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.

The Cooperstown career of Fred McGriff began in Toronto (well, in the Yankees organization, before they traded him as a Minor Leaguer in 1986, appearing in three Games, but the First Baseman appeared in 107 Games the year after, blasting 20 Home Runs, and proving himself as a capable Major League power hitter.

Entering 1988, “The Crime Dog” was now one of the better First Basemen in the AL, and he broke out with a 34 Home Run/82 RBI season.  1989 was his best year in a Blue Jays uniform, winning the Home Run (36) and OPS Title (.924) with a Silver Slugger and All-Star Game appearance.  McGriff was also sixth in MVP voting. 

After another good year in 1990, McGriff was traded to San Diego, leaving behind 130 Home Runs.  The Jays would win the 1992 and 1993 World Series, but McGriff got his rig shortly after in 1995 as an Atlanta Brave.

In 2023, McGriff was chosen by the Veteran’s Committee for the Baseball Hall of Fame.

In the glory days of the early 90s Blue Jays, Devon White was their leadoff man, helping them win their coveted back-to-back World Series Titles in 1992 and 1993.

White first tasted Major League action in 1985 as a member of the California Angels and was a starting Centerfielder two years later.  White made his first All-Star Game in 1989, but after a sub-par 1990, White was traded to Toronto in a transaction that history favored the Blue Jays.

White’s first three years in Toronto were fantastic.  A Gold Glove recipient in all five of his Jays years, White led the AL in Total Zone Runs in 1992 and Defensive bWAR and was a crucial cog in the Jays World Series wins in 1992 and 1993, the latter of which was an All-Star year.  In all those campaigns, White had at least 155 Hits, 15 Home Runs, and 30 Stolen Bases, but as competent as he was with his bat, he was considered the best defensive Centerfielder in the American League.  

White slipped in 1994 and 1995, though he was still good, he left for the Marlins for the 1996 Season via free agency.  With Toronto, White batted .270 with 733 Hits and 126 Stolen Bases.