TORONTO -- From the World Series years of 1992-93 up to the postseason runs of 2015-16 and today’s club, the Blue Jays have never shied away from taking a big swing on the trade market.

There have been some misses along the way, of course, but most of the organization’s biggest moments can be traced back to the trades that built those rosters. Here’s a look back at 10 of the biggest trades in Blue Jays history:

The Big One
Blue Jays acquire from Padres: OF Joe Carter, 2B Roberto Alomar
Blue Jays trade: SS Tony Fernandez, 1B Fred McGriff
Date: Dec. 5, 1990

This deal was always viewed through the lens of what it led to -- two World Series championships -- but at the time it happened, this trade was a risky blockbuster with stars on either side. Eight years prior to this deal, the Blue Jays acquired McGriff from the Yankees as part of a package for Tom Dodd and Dale Murray, another of the club’s all-time great trades. The Blue Jays went on to win it all in ’92, though, and in ’93, Joe Carter’s famous “Touch ‘em all” home run cemented his place in Blue Jays history. In 2021, Alomar was placed on the Ineligible List following an investigation into sexual misconduct and the organization announced they would be “severing all ties” with Alomar.

Before the Bat Flip…
Blue Jays acquire from Pirates: IF/OF Jose Bautista
Blue Jays trade: C Robinzon Diaz
Date: Aug. 21, 2008

This trade didn’t lead to a championship, but has there been a deal with better value? At the time, Bautista was a 27-year-old fringe player bouncing from team to team. Two years after joining the Blue Jays, Bautista launched 54 home runs, a club record that still stands. Bautista was the face of baseball in Toronto for years, embodying the spirit of the ’15 and ’16 clubs that made playoff runs, and he’ll forever be remembered for The Bat Flip.

Dealing Doc
Blue Jays acquire from Phillies: RHP Kyle Drabek, C Travis d'Arnaud, OF Michael Taylor
Blue Jays trade: RHP Roy Halladay
Date: Dec. 16, 2009

The Halladay trade didn’t bridge eras of greatness in the way the Blue Jays hoped, but when you deal a franchise icon, it makes an impact. Halladay got his chance to make postseason runs in Philadelphia while the Blue Jays got the prospect upside they coveted, although Drabek never touched his ceiling in Toronto.

Landing an MVP
Blue Jays acquire from A’s: 3B Josh Donaldson
Blue Jays trade: 3B Brett Lawrie, INF Franklin Barreto, RHP Kendall Graveman, LHP Sean Nolin
Date: Nov. 28, 2014

This stroke of genius from then-GM Alex Anthopoulos ignited the playoff runs of ’15 and ’16, with Donaldson immediately winning the AL MVP Award upon his arrival. Donaldson’s time in Toronto was limited to three full seasons and part of a fourth, but his peak can be held up against any position player who’s ever worn the Blue Jays’ uniform.

All-in in 2015
Blue Jays acquire from Tigers: LHP David Price
Blue Jays trade: LHP Daniel Norris, LHP Matthew Boyd, LHP Jairo Labourt
Date: July 30, 2015

It’s difficult to overstate the excitement around the organization on the day this deal was made. Troy Tulowitzki had been acquired just two days prior, and by landing Price, the Blue Jays were officially all in. Part of the narrative surrounding those postseason runs is not only the talent the Blue Jays had, but how aggressive they were in acquiring it so quickly.

The Devo trade
Blue Jays acquire from Angels: OF Devon White, RHP Willie Fraser, RHP Marcus Moore
Blue Jays trade: OF Junior Félix, INF Luis Sojo, C Ken Rivers
Date: Dec. 2, 1990

The White trade was one of the most important moves the Blue Jays made to set up their World Series runs in ’92 and ’93, landing them one of the game’s most gifted defenders. White could hit and steal bases, of course, but any defender’s claim to greatness in Toronto will always be compared to White’s years patrolling center. He showed up when it mattered most, too, with some fine postseason performances to go along with his five Gold Glove Awards in five years.

Swing and a miss
Blue Jays acquire from Rangers: RHP Esteban Loaiza
Blue Jays trade: INF Michael Young, RHP Dawrin Cubillan
Date: July 19, 2000

They can’t all be good. Loaiza was 28 when the Blue Jays acquired him and the right-hander gave the club a 4.96 ERA over parts of three seasons, but losing Young will always hurt. Young went on to play 15 MLB seasons, 13 of them spent as one of the faces of the Rangers, where he made seven All-Star Games.

The blockbuster that wasn’t
Blue Jays acquire from Marlins: RHP Josh Johnson, LHP Mark Buehrle, SS José Reyes, C John Buck, INF Emilio Bonifácio
Blue Jays trade: RHP Henderson Alvarez, RHP Anthony DeSclafani, OF Jake Marisnick, SS Adeiny Hechavarría, SS Yunel Escobar, LHP Justin Nicolino, C Jeff Mathis
Date: Nov. 19, 2012

This big, complicated deal was supposed to push the Blue Jays over the top and immediately positioned them as World Series favorites. That didn’t quite work out, of course, as neither side of this deal ended up providing its projected value. Buehrle, one of the game’s most reliable pitchers, still gave the Blue Jays a 3.78 ERA over his three years in Toronto, falling just short of his 15th consecutive 200-inning season in ’15 before retiring.

The Rocket blasts off
Blue Jays acquire from Yankees: LHP David Wells, LHP Graeme Lloyd, INF Homer Bush
Blue Jays trade: RHP Roger Clemens
Date: Feb. 18, 1999

This was a major move at the time, even though it was an obvious one with Clemens wanting out. Clemens was coming off back-to-back AL Cy Young Awards in ’97 and ’98, posting a combined 2.33 ERA with 563 strikeouts over 498 2/3 innings. He’s rarely remembered among the all-time Blue Jays greats, but those two seasons stand above the rest rather easily. Wells was a familiar name, as he’d started his career in Toronto as a reliever before transitioning into a starting role. This time, he spent two more seasons with the Blue Jays, posting a 4.47 ERA.

Rolling the dice on Ward
Blue Jays acquire from Braves: RHP Duane Ward
Blue Jays trade: RHP Doyle Alexander
Date: July 6, 1986

In another risk that paid off, the Blue Jays acquired a 23-year-old Ward midway through the ’86 season for veteran Doyle Alexander, who’d won 17 games for them in each of the previous two seasons with a combined 3.29 ERA. Ward developed into one of the greatest Blue Jays pitchers we’ve seen, forming an incredible one-two punch with Tom Henke and saving 45 games in ’93.