If our math and calendar are correct, somebody is going to win the World Series this weekend.
It could be the Blue Jays team that is up 3-2 in the best-of-seven going into Game 6 on Friday night at Rogers Centre. They are not only on the cusp of the first Canadian crown since 1993, but they are a great story of comeback clout and camaraderie after finishing in last place in the American League East in 2024.
Or it could be the Dodgers team that still has plenty of pieces to put together two consecutive wins and become MLB’s first repeat champions since the 1998-2000 Yankees.
Whoever wins will have completed baseball’s greatest team achievement and will forever be the toast of their town.
But what about the individual legacies at stake in this World Series? Let’s take a look at some people whose career story would be most affected by a victory this weekend.
Vladdy’s 27 hits and 54 total bases in this postseason trail only the Rays’ Randy Arozarena in 2020 (29 hits and 64 total bases). And Guerrero has done this in 16 games, whereas Arozarena did it in 20. Though players these days obviously have more inventory of games than many of their predecessors, a strong finish here could give Guerrero an argument for the greatest offensive October of all-time.
After awarding Guerrero a $500 million contract earlier this year, the Blue Jays could not ask for more from him in terms of performance and presence in this postseason. They feel like he’s matured right in front of their eyes, embracing the magnitude of this moment. If they win it all here, whatever happens the remainder of that 14-year pact can’t change that.
Vladdy also has a shot at World Series MVP. All of this could one day be an important consideration when he’s eligible to become the first son to join his father in Cooperstown. And considering Vladdy Sr. never won it all, it would sure mean a lot to the family, too.
Kershaw’s legacy as a future first-ballot Hall of Famer is secure. Going out on top, though, would have extra meaning for a man who, unfortunately, was not able to participate in last year’s postseason. Kershaw was magnificent in the Dodgers’ 2020 World Series, and that definitely counts. But no one would say it looked or felt the same as doing it in a full season and relevant ballpark.
If Kershaw’s last career appearance turns out to be one key out of relief in the Game 3 epic and it contributes to a title (in his first career appearance in extra innings, no less!) that’s a pretty awesome way to end it.
Kershaw could join this very, very short list of Hall of Famers who finished their career by appearing in the World Series with a championship team:
Mad Max sure doesn’t appear prone to hanging them up after this season, and the 41-year-old has shown in this postseason that he still has something to offer a rotation. But as of today, there’s no telling what 2026 holds for him. For all we know, the same point about Kershaw and capping your career as champion might apply.
But either way, Scherzer, a member of the 2019 Nationals and 2023 Rangers, can win a ring with his third different franchise. Here’s the short list of players who have done that (requiring at least one postseason appearance for each team):
Andrew Friedman and Dave Roberts
Roberts already has the best regular-season winning percentage (.621) of any skipper with at least 1,000 games managed, and he’s been at the helm for two World Series titles. He might already have done enough to be a Hall of Fame manager, but a third title would probably clinch it for him.
Three rings would also make for a pretty strong argument for Friedman to join the short list of Hall of Fame executives. Friedman proved he can win on a meager budget in Tampa Bay. With Los Angeles, the budget is bigger, obviously, but the machine the Dodgers have maintained despite consistently picking low in the Draft is impressive. And we see plenty of examples of other big-market clubs that can’t consistently advance despite their advantages in resources.
Mark Shapiro, Ross Atkins and John Schneider
The Blue Jays’ president, general manager and manager all seemingly entered the season on iffy ground.
Shapiro and Atkins took over the front office prior to 2016, and, while that team did reach the AL Championship Series, it was mostly the previous regime’s work that had built that club. Prior to this year, the Shapiro/Atkins era was primarily marked by underachievement, with the team unable to win a single playoff game in three October appearances, including two with Schneider at the helm. Finishing dead last in the AL East last year, with their contracts winding down, made for a potentially precarious situation.
Win or lose in this World Series, the once-shaky ground is now stable ground But a victory here would only further affirm the work Shapiro and Atkins have done with the Blue Jays and the hire they made in Schneider — a member of the organization as a player, coach and manager for more than 20 years.
Having dislocated his shoulder in Game 2 against the Yankees and therefore not performed his best last year, the World Series itself was the last hill for Ohtani to conquer. Suffice to say he’s done that, having authored the greatest single-game individual offensive performance in Series history.
With a 1.395 OPS through five games, Ohtani has a chance at World Series MVP if the Dodgers win it, even though his start in Game 4 was obviously not up to his usual standard. Currently, Ohtani’s OPS ranks 17th all-time among those with at least 20 plate appearances in a World Series (Barry Bonds’ 1.994 mark with the 2002 Giants is the best). We’ll see where he finishes on that list.
The Blue Jays gave Springer their richest free-agent contract in history in part because of his postseason pedigree. At the ripe old age of 36, on the heels of a resurgent 2025 season, Springer has shown them he’s still an impact player on the biggest stage, despite a body that is, as his manager joked, “held together with duct tape” right now.
In this postseason, Springer has been plunked on the knee and the hand, and he was out of the starting lineup for Games 4 and 5 of this World Series with right side discomfort. But imagine the man tied for third all-time in postseason home runs (23) grinding through pain to hit a pivotal home run.
Has that happened before? Maybe we should ask the Dodgers.
Having already hit a walk-off homer in Game 3, Freeman is still in the mix to potentially earn the MVP honor before this Series wraps. If he does, he would be the first repeat World Series MVP.
The Blue Jays acquired the right-handed reliever at the Trade Deadline and have been riding him for all he’s worth. He’s appeared in 13 of their 16 postseason games. That gives Varland a chance at matching and perhaps even exceeding the record for postseason appearances (14), which is held by Paul Assenmacher (1997 Indians) and Brandon Morrow (2017 Dodgers).
Honestly, if a postseason game doesn’t involve Louis Varland at this point, should it even count?
Hershiser’s two complete games in which he allowed a total of two runs on seven hits in the Dodgers’ 1988 World Series triumph over the A’s rightly remains the stuff of L.A. legend. Yamamoto, having already thrown nine complete innings of one-run ball in Game 2, can put a similar stamp on his terrific 2025 and perhaps put himself in position for the World Series MVP honor.
The last pitcher with multiple complete games in a single World Series was Tom Glavine with the 1992 Braves.
The right player at the wrong time for the New York Yankees, Donnie Baseball never reached the World Series in his great playing career (his lone postseason appearance came in his final season of 1995). After more than 40 years in professional baseball, he finally got here as bench coach for the Blue Jays and has compared it to finally getting to eat a hot fudge sundae after always watching others get their taste.
A ring would be an even sweeter treat for one of the most respected people in the sport.
Betts, a member of the 2018 Red Sox and 2020 and 2024 Dodgers, could join them, with plenty of Hall of Fame career left to get one for the thumb.
Immediately after his tremendous, 12-strikeout performance in Game 5, Yesavage was talking about being available for Game 6. We don’t know if the Jays would actually take him up on it in a Game 6 or Game 7, but just imagine Yesavage punctuating maybe the most insane rookie season with a contribution to a World Series clincher. The guy could never throw another pitch in the big leagues, and he’d still be a legend. Perhaps the Series MVP, as well.
Only seven pitchers aged 22 or younger have started two victories in a World Series for a team that won it all:
Hernández and Larry Sherry (1959 Dodgers) are the only rookie pitchers to win World Series MVP.
Not trying to put any additional pressure on the Dodgers’ catcher, but let’s not forget that an incredible streak is at stake as this Series wraps up.
Certainly, if the Dodgers’ Will Smith can extend this streak to an impressive sixth year, he will be the most famous Will Smith in existence.
