Blue Jays: 10 stars the club missed out on that would've changed franchise history

Jon Lester

During the 2014 offseason, it was reported that the Jays had offered Jon Lester a five-year, $125 million contract. Lester was just coming off an All-Star season in which he also finished fourth in AL Cy Young voting as well. The Jays’ starting rotation at the time was led by Marcus Stroman, R.A. Dickey, and Mark Buehrle, so adding an ace-calibre starter in Lester would have solidified their rotation to make them strong contenders from the start of the 2015 season and the years beyond. But Lester at the time was looking for more term and eventually settled with a six-year deal with the Chicago Cubs.

Had the Blue Jays landed Lester to start the 2015 season, they may not have ended up needing to empty the prospect cupboard to acquire David Price and others to make the successful playoff push that they eventually had. In doing so, the Jays remained competitive for that year and the following year in 2016, but ultimately the moves led to their dismantling starting in 2017. But if you look at it in the bigger picture, we might not have Vladimir Guerrero Jr., Bo Bichette, and others now if that did not happen, so at least it helped establish our current team makeup, even though the Jays had to endure a few rebuilding years in doing so.