The Toronto Blue Jays have existed for a little bit under 50 years, joining the league along with the Seattle Mariners in 1977, but that relatively short window hasn’t stopped them from making some explosive deals with the Yankees over the years. It’s been a while since anything really huge struck, but the 19 trades or purchases between the two sides include multiple Hall of Famers and a fair share of All-Stars. Here, you’ll get to find out who they are!
July 28, 1995: The Yankee trade Mike Gordon, Jason Jarvis and Marty Janzen to the Blue Jays for David Cone .
There are a couple candidates for this category, and ultimately I’m going with this one over the 1999 deal that brought Roger Clemens to the Bronx for a few reasons. First, while Roger was the bigger star, Cone played a significant role on every team of the ‘90s championship run, perhaps the biggest of any non-Core Four plus Bernie member. Second, acquiring the Rocket did require giving up a very good player in his own right, with David Wells giving the Jays a top-three Cy Young finish a year later. The cost to acquire Cone, meanwhile, was negligible. Of the trio involved, only Janzen ever made it to the bigs, and that only for 27 games of 6.29 ERA pitching.
Part of the reason Cone was so relatively cheap to acquire — all three of them were solid but unspectacular prospects — was that he was a free agent at the end of the year, but after gong 9-3 down the stretch to secure a playoff berth after moving to the Bronx at the trade deadline in ‘95, they didn’t have much trouble retaining Coney outside of a brief flirtation with the O’s. He ultimately finished with a 64-40 win-loss record over six years in pinstripes, good for 20.3 rWAR and 18.1 fWAR. He left with his share of memorable moments, too, spinning the 16th perfect game in MLB history and shining in the playoffs, allowing just two earned runs in 19 innings over a start each in the ‘96, ‘98, and ‘99 Fall Classics.
December 9, 1982: Yankees trade Dave Collins, Mike Morgan, Fred McGriff, and cash considerations to Blue Jays for Tom Dodd and Dale Murray.
If dealing Willie McGee was an oof, this one would be classified as a mega oof. It’s easy to see why it happened, to be fair. McGriff, a 17-year-old ninth-round draft pick, had hit just .238 with nine homers and 50 driven in over 92 games of Rookie-level action in 1980 and 1981. Further up the ladder, the Yankees also had a rising star named Don Mattingly set to occupy first base for the foreseeable future. Understandably, they probably dealt McGriff without much of a second thought.
Both Dodd and Murray were close to non-factors for the Yankees. The former never reached the majors for the Yankees, later collecting 16 plate appearances for the Orioles in 1986. The latter stayed with the team until midway through the 1985 season, posting a 4.73 ERA in 62 appearances covering 120 IP. Collins produced a solid 4.6 rWAR in two years with the Jays, but Morgan didn’t do much, making just 16 appearances with the club. (He’d fare better elsewhere and survive in the majors even after the turn of the century.)
McGriff, meanwhile, took a while to reach the big leagues, establishing himself in 1987, but boy did he do it with a bang. The seven seasons he had before reaching free agency produced a whopping 38.2 rWAR and 40.4 fWAR, 12th and fifth in the majors respectively during that span. He went on to club 493 career bombs and made the Hall of Fame in 2023. It may have been an understandable deal, but it doesn’t make that sting any less. Some of those ‘80s and ‘90s Yankees teams sure could’ve used those numbers.
Most Overlooked Trade
August 4, 2018: Yankees trade cash considerations to Blue Jays for Gio Urshela.
Quite a few big names pop up on this short but interesting list, and the role of Urshela on the Yankees’ most recent run of success shouldn’t be ignored. We are trying to avoid cash-only transactions, but everyone — perhaps even the Yankees — overlooked this stunner.
Gio’s pre-Yankees tenure is typically more associated with Cleveland, with whom he played 148 games split between 2015 and 2017. But it was the Blue Jays who got the first look at him when he became a Cleveland roster casualty, suiting up 19 times for Toronto in 2018. When they claimed Oliver Drake from the Minnesota Twins in August of that year, Urshela was once again a 40-man roster casualty, and the Yankees were able to get him for as close to free as you’ll get in baseball. He got his chance in April of 2019, and over a thousand plate appearances of .292/.335/.480 hitting later, the Yankees wound up with a pretty good deal out of it.
July 26, 2018: The Yankees trade Brandon Drury and Billy McKinney for J.A. Happ.
There’s not necessarily anything super bizarre about this deal, and the rest of the teams’ dealings with each other have been relatively straightforward. Things just got a little bit weird here with everyone involved. Few would have anticipated that Drury’s stint with the Yankees would be so short. There wasn’t exactly fanfare when he arrived from the Diamondbacks in a three-team deal following the 2017 season, but it had certainly piqued some interest, as Drury was generally expected to replace the underwhelming Chase Headley at the hot corner.
That ... didn’t happen. Drury hit the IL eight games into the season, and by the time he returned two months later, Miguel Andújar had a firm grip on his start. So, just a few months later, he found himself packaged with McKinney — who, funnily enough, made his way back to the Yankees, of course — in exchange for Happ, who was on an expiring contract for an out-of-contention Jays team. Drury was ineffective for the Jays before re-discovering himself in 2022, hitting 54 homers since then, a half-decade after he missed his chance with the Yanks.
On our end, Happ was excellent down the stretch, winning seven of 11 starts with a 2.69 ERA, and both sides found a reunion mutually attractive. As you might remember, the relationship ultimately soured when Happ accused the Yankees of intentionally limiting his workload in 2020 to prevent a $17 million option from vesting, as he finished with nine starts and 49 innings when 10 starts and 62 innings would have vested the option. The ALDS snafu piggybacking Deivi García didn’t help, either. A useful trade, to be sure, but one that contained a strange kind of disappointment within it.
Other Trades of Note
November 21, 1979: Yankees trade Chris Chambliss, Dámaso García, and Paul Mirabella to Blue Jays for Rick Cerone, Tom Underwood, and Ted Wilborn.
The first player-for player deal between these two, executed two years after the Jays’ inception, this one came as a part of the team’s late-’70s remodel, losing a lineup stalwart in Chambliss after six years at first base. He never played a game for Toronto, being flipped immediately to Atlanta in a second deal, where he’d spend the rest of his career. García at least became a two-time All-Star for the Jays and a familiar presence over the next decade.
Cerone was gifted the unenviable task of replacing Thurman Munson behind the dish after the latter’s 1979 death, but he finished seventh in MVP voting with a four-win 1980 season, and played a solid part-time role in the subsequent three seasons. Underwood played his part with the team, working to a 3.77 ERA in 212 innings in parts of two seasons before being dealt to Oakland midway through the next season.
April 30, 1990: The Yankees trade Al Leiter to the Blue Jays for Jesse Barfield.
This one would merit consideration for the Worst Trade category, if it weren’t for the fact that Leiter wasn’t particularly successful for the Jays, and didn’t break out until the mid seasons of his career, six-plus years after the trade. Barfield had been a star for much of the ‘80s and delivered a few solid sub-star caliber seasons in the Bronx, hitting 60 homers with a 120 wRC+/OPS+ in his first three years before running out of steam and riding into retirement with 30 replacement games the next year. Leiter, 22 at the time of the trade, wouldn’t claim a roster spot with Toronto until 1994, and ran a 4.66 ERA in his first two seasons before a four-win walk year nearly six years post-trade set himself up for a memorable run with the Marlins and Mets in free agency.
April 30, 1990: The Yankees trade Homer Bush, Graeme Lloyd and David Wells to the Blue Jays for Roger Clemens.
The blockbuster of blockbusters, Clemens had pitched himself back into superstar territory with his two-year Cy Young stint with the Jays, and used the bounce-back to set his sights on bigger stages than the mediocre Blue Jays. Boomer had a memorable stint in the Bronx, including a perfect game and World Series MVP, but with Cone, El Duque, and Andy Pettitte holding down the rest of the rotation, he was a price they were willing to pay — along with Bush and Lloyd, who combined for 3.9 rWAR in scattered playing time with the Jays — for the addition of the then-future Hall of Famer.
July 1, 2002: The Yankees trade Scott Wiggins to the Blue Jays for Raúl Mondesi.
Just a funny little deal, executed midway through the 2002 season in a salary dump and one that shocked Toronto GM J.P. Ricciardi so much that he nearly veered off the road while taking the call. Mondesi was on the decline, but still a capable player, averaging 2.6 rWAR over his previous four seasons after being a borderline All-Star earlier in his career. Perhaps it’s notable because Mondesi was the first of what became a string of mid- or late-career veterans employed to fill the Paul O’Neill-sized hole in right field. Mondesi hit .250/.323/.450 in 169 games over two seasons, good for a 104 OPS+, but not good enough to stop him from being dealt at the deadline the next season.