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The Minnesota Timberwolves made their NBA debut in 1989 and celebrated their 30-year anniversary in the 2018-19 season. However, there hasn't really been much to celebrate about given the gloomy three-plus decades the franchise has experienced.
Having made the playoffs just nine times, including eight through the Kevin Garnett era from 1997 to 2004, the team went through more lows than highs. Certainly, they experienced some gut-wrenching moments along the way that would trigger any Wolves fan. Here are some of the most heartbreaking moments in Minnesota Timberwolves history:
Flip Saunders' death
This is a personal one for most Timberwolves fans. Flip Saunders became one of the most beloved figures in the history of the organization.
Saunders was diagnosed with Hodgkins Lymphoma in August 2015. On October 25, 2015, the long-time Timberwolves head coach succumbed to the disease at the age of 60. The entire team dedicated the 2015-16 season to their long-time coach by wearing a patch with his name, “FLIP,” on their jerseys.
Saunders had just returned for a second stint as head coach of Minnesota in the 2014-15 season. He is by far the winningest coach of the franchise, recording 427 wins and a 52.7 percent winning percentage.
Likewise, he coached the Timberwolves in their most successful season as a franchise in the 2003-04 season. With Saunders at the helm, Minnesota won their two playoff series that season and made the Western Conference Finals.
2004 Western Conference Finals
Prior to the 2003-04 season, the Minnesota Timberwolves had bowed out of the first round of the playoffs for seven consecutive years. In the summer of 2003, they acquired All-Star guards Latrell Sprewell and Sam Cassell. With their acquisitions, the Timberwolves emerged as one of the top teams in the league and finished the regular season with the best record in the Western Conference.
Certainly, those 2003-04 Wolves were championship contenders led by league MVP Kevin Garnett alongside their veteran star backcourt tandem. Minnesota displayed an exciting brand of basketball and established themselves as a top-tier team on both ends of the floor. They finally made it past the first round against the rising Denver Nuggets. In round two, they defeated a championship-caliber team in the Sacramento Kings in a grueling 7-game series.
The Timberwolves set a Western Conference Finals date with the three-time champion Los Angeles Lakers. Unfortunately, Cassell, who made his lone All-Star team that season, sustained a hip injury in the most inopportune time and was limited throughout the series. Minnesota went on to lose the series in six games.
Late coach Flip Saunders, who coached the Timberwolves at the time, believes Cassell injured his hip while doing his “big balls” celebration after draining the series-clinching dagger over Sacramento. Cassell and other Timberwolves players from that team have gone on record saying they would have won the title had the clutch veteran point guard been healthy throughout the series. Perhaps, if Cassell opted to showboat differently, Minnesota could very well already have a Larry O'Brien trophy.
End of the Kevin Garnett era
Minnesota was not able to build from the momentum of their most successful season in franchise history in 2003-04. Things went downhill from that point on. In fact, they didn't make the postseason for 14 years after the 2004 playoffs.
After leading Minnesota to the best record in the West and capturing the league MVP, Kevin Garnett saw three consecutive seasons in the lottery while in the midst of his prime. No doubt, Garnett still put up stellar numbers. However, the Timberwolves finished near the bottom of the league standings from 2004-05 to 2006-07.
The All-NBA big man had grown frustrated and requested a trade from Minnesota. The Timberwolves finally traded their franchise superstar in the summer of 2007 to the Boston Celtics, marking the end of the KG era in Minnesota.
The franchise never really recovered after parting ways with Garnett. They certainly haven't done their due diligence in building a playoff-caliber, more so a championship-caliber, team. A decade of draft brain-farts, which will be highlighted by the next section, is a major reason why.
Missing out on Stephen Curry
Minnesota had a chance to make some noise in the 2009 NBA draft when they had back-to-back selections at No. 5 and No. 6. In a baffling move, they selected two point guards with Spanish guard Ricky Rubio going fifth and Syracuse standout Jonny Flynn going 6th.
As we know, the player that went 7th to the Golden State Warriors is Stephen Curry. At the time, Curry wasn't really a high-profile name coming out of college. Despite leading the nation in scoring in his junior year, the Davidson standout had his fair share of naysayers who doubted he could translate well as a point guard in the NBA.
Meanwhile, Rubio was a highly-anticipated prospect from Spain, so maybe we can give them a pass on that one. However, Timberwolves fans would probably never forgive the organization for picking Flynn over Curry. Most mock drafts actually had Curry being selected before Flynn. However, Minnesota seemed to focus on the negative chatter around Curry and missed the chance to draft a generational superstar.
As we know, Curry eventually turned in a Hall of Fame worthy career with the Warriors. He won back-to-back MVPs in 2015 and 2016 and led Golden State to three championships in five NBA Finals appearances from 2015 to 2019. Flynn, on the other hand, was out of the league in three years.
Certainly, missing out on Stephen Curry is the one that stings the most for Timberwolves fans.
