Blue Jays: Best players in franchise history to wear jersey numbers 21-30

This article is part of a continuing series of the best players in Toronto Blue Jays history to wear each jersey number. You can read previous installments, 0-10, and 11-20. 

And now, the best players ever to wear jersey numbers 21-30.

#21 Roger Clemens

By the time Roger Clemens became a free agent following the 1996 season, his relationship with the team that drafted him, the Boston Red Sox, had soured and it also appeared that the then-33-year-old’s best days were behind him.

To the surprise of many, Clemens decided to sign with the Blue Jays, and he proved that not only was he far from being done, but he was also still perhaps the best pitcher in the sport.

In 1997, “Rocket” staked that claim by leading the American League in wins, ERA, complete games and strikeouts on his way to winning the fourth Cy Young of his career.

He was nearly as good in 1998, going 20-6 with a 2.65 ERA and 271 Ks to capture the top pitcher award once again. By the time 1999 rolled around, Clemens was unhappy (sound familiar?) and was traded to the New York Yankees.

#22 Jimmy Key

Jimmy Key is the best left-handed pitcher in Blue Jays lore and broke out in 1985 with the first of three straight 200-inning seasons. He was also named an All-Star that year and was a key contributor on a team that won 99 games and was on the precipice of the World Series.

Key’s best season was in 1987 when he led the AL in ERA (2.76) and WHIP (1.05) while throwing 261 innings and finishing second in Cy Young voting. The Huntsville, Alabama native cemented his place in the hearts of Blue Jays nation by pitching an absolute gem in Game four of the World Series, 7.2 innings of one-run ball in a game the Jays won 2-1.

#25 Carlos Delgado 

This is one of the more star-studded number groups for the Blue Jays as Devon White, Troy Glaus, and Marco Estrada all wore number 25, but the top spot goes to the most dominant slugger the team has ever seen.

Carlos Delgado came up as a catcher in the early-90s, played some outfield, and didn’t move over to first base until 1997. He had a remarkable run of power that saw the imposing infielder hit at least 25 home runs every year from 1996-2004.

Delgado’s peak career arc was from 1998 to 2003 when his average season was 39 homers and 123 RBI. He was top-five in MVP voting twice, including a second-place finish in 2003 when had a league-leading 145 RBI, and a 1.019 OPS. 

#26 Willie Upshaw

Willie Upshaw was a big part of the early-80s Jays teams that began turning things around and eventually transformed into a World Series contender. 

In 1983, the team achieved its first winning season and Upshaw was front-and-center, hitting .306 with 27 big flies and 104 RBI. He played in 160 games, had a 136 OPS+, and placed 11th in MVP voting. 

Upshaw was one of the most durable players on the Jays, averaging 154 games played between 1982 and 1987. Honorable mention to Adam Lind who ranks ninth-highest on the team's all-time home run list with 146.    

#27 Vladimir Guerrero Jr.

When the Blue Jays signed the son of Vladimir Guerrero as a teenager in the mid-2010s, it had fans salivating over what he could do with a few years of training. 

He hit a towering, walk-off homer at Olympic Stadium in an exhibition game in 2019, indicating he was close to being MLB-ready.  Vladimir Guerrero Jr. made his debut later that year, and, while he showed he was good enough for the show, there were clearly better days ahead. 

That would prove to be true. Despite a slight setback during the COVID-shortened 2020 season, Vladdy’s career has been on a stratospheric incline. His breakthrough 2021 season, when he led the AL in runs, home runs, OPS, and total bases, would have won the MVP in most years.

“Vladito” followed that up with a solid 2022 that featured his first Gold Glove award and 100th career homer. He’s already one of the most impressive players in franchise history, the exciting part is that he’s just getting started. 

#28 Shaun Marcum

Shaun Marcum was inserted into the starting rotation in June 2006 and remained a fixture through the 2010 campaign. 

He showed improvement over his first two seasons until an elbow injury led to Tommy John surgery late in the 2008 season. Marcum recovered to become the Jays' opening-day starter in 2010, ending a stretch of seven straight years that Roy Halladay filled that role. 

The former third-round pick responded by having his best season with a 13- 8 record, 3.64 ERA, and a career-best 165 strikeouts. The front office parlayed that into flipping Marcum to Milwaukee for Brett Lawrie, who was ultimately dealt to Oakland in the Josh Donaldson trade.

#29 Joe Carter

Pretty close call here really when you consider the career of Jesse Barfield, who had a great run throughout the 80s. 

If you compare their three best seasons, they stack up fairly closely. From 1985-1987, Barfield hit .280 with 290 runs scored, 95 home runs, and a .873 OPS. Joe Carter, from 1991-1993, hit .264 with 278 runs scored, 100 homers, and a .815 OPS. 

Obviously, Carter’s iconic home run to clinch the 1993 World Series is a moment that will last forever in the heart of Blue Jays fans and is enough to give him the edge here too. 

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#30 Todd Stottlemyre

Todd Stottlemyre made his debut in 1989 and became a valuable and versatile member of the pitching staff for the next six years. 

The son of former Yankees star Mel Stottlemyre, Todd made 175 starts and also 31 appearances out of the bullpen with Toronto. His best season was in 1991 when he went 15-8 with a 3.78 ERA, made 34 starts, and pitched 219 innings. 

The lasting image of Stottlemyre to many will be him gliding to third base, wearing a windbreaker, and getting tagged out a third base in the 1993 World Series. 

He did have his inconsistencies and could be wild, but Stottlemyre was fiery, fun to watch, and a fan favorite. Give it a few years and Alejandro Kirk is likely going to take this spot and hold onto it for the foreseeable future.