With the trade deadline now just days away, the Toronto Blue Jays appear to be gearing up to be sellers this season, it’s essential to examine the options available come deadline day. When evaluating division trades, Toronto has made quite a few with its American League East opponents over the 50 years of Blue Jays baseball. In honour of 50 years let’s look back at a few of the notable trades.

The Yankees and Blue Jays have actually made quite a few moves over the team’s history. One of the most notable ones was when the Yankees acquired David Cone on July 28, 1995, in exchange for Mike Gordon, Jason Jarvis, and Marty Janzen. Cone went on to win four more World Series championships in New York in 1996, 1998, 1999, and 2000, while also becoming a two-time All-Star in the Bronx. As for who the Jays got back, Marty Janzen was the only player to play games for the Jays, but ended up finishing his professional career playing in Korea and China, respectively.

The two most recent trades involving the Jays and Yankees came in 2018, when the Yankees acquired J.A. Happ from the Blue Jays on July 26, 2018, in exchange for Billy McKinney and Brandon Drury. Happ played in 51 games for the Yankees and put up a 4.13 ERA, while McKinney and Drury both struggled in Toronto and ended up leaving after the 2020 season. Drury went on to have some great seasons with the Reds and Angels, but has not played since 2024. McKinney has also not played since 2025 with the Texas Rangers.

The Red Sox and Blue Jays are most known for the trade where Danny Jansen played for both teams simultaneously (technically). The trade where Jansen was sent to the Red Sox in 2024 was before both teams had to resume a rain-delayed game back on June 26, 2024. Fun statistic aside, Jansen was traded on July 27, 2024, in exchange for prospects Cutter Coffey, Eddinson Paulino, and Gilberto Batista. Jansen only suited up for 30 games in Beantown, where he hit only .188 with three home runs and six RBIs to his name.

The trade that ends up sticking out more was when the Blue Jays traded Steve Pearce to Boston on June 28th, 2018, for Santiago Espinal. Both teams benefited from the move, as Pearce went on to win the World Series MVP in 2018 as a part of the Red Sox. Espinal, on the other hand, ended up becoming an All-Star second baseman for the Blue Jays in 2022. He was later traded to Cincinnati in 2024 for Chris McElvain.

Baltimore and Toronto have never really made trades over the histories of both franchises, but the Juan Guzman trade in 1998 was quite interesting to look back on. Guzman was traded to the Orioles on July 31, 1998, for Shannon Carter and Neiro Rodriguez. After winning back-to-back World Series in Toronto in 1992 and 1993, Guzman only played in 32 games for Baltimore, posting a 4.20 ERA across 188.2 innings of work. Guzman was later traded to Cincinnati one year to the day of being traded to Baltimore.

As for the Blue Jays, Shannon Carter never played for the team, while Neiro Rodriguez played in nine games in Toronto, posting a 10.45 ERA. He was waived in 2000 and claimed by the Mets before finally retiring in 2006.

The Blue Jays and Rays hardly ever make deals. In the history of both teams, only minor transactions seem to be the norm between the two clubs. However, when evaluating the last big move between the two clubs, it has to date back to when the Jays traded away utility man Eric Sogard to Tampa on July 28, 2019.

Sogard was coming off a career year with the Jays, where he had an .840 OPS across 73 games. He had a career high in home runs (10), RBIs (30), and was actually third on the team in WAR behind fellow infielders Freddy Galvis and Cavan Biggio. Sogard was traded for minor-leaguers Curtis Taylor and Edisson Gonzalez. Neither of whom ended up playing a game for the Blue Jays.