Shannon Stewart's MLB career began with the Blue Jays in 1995, after their back-to-back titles, but still, an era where the SkyDome was rocking.

Stewart worked his way to starting at Center in 1998, swiping 51 bases with a .279 Batting Average.  His basepath acumen dipped afterward, but Stewart batted over .300 for the rest of his four-and-a-half years in Toronto and showed good power with six straight 10-Home Run years.  

The Blue Jays were no longer a contender in the early 2000s, and Stewart was traded to Minnesota for their playoff run.  Stewart collected 1,082 Hits, and batted .298 with 74 Home Runs with 166 Stolen Bases for Toronto.

Ernie Whitt was in the Red Sox organization when the Toronto Blue Jays were formed, and they used one of their Expansion picks to take the Catcher, who would appear in 23 games for the parent club that year.

Whitt's ascension was slow, playing only 2 Games for the Jays in 1978 and zero in 1979, but the decade of the 1980s was Whitt's time to shine behind the plate.  After becoming the primary Catcher in 1980, Whitt often was in a platoon situation as a Jay against right-handed Pitchers, which granted him the heavier load.  

A favorite of Blue Jays' ace Dave Stieb, he had the opportunity to catch him in his lone All-Star appearance in 1985.  That was the season when Whitt and Jays made their first post-season appearance.  Whitt also collected over 100 Hits for the first time and would accomplish that in the next five years while also having a nine-year run of 10-plus Home Runs.  

Whitt was traded to make room for younger Catchers, and when it was all said and done, the popular player managed 888 Hits with 131 Home Runs.  He is also a member of the Canadian Baseball Hall of Fame.

Vladimir Guerrero Jr., the son of Hall of Famer Vladimir Guerrero, embarked on his professional baseball career bearing the significant generational expectations that could easily undermine a less promising prospect. Signed from the Dominican Republic as an international free agent in 2015, his formidable batting ability accelerated his progression through the minor leagues, culminating in a highly anticipated Major League debut in 2019. He met these expectations by demonstrating the raw bat speed and considerable power reflective of his father’s legacy, finishing sixth in the American League Rookie of the Year voting and establishing himself as a key figure for the franchise's future.

Following his demonstration of capability during the abbreviated 2020 season, Guerrero delivered a historic, MVP-caliber performance in 2021 that would have likely earned him the award in nearly any other year, had it not been for an exceptional two-way season from Shohei Ohtani. By securing the esteemed Hank Aaron Award and his inaugural All-Star selection, the young first baseman dominated American League pitching by leading the league in runs (123), home runs (48), on-base percentage (.401), slugging percentage (.601), and achieving an impressive 1.002 OPS. This season served as a definitive statement of his elite status as a tier-one superstar, fully capable of dominating a game.

The ensuing two seasons brought a period of offensive recalibration, proving that even generational talents have to adjust to the league's counterpunches. While his power numbers dipped in 2022 and his OPS slid below .800 in a frustrating 2023, Guerrero adjusted by shoring up his defensive profile, capturing a Gold Glove at first base to show his value wasn’t strictly tied to the batter's box. The true roaring return to form arrived in 2024; shaking off a sluggish spring, he exploded down the stretch to hit a blistering .323 with 30 home runs, a surge that secured his fourth consecutive All-Star appearance and a sixth-place finish in the MVP voting.

Any anxiety regarding his long-term future in Canada was permanently erased in April 2025, when the Blue Jays front office orchestrated one of the most monumental moments in franchise history. Rather than letting their homegrown superstar walk into a high-stakes free-agent market, Toronto locked him up with a staggering 14-year, $500 million contract extension. The megadeal, featuring a full no-trade clause and no opt-outs, completely reset the organizational clock, ensuring that the face of the franchise would carry on his legacy north of the border as a lifelong Blue Jay.

With his financial future secured, Guerrero went out and validated every single penny during a thrilling 2025 campaign that culminated in a deep, magical postseason push. He put the entire team on his back in October, capturing ALCS MVP honors and absolutely tearing through the playoff brackets with a scorching 1.289 OPS and 8 postseason home runs. Though the Blue Jays ultimately fell just one victory short of a title, losing a heartbreaking 11-inning thriller in Game 7 of the World Series to the Los Angeles Dodgers, Guerrero’s absolute supremacy under the highest stakes solidified his reputation as a big-game destroyer.

Entering the 2026 season, Vladdy has the goods to enter the top five of this list by year’s end.  Could he make it all the way to the top?

Although Tom Henke had the nickname of the "Terminator," he looked more like an accountant, that is, until he pitched.

The reliever was plucked from the Rangers in 1985 as a Free Agent compensation pick.  Henke had the velocity but not the accuracy, but he had a turnaround in the minors in 1985, was called up for Toronto's playoff drive, and never looked back.

Henke, who had 13 Saves for the Blue Jays in '85, had 27 in 1986, and it looked like, after a decade of existence, Toronto finally had their closer.  His best season in a Toronto uniform was arguably in 1987 when he went to the All-Star Game and led the American League in Games Finished (52) and Saves (34).  Toronto continued to build a bona fide contender, and with Henke in tow, they did not have to worry about the 9^th Inning.  

From 1988 to 1992, Henke continued to be one of the top Relief Pitchers in the AL, recording at least 20 Saves each year, while the team had Duane Ward emerge as the 8^th-inning setup man.  The dangerous combination helped win the Blue Jays the 1992 World Series, but that would be Henke's last game in Toronto, as he signed with Texas, his original team, as a Free Agent.

As a Blue Jay, Henke compiled 217 Saves, 386 Games Finished, and had an SO/9 of 10.3.  Henke was also inducted into the Canadian Baseball Hall of Fame.