If you could go back into Jays history and undo one trade, which one would you choose?

Nov. 1999

Blue Jays trade Shawn Green with Jorge Nunez to the LA Dodgers for Raul Mondesi and Pedro Borbon

Shawn Green was one of my favourites in the post-Gillick era. His development as a player was one of the 'classic' cases where he was able to steadily improve from year-to-year; as a fan I found it was very gratifying to watch. Apart from his offensive abilities (if memory serves), Green was also a competent defensive RF and was threat on the base paths. It made Green one of the more complete players on the late 90's teams. This culminated in the 1998 season, when he became one of the few Blue Jays to achieve the 30hr / 30sb distinction. When we traded him in Nov. 1999, he came off a season where his wRC+ was 142.

Meanwhile the guy we received was Raul Mondesi. He played for a few seasons with the Blue Jays and turned out to be just okay, not great, not spectacular (wRC+ was in the 110 range). As for Jorge Nunez and Pedro Borbon, they turned out to be players of insignificant consequence. Eventually Mondesi was traded to the Yankees for a relief pitcher (also of insignificant consequence) at the 2002 trade deadline.

I pretty much hated this trade because I loved Shawn Green. I felt that the trade was pretty one-sided, and to compound matters further, Green continued to prosper with the Dodgers (wRC+ in the 130 range over 5 seasons).

For those who too young to relate to the Delgado/Green duo, think of the JB/EE duo; it felt exactly the same way. Of course, there are few differences, namely (1) Delgado and Green were both home grown players and (2) Gord Ash broke up the combo before we could fully reap the benefits.

Post Script:

- Shawn Green actually requested to be traded to a West Coast team after the 1999 season

- Shawn Green was due for free agency after the 2000 season

- Shawn Green quickly signed a 6yr/$84mm extension with the Dodgers; something the Blue Jays could not afford

- the late 90's was a time when the Toronto Blue Jays franchise was bleeding money

- eventually the team sold to Rogers' Communications for $120mm in Sept. 2000

IIRC the late 90's was a time where sports franchises from the Big 4 were routinely losing money. This was before revenue sharing was implemented so whatever profits/losses was kept specifically to the individual team. I think football (NFL) was the only exception.