Sometimes, making a bold trade at the right time can help transform a MLB franchise into an instant contender. Other times, making it at the wrong time can help set a franchise back for many years. That is exactly what happened to the Toronto Blue Jays around this very same time of the year during the 1996-97 offseason.

At the time, the Blue Jays surprisingly dealt first baseman John Olerud to the New York Mets for pitcher Robert Person in what turned out to be a lopsided deal when all was said and done. In fact, many could debate that it has now become one of the worst trades ever in Blue Jays history.

Reliving one of the worst trades in Blue Jays history this week

Many will remember Olerud as being a huge part of the Blue Jays’ World Series contending years in 1992 and 1993. In particular, the star first baseman flirted with hitting .400 during his stellar 1993 campaign, where he ended up leading the American League in batting average (.363) and OPS (1.072) while registering 24 home runs and 107 RBIs in 158 games played.

From there, Olerud would go on to become a mainstay for the Blue Jays at first base, up until the eventual arrival of top prospect Carlos Delgado. When Delgado eventually needed a transition to first base as the physical demands of being a catcher was affecting his ability to maximize his power and effectiveness, it inadvertently created a logjam at first. Olerud supposedly could move into the designated hitter’s role, but with veteran outfielder Joe Carter already there, the preference was to keep Carter over Olerud. 

As a result, Olerud was forced into becoming expendable during December of 1996, paving the way for his move to the Mets. Looking to strengthen their pitching staff, the Blue Jays hoped that Person could become a viable option for their back end of the rotation.

However, not only would he eventually be relegated to the bullpen, the right-hander would also disappoint for the most part during his three-year tenure with the club. Person would post a dismal 8-13 record, 6.18 ERA, 1.55 WHIP, giving up 122 earned runs with 97 walks and 142 strikeouts in 177.2 total innings pitched. The Blue Jays mercifully waved the white flag and traded him to the Phillies in 1999 for pitcher Paul Spoljaric.

Olerud would continue to perform at an above average level for quite some time. He would produce 90+ runs, 20+ home runs and 100+ RBIs in seven seasons with the Mets and Seattle Mariners while batting close to .300 in the process. To add insult to injury, he would even develop the other side of his game in the field as he evolved into an elite defensive first baseman, taking home Gold Glove honours a total of three times.

Olerud eventual had stints with the New York Yankees and Boston Red Sox later on, helping lead the teams he played on to five postseason appearances between 1999 and 2005. As for the Blue Jays, they would not see even a hint of the playoffs until another decade after that.

In hindsight, had the Blue Jays chosen to keep the young Olerud and let the sentimental veteran fan favourite Carter go, things might have turned out differently. After all, Carter may have racked up many accolades during his time with the organization, but he ultimately stayed for just one more season in 1997 with Toronto before leaving for free agency.

Olerud could have teamed up with Delgado and Shawn Green to form a three-headed lefty monster lineup with the next generation of Blue Jays players at the time. Instead, it would take almost 19 more years before Toronto and their fans would see their return to the postseason, a devastating reminder that sometimes the best trades are the ones you don’t make.