Every team in the NBA has endured a troubling season where nothing seems to go right. Players underperform and clash with the coaching staff, and general managers make trades that make you scratch your head when broken down years later. During the 2008-2009 season, this is exactly what happened to the Toronto Raptors.

While they have since bounced back from this trainwreck of a season, Raptors fans still look back and wonder what could have been.

During their 07-08 season, the Raptors had posted a respectable 41-41 record, good enough for the sixth seed in the Eastern Conference. They were quickly ousted by the Magic in 5 games, but the future looked bright.

Raptors
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Things began to go downhill during the 08-09 offseason. GM Bryan Colangelo (now infamous for his burner accounts in Philly) swapped the 17th pick to acquire Jermaine O'Neal, who was already in decline from his glory days in Indiana.

O'Neal ended up playing only 41 games for Toronto and averaging only 13.6 points, well below the 21.6 he had averaged while playing for the Pacers. The Raptors plummeted in the standings, leading to a coaching change from Sam Mitchell to Jay Triano and a public outburst from star Chris Bosh after an overtime loss. Colangelo decided to cut ties with O'Neal.

Unfortunately for the Raptors, O'Neal was swapped for yet another past-his-prime star in Shawn Marion. Marion posted solid numbers for the Raptors, averaging 14.3 points and 8.3 boards, but their losing ways continued. A 97-127 drubbing by the Knicks and a 7-game losing streak saw the team hit a new low.

Shawn Marion, Kawhi Leonard

They were eliminated from playoff contention and placed 13th in the conference.  Marion was not offered a new contract, in an effort to remake the roster yet again.

The first move the raptors made in the 09-10 offseason was to replace Marion with Hedo Turkoglu. The signing of the Turkish forward is widely considered to be the worst free agent signings in Raptor's history. Turkoglu has impressed with the Magic, but could not live up to the hype in Toronto. His numbers dropped immediately, averaging 1 less rebound, 1 less assist, and 5 fewer points than the previous season.

Turkoglu was benched but didn't seem to care. He was spotted at a nightclub the same night. Turkoglu publicly berated Raptors management, claiming he was mistreated and demanding a trade.  The nightmare of a signing ended when he was shipped to the Phoenix Suns.

enes kanter, hedo turkoglu

In the span of two seasons, the Raptors had completely imploded.  The poor roster decisions and public feuds more than likely played a part in the departure of Chris Bosh to the Heat, creating “The Heatles” with LeBron James and Dwayne Wade.

No player wanted to be a part of the mess that was the Toronto Raptors. They were forced to start from square one, building from young draft pick DeMar DeRozan.  It would take them 5 years before they reached the playoffs again.

The Raptors 08-09 season shows how three roster moves can cost a franchise five years of competitiveness.   Thankfully for the Raptors organization, they are back to being title contenders with a bonafide star in Kawhi Leonard for at least one season. However, Raptors fans will always contemplate on how this successful run could've come much sooner if not for some poor personnel decisions.