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TSN Raptors Reporter

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With the Toronto Raptors celebrating their 20th anniversary season in 2014-15, Josh Lewenberg and TSN.ca take a look back at the franchise's first two decades with weekly Top Five lists, counting down the standout and signature players and moments in team history.

1. Sent Vince Carter to the Nets for Eric Williams, Aaron Williams, Alonzo Mourning and two first-round picks - Dec. 17, 2004 (Rob Babcock)

Most of the trades you'll find below are really only "bad" in hindsight. The other four deals on this list share a commonality - they're all home run swings that just, for various reasons, didn't connect. On the cusp of reaching the next level or in danger of taking a step back at the time, they were bold, yet shortsighted moves made in the hopes of expediting the building process.

Then there's the Vince Carter deal, an all-timer, that stands out (and man, does it ever stand out) in its own right. The haul Babcock got in exchange for Carter, a disgruntled superstar, was never highly regarded, to put it mildly. 

"What'd we get?," asked Jalen Rose after hearing about the trade. "Richard Jefferson?" 

Even a decade later, Rose - now a broadcaster - still can't believe Toronto's return for the best and most important player in its history.

"Well, the way he was overcome by emotion and the way he shed a couple of tears," said Rose, back in Toronto earlier this season, shortly after Carter was honoured by the franchise. "That's how I felt when we traded him for Aaron, Eric [Williams] and Alonzo Mourning who never was deciding to make the trip. He's the greatest Raptor in team history."

Babcock insists this was the best offer out there and, given Carter's diminishing worth at the time, that may have actually been the case. It shouldn't have come to that - selling low on a player, a 28-year-old, who held top five (top seven or eight, at worst) value just a few years prior.

The result: Carter would go on to revive his career with the Nets, while Mourning was immediately cut - per his request - and the two Williams' combined to play less than 100 underwhelming games in Toronto. One draft pick turned into disappointing forward Joey Graham, while the other was sent to the Knicks as a sweeter in the Rose salary dump a couple years later. It will go down as one of the most lopsided trades in NBA history.

2. Sent T.J. Ford, Rasho Nesterovic, Maceo Baston and the draft rights to Roy Hibbert to the Pacers for Jermaine O'Neal and the draft rights to Nathan Jawai - July 9, 2008 (Bryan Colangelo)

The Raptors had failed to make it out of the first round for the second straight season, taking a small step back after winning their division the year before. Looking to upgrade at the centre position and pair Chris Bosh with an elite defender in the frontcourt, Colangelo gambled on O'Neal, a former all-star coming off a down and injury-plagued season. Toronto sent Ford and Nesterovic, two starters from that division-winning club, to the Pacers along with the 17th overall pick, who turned out to be the player they were looking for all along. In the years to come, Hibbert blossomed into an all-star and the anchor of Indiana's defence while O'Neal never panned out the way Colangelo had hoped, playing just 41 games for the Raptors before being traded once again.

3. Acquired Rudy Gay and Hamed Haddadi from the Grizzlies for Jose Calderon, Ed Davis and a second-round pick - Jan. 20, 2013 (Colangelo)

On paper, this seemed like a coup for Colangelo. Looking to make a big splash and jump-start a middling team in the final year of his deal, the Raptors' GM added a talented scorer in Gay without giving up a player of his caliber (Calderon's contract was expiring and he was splitting time with Kyle Lowry, Davis is a third or fourth big). Without question, the Raptors upgraded the talent on their roster as a result and the initial returns were positive, albeit unsustainable. The Raptors won six of its first eight games after the trade and would finish that season with a .500 record. But Gay was not a fit with the group already assembled in Toronto, evident in their 6-12 start the next year. The problem: too many cooks in the kitchen. Gay and DeMar DeRozan occupied similar real estate on the floor, while Lowry was underutilized playing alongside two ball dominant scorers. Gay was repackaged less than a year later and the rest is history.

4. Acquired Hedo Turkoglu, Devean George and Antoine Wright in a four-team sign and trade for Shawn Marion, Kris Humphries, Nathan Jawai and a second-round pick - July 9, 2009 (Colangelo)

Praised at the time it was consummated, this is another trade that looks a whole lot different in hindsight. While scoring the league's top free-agent prize, Colangelo engineered a rare four-team deal to avoid hitting the salary cap ceiling. Coming off a career year and a Finals appearance with Orlando, Turkoglu - like O'Neal before him - was thought to be the missing pierce, the perfect compliment to Bosh, who was due to become a free agent the following summer. The good vibes did not last long. Turkoglu arrived out of shape, underwhelming on the floor and appearing lazy and disengaged off of it. The Raptors narrowly missed the playoffs that year and Turkoglu was sent packing shortly thereafter. 

5. Acquired Hakeem Olajuwon from the Rockets for a first and second-round pick - Aug. 2, 2001 (Glen Grunwald)

Sensing a theme here? With the Raptors coming their best season at the time - 47 wins and a semifinals appearance - Grunwald went all in on the group that had taken them there. Antonio Davis, Alvin Williams and Jerome Williams were all awarded new deals and the finishing touch was a future Hall of Fame centre by the name of Hakeem Olajuwon. A free agent after 17 legendary seasons with the Rockets, Olajuwon opted to team up with Carter and company in Toronto before calling it a career. To get him in a sign and trade, Grunwald parted with two draft picks, including one first-rounder. As it turns out, the Raps could have used that pick. Olajuwon was hobbled and ineffective in his only season as a Raptor, which coincided with Carter's injury troubles and the team's untimely collapse. Houston selected journeyman Bostjan Nachbar with the Raptors' 15th overall pick in 2002. Toronto won 24 games the following season.

Honourable mention:

Acquired Chris Childs and a first-round pick (Kareem Rush) from the Knicks for Mark Jackson and Muggsy Bogues - Feb. 22, 2001 (Grunwald)

Acquired Lamond Murray and a second-round pick from the Cavaliers for Michael Stewart and a first-round pick (Jared Dudley) - Sept. 25, 2002 (Grunwald)

Sent Chris Bosh to the Heat in a sign and trade for two first-round picks and a trade exemption - July 9, 2010 (Colangelo)

Sent Tracy McGrady to the Magic in a sign and trade for a first-round pick - Aug. 3, 2000 (Grunwald)