending injury for the once so promising point guard, who was even considered by more than a few as Jordan’s heir apparent.

Williams would go into a state of depression and would struggle with alcohol and drug addiction. At one point, he would even consider committing suicide. Needless to say, Williams was never able to play in the NBA again after that fateful crash.

Derrick Rose Meniscus Tear

Fast forward some six years later and once again, Chicago got their hands on another amazing point guard in the 2008 draft. Selected first overall in a talent-packed draft class, Derrick Rose would more than live up to the high expectations everybody had for him. He would be named an All-Star in just his second season in the league and would set the record as the youngest ever MVP when he won the award in his third season as a 22-year-old.

Unfortunately, the beginning of the end for Rose came in 2012 — in just his fourth year in the NBA — when the reigning MVP would tear his ACL in the playoffs. He would end up missing the entirety of the succeeding season, but this wasn’t even the worst of it.

In November 2013, just 10 games after his highly-anticipated return from the aforementioned ACL injury — Rose would suffer another career-threatening injury. Rose would end up tearing his meniscus, and what makes this so heartbreaking is the fact that Bulls supporters already knew at this point that their cornerstone superstar would never be the same again.

True enough, Rose would re-injure this same meniscus in February of 2015, and would once again require surgery. He would play one final season with the Bulls the following year, before Chicago finally decided to pull the plug on him, trading him to the New York Knicks in the summer of 2016.

Michael Jordan’s First Retirement

As mentioned earlier, Jordan’s second and final retirement from the Bulls didn’t come until 1998. However, this was right after he had won his second three-peat for Chicago, erasing all doubt that he was indeed one of the greatest ever. At that point, Jordan was leaving the game with a sense of fulfillment.

However, there’s no denying that his shock retirement in 1993 marks one of, if not the darkest days in Bulls history. Here we have a 29-year-old MJ in his prime, coming off three consecutive NBA titles, deciding to walk away for the game for good. It is worth noting that Jordan’s father had passed away just months earlier, and this would end up being one of the factors leading to Jordan’s unprecedented decision.

You also need to remember that no one knew he was going to make is comeback just one year later, so at that particular point in time, there is no doubt that Jordan’s decision left more than a few broken hearts not only in Chicago but in the entire sports world as well.