David Wells was not the best Pitcher in most of the staffs he appeared on, but the man known as "Boomer" was often the most known.

The Blue Jays released Wells in 1993 before the season started, but he gradually got better and became one of Baseball's most potent lefthanded starters.  Wells began his career with the Blue Jays, with the first strictly in the bullpen.  The southpaw split his next three years as a starter and reliever and won a World Series Ring with Toronto but saw limited action in the playoffs.

Roger Clemens wanted to play for a contender, and Wells, who was in New York, was traded to the Jays as part of the deal.  In his second run with Toronto, Wells won 37 Games in two seasons, including 20 that led the AL in 2000.  That year, Wells was an All-Star and was third in Cy Young voting, despite a 4.11 ERA, but it was a hitter’s era.

The still-struggling Jays traded Wells to the White Sox after 2000, and with the Blue Jays, he went 84-55 with 784 Strikeouts.  

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?