Looking back at the worst free-agent signings in Raptors history

Michael Grange joined Sportsnet Central to talk about the reasons for optimism in the Raptors re-signing Kawhi Leonard, and how the team would recover in the event that their star player leaves town.

The NBA’s free agency window opens this weekend, and with teams from across the Association fighting for the opportunity to open their wallets to land a coveted star or that so-called missing piece, here’s betting plenty of teams and their fanbases wind up looking back with regret.

That’s the nature of the beast, in which over-eager front offices, injuries, and a million other factors can lead to more airballs than swishes when it comes to free agency.

Longtime fans of the Toronto Raptors franchise know this all too well — the team hardly has a stellar history when it comes to free agency.

Granted, the Raptors were often treading uphill when it came time to luring free agents to the city. Misperceptions of the Toronto market and a status as a perennial loser were major factors working against the team.

You’d think the Raptors title run likely changed all of that — and within the next two seasons the team has the opportunity to find out. But those misnomers and all-too-familiar complaints apparently still exist. Just take a look at what former Raptor Lou Williams said this week:

Toronto has often been behind the eight-ball as a competitor on the open market. It’s led to overpaying and betting on role players to grow into far more when handed a starting job; When the team has tried to make a splash in the past, it’s often backfired.

While the Raps have succeeded on the trade market — the team’s leaders, Kyle Lowry and Kawhi Leonard, are proof of that — free agency hasn’t always been Toronto’s friend.

This summer, save for the potential re-signing of Kawhi Leonard, the Raptors don’t figure to have the cap room to be aggressive in free agency — it means no risk of making big-money mistakes that can set the franchise back. But as they look to address roster needs through free agency, we’ll see if team has learned from these past mistakes.

You’ll notice a theme among the players listed below. For one, many succeeded one another as an “answer” for a position of need, and, secondly, most of these signings were more or less heralded at the time, only to be deemed regrettable as the years passed.

Here are the worst free agent signings in Raptors history:

Landry Fields

Signed: 2012
Contract: Three years, $18 million

The Raptors needed a starting small forward — get used to reading that line — and whether through the draft (Joey Graham, Terrence Ross) or the trade market (Shawn Marion, Hedo Turkoglu), the team had failed to find or develop one.

Enter: Landry Fields, an unheralded second-round pick out of Stanford who enjoyed a breakout season or two with the New York Knicks in which he was probably best known for being Jeremy Lin’s buddy during the Linsanity era.

Was Fields the Raptors’ answer, or merely a pawn in Bryan Colangelo’s larger game? Definitively, the latter.

The goal in the 2012 off-season was to sign free-agent point guard Steve Nash and bring the Captain back to Canada. The Knicks were considered favourites to land the future Hall-of-Famer, and so Colangelo dipped into his bag of tricks.

By signing Fields, the plan went: Colangelo took the negotiating power away from the New York Knicks, taking away a valuable sign-and-trade asset New York could have used to create cap space to sign Nash.

So, what happened? Nash signed in Los Angeles, and the Raptors were stuck with Fields for what was then a not-insignificant cap hit of $6 million per year. Fields battled injuries and seemed to regress as a player. He averaged 3.3 points per game in 107 appearances for Toronto from 2012-15 and then, when his contract expired, was out of the NBA entirely.

Jason Kapono

Signed: 2007
Contract: Four years, ~$20 million

After a successful stint with the Miami Heat, Kapono came to Toronto with bonafide credentials — he was in the three-point contest, and won!

Kapono was another “answer” at small forward, one who would, on paper, stretch the floor to create space for Raptors star Chris Bosh while boosting the offence with his long-range shooting.

He did that, leading the NBA in three-point percentage (48.3) during his first season in Toronto. But he was a liability in just about every other area of the game and saw his minutes gradually drop as he took a role coming off the bench.

Believe it or not, it was exciting news that the Raptors were able to draw a notable free agent to the city, but the good vibes eroded quickly. Fun fact: Kapono played 3,361 minutes in a Toronto uniform and somehow never blocked a single shot.

DeMarre Carroll

Signed: 2015
Contract: Four years, $60 million

After cups of coffee with the Memphis Grizzlies, Houston Rockets, Denver Nuggets, and Utah Jazz, Carroll blossomed during two seasons with the Atlanta Hawks. As part of a potent starting five, Carroll and the Hawks finished as the first seed in the Eastern Conference with the small forward establishing himself as an effective defender who could stretch the floor on the other end of the court.

He was the exact type of player the Raptors had been coveting seemingly forever, having auditioned a revolving cast of potential three-and-D starting small forwards over the years.

Carroll had opened eyes around the NBA with a respectable defensive showing against LeBron James in the playoffs, and was pegged as a bonafide starter and prized catch on 2015’s free agent market.

He signed with Toronto and was heralded as a valuable missing piece and a key part of solving the Raptors’ post-season puzzle. Instead, his tenure was marred by injury. He was hurt six games into his first season in Toronto and a bruised knee held him to just 26 appearances in total.

He was never the same player once he returned, seemingly hesitant to re-injure himself as his role diminished. Carroll was benched by the time the Raptors were being swept by Cleveland in the 2017 playoffs, playing just 10 minutes total during the final two games of what would be his final season.

Hedo Turkoglu

Signed: 2009
Contract: Five years, $53 million

Technically a sign-and-trade, the Raptors acquired Turkoglu fresh off a Finals run with the Orlando Magic in which the sweet-shooting Turk proved to be a pivotal difference-maker.

Make no mistake: acquiring Turkoglu was considered a major coup for a Raptors franchise with no track record of attracting star talent, but had landed a player the entire basketball world had just watched excel on the playoff stage.

What’s more, there was an important role in place for him as a go-to secondary scorer and versatile 6-foot-10 playmaker alongside Bosh.

What followed was nothing short of a disaster. Turkoglu seemed unmotivated – remember the time he reportedly called in sick to work and then was spotted at a nightclub the next day? — and wasn’t interested or able to impose that winning pedigree to a young, developing Toronto roster.

By March of his first season, he was benched, a healthy scratch for the first time in four years, and soon made it clear he wanted out of Toronto — a feeling that was no doubt mutual.

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