Ranking the Raptors' Biggest Free-Agent Signings on the Hedo Scale

The history of the Toronto Raptors has been littered with free-agent signings that have turned out to be cautionary tales, with the team often scrubbing itself clean of wrongdoing in swift fashion. In the Raptors' 20 seasons of existence, the team hasn't had a long history of recruiting players on the open market, and that itself might explain why some of the names its actually convinced to come north of the border didn't pan out.

With free agency underway, and the Raptors having inked both DeMarre Carroll and Cory Joseph to four-year deals, here's a look back at some of the other times the team has dipped into the market with mixed results, from terrible to catastrophic. Note: some of these were in fact sign-and-trades, but in the spirit of making sure Hakeem Olajuwon and Hedo Turkoglu are properly represented, they have been included.

In order to evaluate each of these free-agent signings, we're going to apply a Turkoglu rating, out of five. It's about as simple as it sounds. Five is disastrous, one is OK maybe it wasn't so bad, the in between ratings are self explanatory.

In the summer of 2000, the Raptors had just come off their first playoff appearance in franchise history—a three-game sweep to the New York Knicks in the first round. The team was set to build around Vince Carter and Tracy McGrady, except T-Mac ended up going to Orlando, leaving the Raptors to build around just one superstar (to be fair, T-Mac didn't blossom into one of the best scorers in the league until he left Toronto).

The team had brought in a new head coach in Lenny Wilkens, and had veterans Antonio Davis and Charles Oakley as key cogs, so it went into the free-agent market and nabbed 35-year-old Mark Jackson from the Indiana Pacers, who were just coming off a Finals loss to the Los Angeles Lakers.

Jackson's tenure lasted 54 games (all starts), in which he averaged 8.5 points and 9.2 assists in 33.4 minutes per game. He did have one moment that's enshrined on YouTube, when he became the all-time leader in assists per game:

He was traded to the Knicks in March, and on his way out, had some not-so-nice things to say about the franchise, including how it wasn't able to keep McGrady. Davis—a teammate of Jackson's from their time together at Indiana—also questioned the Raptors' franchise with regards to player loyalty. From a basketball standpoint, the move opened up space for Alvin Williams to flourish as the starting point guard. The Raptors would meet Jackson and the Knicks in the playoffs, and beat them in five games.

These days, any mention of Olajuwon's tenure with the Raptors is greeted with a shake of the head and some laughter to diffuse the despair of having a memory of it ever happening. But, at the time, and please hold your laughs, it really felt like the final piece to the championship puzzle for the Raptors, who spent all summer locking up a core that had just come within a game of reaching the Eastern Conference finals.

Olajuwon—a 12-time All-Star, a Most Valuable Player in 1994 and two-time Finals MVP and champion—said as much at his introductory press conference: "This team has all that it takes to get to the NBA Finals." When you get an assessment like that from a Hall of Famer, it has to count for something.

Olajuwon was at the tail end of his career, but also wasn't expected to shoulder the load, not on a team with Carter entering his prime. Still, he was a complete disappointment, like ordering a pair of classic sneakers on eBay only to find out they are knockoffs that actually read JORDON on the back.

The Raptors didn't get out of the first round that season, and while Olajuwon wasn't the lone culprit in a disappointing season, he did not contribute much, playing 61 games and averaging 7.1 points and 6.0 rebounds in 22.6 minutes. It would be his last season in the NBA.

Now this was a disaster. The Raptors were going through a bit of turmoil as a franchise heading into the 2004-05 season. Sam Mitchell was hired for his first NBA head coaching gig, Carter would be traded to the New Jersey Nets early in the season, and it left a void that Alston, who had played for the Raptors previously in 2002, tried to fill.

There are numerous stories that have since emerged from Alston's tumultuous season in Toronto. He threatened to quit the team and retire from the NBA after a December 3rd game, was suspended two games for walking out of practice, and butted heads with Mitchell, with reports that the coach challenged his point guard to a fight at one point (Alston, after he left the Raptors, would criticize Mitchell's coaching and question his ability to prepare an NBA team). Jalen Rose once recalled how Alston refused to pass the ball to him and Morris Peterson, and it would take Mitchell's intervention to fix the situation.

To summarize: it was a mess. Alston was traded to the Houston Rockets for Mike James after just one season into his contract.

This was another signing by the Raptors which made perfect sense at the time, but in retrospect simply did not work out. When Kapono agreed to join the Raptors, he was coming off a season in Miami in which he shot 51.4 percent from deep and averaged 10.9 points per game. Kapono also won the 3-point contest at All-Star Weekend (and would defend the title in 2008). He wasn't modern-day Kyle Korver, but was a premier 3-point shooter who would provide ample spacing on the floor for a team built around Chris Bosh.

Except, Kapono never made the type of impact to justify the price. In the 2007-08 season, he did lead the league by making 48.3 percent from long range, but averaged just 18.9 minutes per game in 81 appearances. His 3-point shooting percentage declined to 42.8 percent the following season, and he was subsequently traded to Philadelphia in a deal that landed Reggie Evans in return.

Fun fact: Kapono had an invite to Warriors training camp this season, but didn't make the team. Almost could have been a third Splash Brother.

A year before Bosh would hit unrestricted free agency, this was considered a huge coup for the Raptors when Turkoglu basically reneged on an agreement with the Portland Trail Blazers and instead signed on to be the second star next to Bosh.

Turkoglu was coming off a career season in Orlando, in which he and Dwight Howard helped lead the Magic past the Cavaliers in the Eastern Conference finals before falling short to the Los Angeles Lakers in their bid for a championship.

The problem was that Turkoglu appeared to have been more content with cashing in on his contract than contributing on the court, highlighted by an incident during the season in which he missed a game due to a stomach virus, but was seen partying in Yorkville afterwards, leading to a benching and a fine from the team. The Raptors would miss the playoffs, Bosh would leave for Miami, and Turkoglu would go to the Turkish press to say that "he had lost enthusiasm for the city" and did not want to return.

The Raptors would comply with his wishes and sent him to Phoenix that offseason. Even after his departure, Turkoglu did not stop criticizing the city and the organization.

Landry Fields' contract just expired after this most recent season, and he went from occasional contributor, to potential defensive answer to Joe Johnson in the playoffs, to permanently stuck to the bench during his three seasons in Toronto.

That's the thing with role playrs, if they're signed to some exorbitant amount (and in this case, relatively speaking, Fields was), their lack of performance becomes a permanent dent on their record.

The strangest part of all this is that the entire offer sheet the Raptors threw at Fields in the summer of 2012 was to prevent the Knicks from engaging with a sign-and-trade with the Suns to acquire Steve Nash, whom the Raptors were courting and were believed to be frontrunners to land the Canadian at the cost of a three-year, $36 million deal (which, given how Nash's health deteriorated in his final years in the league, would have landed up on this list, all Canadian-kid-returns-home vibes aside).

The Raptors were essentially paying a $20 million price in order to clear the way for Nash to come home. Instead, he chose the Lakers, and Toronto was left with another unpleasant contract.