13 biggest acquisitions in Toronto sports history


Toronto Maple Leafs' Doug Gilmour (93) moves the puck against Chicago Blackhawks' Patrick Poulin (44) during the first period, Saturday, April 23, 1994 in Chicago. (Tim Boyle/AP)

The Toronto Raptors made a big splash on Wednesday, acquiring former NBA Finals MVP Kawhi Leonard in exchange for fan favourite, and the franchise leader in games played and points scored, DeMar DeRozan.

It was a stunning event, the calibre of trade we don’t often see — yet it’s the second time this summer a superstar player is joining a Toronto franchise.

So where does the Leonard-DeRozan blockbuster rank in the history of jaw-dropping Toronto sports moves?

Glad you asked.

Blue Jays trade for Joe Carter and Roberto Alomar in 1990

The deal: Toronto trades Fred McGriff and Tony Fernandez to the San Diego Padres for Joe Carter and Roberto Alomar.

McGriff and Fernandez were established stars with the Blue Jays and beloved by fans, even if they failed to bring playoff success to the organization. When the veteran duo was dealt to the Padres, it signalled what was perceived as a total rebuild.

Carter came to Toronto as an established star, having averaged 109 RBIs in his five previous seasons, but Alomar was lesser known and still in the early stages of his career.

We all know what happened from there.

Argos lure “Rocket” Ismail to the CFL in 1991

The deal: Four-year, $18.2-million contract

Raghib “Rocket” Ismail was projected to be the NFL’s first overall pick, but signed a more lucrative deal with the CFL’s Argonauts — one that the Dallas Cowboys and owner Jerry Jones were unwilling to match — in a fairly unprecedented move.

Ismail hit the ground running in his first of two seasons in Toronto, posting 1,300 receiving yards and nine touchdowns as a rookie in ’91, helping the Argos hoist the Grey Cup that year.

Maple Leafs trade for Doug Gilmour in 1992

The deal: Calgary Flames trade Doug Gilmour, Ric Nattress, Kent Manderville, Jamie Macoun and Rick Wamsley to Toronto in exchange for Gary Leeman, Craig Berube, Alexander Godynyuk, Michel Petit and Jeff Reese.

Gilmour was an established commodity by ’92, having already topped 100 points in a season, and helped the Flames win the Stanley Cup in 1989. But his relationship with management had soured in Calgary, which helped Toronto swoop in and steal the forward.

In his first full season with the Maple Leafs in ’92-93, Gilmour posted a career-high 127 points and helped carry the team to back-to-back conference finals appearances. He may go down as the most popular Leaf of all-time.

Maple Leafs acquire Mats Sundin in 1994

The deal: Toronto acquires Sundin, Todd Warriner, Garth Butcher and the 10th overall pick in the draft from the Quebec Nordiques in exchange for Wendel Clark, Sylvain Lefebvre, Landon Wilson and the 22nd overall pick.

Like DeRozan, Clark was a fan favourite in Toronto. After being drafted first overall by the Leafs in 1985, he went on to help lead the Leafs to the playoffs in six of the next nine seasons, including conference finals runs in ’93 and ’94 in which he managed 36 points in 39 games.

The team pulled the trigger on the deal in the ’94 off-season, leveraging Clark’s trade value to acquire another former first overall pick in Sundin, who averaged 99.5 points during his previous two seasons.

Sundin went on to a storied career in Toronto, captaining the Maple Leafs for 11 of his 13 seasons with the team. He is the franchise’s leader in total goals (420), points (987) and game-winning goals (79).

Blue Jays sign Roger Clemens in 1996

The deal: Four-year, $40-million contract in free agency.

Clemens’ best days in Boston were well behind him by the time the Blue Jays inked the then-33-year-old pitcher. But there was no doubting his resume, which included three CY Young awards during his Red Sox tenure.

In Toronto, Clemens was rejuvenated and won the CY Young in each of his two seasons with the Jays before the team traded him to the New York Yankees.

Argonauts sign Doug Flutie in 1996

The deal: Two-year, $2-million contract

Flutie was a bona fide CFL superstar by the time he joined the Argos. He had set a then-CFL record in passing yards and was the league’s Most Outstanding Player in ’91 with the B.C. Lions. Flutie also won a Grey Cup (and MVP award) in ’92 with the Calgary Stampeders.

He didn’t disappoint during his Toronto tenure, leading the Argos to a franchise-record 15 wins in his first two seasons, taking home two more Most Outstanding Player honours in the process, and bringing two more Grey Cup victories to the city and franchise.

Maple Leafs sign Curtis Joseph in 1998

The deal: Toronto signs Curtis Joseph to four-year, $24-million deal
The Leafs were in the midst of a playoff draught when Joseph arrived, fresh off a pair of impressive playoff appearances with the Edmonton Oilers. At 31 years old and still in his prime, Joseph helped Toronto return to the playoffs in his first season with the leafs. That year, the team reached the conference finals and Joseph was named as a runner-up for the Vezina trophy.

The Leafs reached the playoffs in each of Joseph’s four seasons in Toronto.

Maple Leafs trade for Dion Phaneuf in 2010

The deal: Toronto acquires Dion Phaneuf, Fredrik Sjostrom, and Keith Aulie in exchange for Niklas Hagman, Matt Stajan and Jamal Mayers and Ian White

Almost 20 years after completing a multi-player blockbuster with the Calgary Flames, the Maple Leafs were at it again, this time picking up defenceman Dion Phaneuf in a mid-season trade.

Just 24 years of age at the time, Phaneuf already had two all-star appearances to his name with seemingly plenty more in store for the future. The former world junior standout had scored 39 power-play goals over his first three NHL seasons in Calgary, and seemed to have the makings of a legitimate first-line defenceman, even being named a first-team all-star in 2007-08.

Yet Phaneuf had already struggled in that 2009-10 season prior to the trade, and those struggles continued once he landed in Toronto. Yes, he played in the 2012 all-star game, but after scoring those 39 power-play goals in his first three seasons, Phaneuf proceeded to score just 17 in his seven seasons in Toronto before being eventually traded to Ottawa in 2016.

“If Wayne Gretzky can get traded, anyone can get traded,” Phaneuf said upon learning of the deal.

Toronto FC lands Jermain Defoe in 2014

The deal: A 6-million euro transfer fee

It was, if you recall, “a bloody big deal” when Toronto FC brought in the noted Premier League striker — the first marquee international transfer in the team’s history.

Defoe got off to a hot start, with 11 goals in his first 16 games, but struggled to stay healthy and was out of the MLS within a year.

Blue Jays’ David Price and Troy Tulowitzki deadline splash in 2015

The deals: Detroit Tigers trade David Price to Toronto for pitching prospect Daniel Norris; Colorado Rockies trade Troy Tulowitzki to Toronto for Jose Reyes

The Blue Jays made noise at the 2015 MLB trade deadline, picking up a pair of stars to help bolster the stretch run toward the playoffs. The moves paid off — Price went 9-1 in his lone season in a Jays uniform while Tulowitzki strengthened the Blue Jays lineup — and the team came the closest they’d come to a World Series appearance since ’93, reaching the ALCS.

Maple Leafs sign John Tavares

The deal: Seven-year, $77-million contract in free agency
Looking to bolster a promising, albeit young, lineup centred around first overall pick Auston Matthews, the Leafs made their biggest free agent splash in franchise history, inking Tavares to a long-term deal that will see the three-time all-star make his Maple Leaf debut in the 2018-19 season.

Raptors land Kawhi Leonard

The deal: Raptors acquire Kawhi Leonard and Danny Green in exchange for DeMar DeRozan, Jakob Poeltl and a 2019 first-round pick

The news arrived to mixed emotions from a fan base who had seen DeRozan blossom into an all-star and etch his name in Raptors franchise record books. Masai Ujiri and the Raptors’ front office took advantage of a sour situation in San Antonio that saw them forced to deal superstar swingman Leonard — the 2014 Finals MVP.

Leonard is set to make his Raptors debut in the 2018-19 season.

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