Willie Upshaw was taken from the Yankees organization via the Rule 5 Draft, with the Blue Jays hopeful that he would be the First Baseman of the future, and by 1982, four years after, he was their starter. 

Upshaw was one of Toronto’s building blocks, and he had three straight 150 Hit years, the first two where he belted over 20 Home Runs.  His best season was in 1983, where he had career-bests in HR (27), Hits (177), RBI (104), and the Slash Line (.306/.373/.515) and received votes for the MVP, finishing 11^th.  Upshaw could not reproduce that year but was a large part in getting them to their first playoff in 1985.  He played three more years in Toronto before Cleveland bought his contract.

Upshaw’s offensive numbers look like he should be higher, but First Baseman generally are better producers, which hampers his rank a little.

One of the few Canadians to play for a Canadian team, Paul Quantrill's hometown was London, Ontario, two hours away from Toronto.  The Pitcher played collegiately at the University of Wisconsin and then professionally for the Red Sox and Phillies before the latter traded him to Toronto after the 1995 Season.

Quantrill's first year with the Blue Jays was dismal, going 5-14 with a 5.43 ERA and going back and forth as a starter and reliever.  Going into 1997, Quantrill was assigned to the bullpen, and it was a good fit for him, as he kept his ERA low (1.94 in 1997 and 2.59 in 1998), and in 2001, he was an All-Star Middle Reliver, leading the AL in Games Pitched (80) with an 11-2 record.  

Quantrill was traded to Los Angeles after his 2001 All-Star year, leaving the Jays with 386 appearances.  He is also a part of the Canadian Baseball Hall of Fame.

Kevin Pillar was the best player at California State University, where he set a Division II school hit streak record with 54 Games.  As good as he was, Pillar still played in Division II and dropped to the 32^nd Round of the 2011 Draft, but Pillar defied the odds and first made the Blue Jays in only two years. 

Pillar entered the 2015 season as Toronto's starting Centerfielder, and he batted .278 with 163 Hits and a Wilson Platinum Glove.  The Blue Jays were contenders, with Pillar providing the occasional clutch hit.  Toronto reached the ALCS in 2015 and did so again in 2016, with a 144 Hit/.266 campaign. 

He never played another playoff game in Toronto but had two more respectable years, though his OBP was not great.  The Jays shipped him off to San Francisco early in the 2019 season, leaving Pillar with 641 Hits as a Blue Jay.

A 1991 First Round Pick in 1991, Shawn Green first made it to the Majors as a September call-up in the 1993 World Series winning season.  Green did not play in the post-season and was in the minors for most of 1994, but he was the starting Rightfielder going into 1995, a position he would keep for the rest of the decades.

Green was a middle-of-the-road starter at RF for the Blue Jays for a few years but had an elevated stat line in 1998, belting 35 Home Runs with 1000 RBIs.  That was the type of season that the Blue Jays were hoping for, but he took it to another level in 1999.

Green’s 1999 campaign was the best of his life, compiling career-highs in Home Runs (42) and OPS (.972) while obtaining an All-Star, a Gold Glove, and Silver Slugger.  The Outfielder was also ninth for the American League MVP.  This was a star-making, yea, but Toronto was not a contender and traded Green to the Dodgers after this year.

With Toronto, Green had 119 Home Runs and 718 Hits and batted .286.