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The DeRozan deal takes it place in Toronto sports history among these 12 massive trades

Roger Clemens pitches for the Blue Jays in Toronto on June 21, 1997.

Frank Gunn/The Canadian Press

The blockbuster deal that saw the Toronto Raptors send all-star guard DeMar DeRozan to the San Antonio Spurs for 2014 NBA Finals MVP Kawhi Leonard is one of the biggest in the city’s history. Here are 12 other major trades that had a big impact on Toronto’s sports scene:

1968 — Maple Leafs trade Frank Mahovlich in a package to Red Wings for Norm Ullman and others

A season after beating the Montreal Canadiens in six games to win the Stanley Cup, the Maple Leafs traded struggling forward Frank Mahovlich, along with Pete Stemkowski, Garry Unger and the rights to Carl Brewer, to Detroit for Paul Henderson, Floyd Smith and Doug Barrie. Nicknamed the “Big M,” Mahovlich was an impressive mix of size, speed and talent, but he struggled with the pressure of playing in hockey-mad Toronto. Mahovlich’s career rebounded in Detroit before he went on to become a star in Montreal, helping the Canadiens win two Stanley Cups. Ullman put up good offensive numbers in Toronto, but the Maple Leafs won just one playoff series in seven-plus seasons while he was there.

1990 — Blue Jays trade Fred McGriff and Tony Fernandez to Padres for Joe Carter and Roberto Alomar

Toronto’s back-to-back World Series titles in 1992 and 1993 were built on the foundation of this trade that saw Tony Fernandez – a three-time all-star at that point – and heavy-hitter Fred McGriff sent to San Diego. In return, they got slugger Joe Carter and second baseman Roberto Alomar, who became superstars playing in Toronto. Carter’s home run in Game 6 of the 1993 World Series became the stuff of legend, while Alomar put together a Hall of Fame career. Both players are now enshrined in the Blue Jays’ Level of Excellence.

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1992 — Maple Leafs get Doug Gilmour in 10-player deal with the Flames

An off-season salary dispute ahead of the 1991-92 season soured Doug Gilmour on Calgary. He requested a trade, then walked out on the Flames on Jan. 1, 1992. The next day, Calgary dealt Gilmour to Toronto as part of a 10-player swap, the largest trade in NHL history. Gilmour, Jamie Macoun, Ric Nattress, Kent Manderville and Rick Wamsley were sent to Toronto in exchange for Gary Leeman, Craig Berube, Michel Petit, Alexander Godynyuk and Jeff Reese. Gilmour brought the Leafs back to relevancy, leading them to back-to-back conference finals in his first two full seasons with the team. He was inducted into the Hall of Fame in 2011.

1993 — Maple Leafs acquire Hall of Famer Dave Andreychuk, Daren Puppa and a first-round pick from Sabres for Grant Fuhr and a fifth-round pick

Dave Andreychuk had already scored well over 300 goals in 11 seasons with the Buffalo Sabres when Toronto traded for him. Like Gilmour before him, Andreychuk transformed the Maple Leafs into a contender that pressed for a Stanley Cup. The first-round pick Toronto got in the deal became defenceman Kenny Jonsson. Fuhr underperformed in Buffalo, eventually losing his spot in net to Dominik Hasek. Andreychuk, Fuhr and Hasek all wound up in the Hall of Fame.

1993 — Argonauts get quarterback Tracy Ham in a 16-player trade with Eskimos

The Toronto Argonauts thought they made a winning move in 1993 when they swung a 16-player deal with the Edmonton Eskimos that had future CFL Hall of Fame QB Tracy Ham as the deal’s centrepiece. Ham, who was the first quarterback in league history to rush for more than 1,000 yards in a season, passed for 3,655 yards and ran for 655 yards despite being injured for much of Edmonton’s 1992 season. The next year in Toronto, he threw for only 2,147 yards and ran for 605 and the Argonauts managed only a 3-15 record. The Eskimos went on to win the Grey Cup.

1994 — Maple Leafs get future captain Mats Sundin for former captain Wendel Clark

Although Wendel Clark had been a fan favourite in Toronto, wearing the captain’s “C” for years, injuries had slowed him down by the end of the 1993-94 season. The Maple Leafs sent Clark to the Quebec Nordiques in the off-season for Mats Sundin, Garth Butcher, Todd Warriner and a 1994 first-round draft pick. Quebec got Clark, Sylvain Lefebvre, Landon Wilson and a 1994 first-round draft pick. Sundin’s Toronto debut was delayed by the 1994-95 lockout, but when he finally arrived he impressed. He eventually succeeded Doug Gilmour as team captain and became the highest scoring player in Leafs history, earning his spot in the Hall of Fame.

1998 — Disgruntled Damon Stoudamire traded by the Raptors to the Portland Trail Blazers

Although Damon Stoudamire was the Raptors’ first-ever draft pick in 1995, he was unhappy in Toronto by early 1998. In response, he was dealt with Walt Williams and Carlos Rogers to Portland for Alvin Williams, Kenny Anderson, Gary Anderson and three picks. Kenny Anderson was flipped days later to the Boston Celtics in a move that brought future all-star Chauncey Billups as well as Roy Rogers, Dee Brown and John Thomas to Toronto.

1998 — Charles Oakley joins Raptors, Marcus Camby goes to Knicks

Young phenoms Vince Carter and Tracy McGrady needed the steady guidance of a veteran, so in 1998 the Raptors traded promising centre Marcus Camby to the New York Knicks for Charles Oakley. Known for his hard-nosed play and gruff demeanour, Oakley had a wealth of playoff experience with the Chicago Bulls and Knicks and helped Toronto win its first ever playoff series – a best-of-five victory over the Knicks in 2001. Camby went on to back up Hall of Famer Patrick Ewing in New York and had a solid career himself.

1999 — Blue Jays trade Roger Clemens to Yankees for David Wells, Homer Bush and Graeme Lloyd

Roger Clemens was dominant in his two seasons with the Blue Jays, winning the Cy Young Award both years after leading the American League in wins, strikeouts and earned-run average. However, he believed that Toronto was going to struggle in the upcoming 1999 season, so he asked to be traded to a contender. He got his wish that off-season, with David Wells, Homer Bush and Graeme Lloyd coming to the Blue Jays from the Yankees. Clemens won the World Series with New York in 1999 and 2000. Wells had a 37-18 record in two-year second stint with Toronto.

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2004 — Unhappy Vince Carter traded by Raptors to New Jersey for package including unhappy Alonzo Mourning

The dynamic Vince Carter was beloved in Toronto over his first six seasons with the Raptors. But after general manager Glen Grunwald and the entire coaching staff were fired after the 2004 off-season, Carter had friction with Raptors president Richard Peddie, newly hired GM Rob Babcock and head coach Sam Mitchell. Carter was often benched by Mitchell in the fourth quarter to emphasize a new team philosophy and the two actually got into a wrestling match in a training room. Carter was traded to New Jersey in late 2004 for Alonzo Mourning, Aaron Williams, Eric Williams and two first round draft picks. The deal was a disaster for Toronto, as Mourning never reported to the team. Carter was booed by Raptors fans for years afterwards.

2012 — Blue Jays drastically retool in deals with Florida Marlins and New York Mets

Late 2012 was a busy period for Blue Jays general manger Alex Anthopoulos, who swung two franchise-altering deals in the span of a month. On Nov. 19, he sent Jeff Mathis, Adeiny Hechavarria, Henderson Alvarez, Yunel Escobar, Jake Marisnick, Anthony DeSclafani and Justin Nicolino to the Marlins for all-star shortstop Jose Reyes, pitchers Josh Johnson, Mark Buehrle, catcher John Buck and utility infielder Emilio Bonifacio. Anthopoulos then dealt Buck as well as prospects Travis d’Arnaud, Noah Syndergaard and Wuilmer Becerra to the Mets for knuckleballer R.A. Dickey, and catchers Josh Thole and Mike Nickeas. The trades failed to make an impact in Toronto, while Syndergaard became an ace for the Mets.

2014 — Blue Jays get future MVP Josh Donaldson from Athletics for Brett Lawrie, Kendall Graveman, Sean Nolin and Franklin Barreto

Alex Anthopoulos struck again two years later, getting all-star third baseman Josh Donaldson from the Oakland Athletics for infielder Brett Lawrie, pitchers Kendall Graveman and Sean Nolin, as well as shortstop Franklin Barreto. Donaldson hit the ground running the following season, leading all vote-getters to make Major League Baseball’s all-star game and eventually being named AL MVP by the end of the season.

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