Legacies can be made or broken in the MLB postseason. They can also be stamped and solidified. So FanSided spoke with a number of executives and scouts about the names that need a storybook ending this October. Some might surprise you; others won't. But all have a legacy riding on a postseason to write home about. Here’s who our sources picked, and what a deep playoff run could mean for each.
Bryce Harper, Philadelphia Phillies
Harper is at the top of this list as a future Hall of Famer who is somehow still missing a ring. Harper and the Phillies got close in 2022, when they fell to the Houston Astros in the World Series. He had his big postseason moment that year, a go-ahead home run in the NLCS to help Philly clinch the pennant. But he now needs the happy ending to his story, and that can only be a title. And let's not forget that the Washington Nationals won a World Series championship the year after he bolted for Philly.
"Bryce Harper needs a title to complete his resume," one rival National League scout told FanSided. "Not sure anyone else has more pressure in regards to their legacy. They have had stacked teams in Philly and the everyday fans know that the Nationals won (a title) after he left."
Manny Machado, San Diego Padres
Like Harper, Machado has been in the league since 2012 and is likely headed for the Hall of Fame. But to really solidify his legacy, Machado, 34, needs to win a ring before he retires. The Padres are one of the hottest teams in baseball right now and have a dominant bullpen. After a down season statistically, Machado needs to get his bat going in the postseason, and carrying the Padres to their first World Series title in franchise history is the ending he needs to stamp his legacy in the game. If Machado has a big October with a storybook ending, his poor regular season will be forgotten. It would also increase his chances at cruising into Cooperstown.
Ronald Acuña Jr., Atlanta Braves
Coming in third is Acuña Jr., who actually has a ring already. But Acuña tore his ACL in 2021, so he did not appear in the postseason for the Braves when they won their World Series title. Atlanta has not made it past the NLDS since, and because he was hurt in '21, scouts and executives believe Acuña Jr. needs to have a big postseason and lead the Braves on a deep run this October. Acuña Jr. being at the forefront of another title run would be just what he needs to enhance his legacy as one of the team's all-time greats.
Zack Wheeler, Philadelphia Phillies
Although he has semi-walked back his previous statement, Wheeler has said in the past that he could retire after his contract expires after the 2027 season. For that, scouts and executives put him at No. 4 on the storybook ending list. Coming off thoracic outlet surgery, Wheeler, at age 36, has posted a 13-5 record and 3.06 ERA in 27 starts for the Phillies this season. Wheeler was also on that Phillies team that came up short in 2022 and then lost in the NLCS the following year to the Arizona Diamondbacks in 2023. He was a member of the Mets in 2015 on their run to the World Series, too, but missed the entire year after undergoing Tommy John surgery. Both Wheeler and Harper could use a title this year, especially with Wheeler's career possibly coming to a close soon.
Gerrit Cole, New York Yankees
For "obvious reasons," as one scout put it, Gerrit Cole could really use a storybook ending with the Yankees this year. Cole, 36, has two more years left on the nine-year, $324 million deal he signed with the Yankees seven years ago. Cole lost in the World Series with the Astros in 2019 and again in 2024 with the Yankees. The future Hall of Famer needs a ring, but he might not get there in a year where Aaron Judge might not be available in the playoffs due to a calf injury. However, if Cole dominates in October and leads the Yankees on a deep run, no one will be questioning his value. The Yankees have to win a championship in the next few years or else they will have wasted their window to do so with both Cole and Judge. The clock is ticking, and that's why this year has to be it. Cole has established himself as a great postseason pitcher; now he needs a title to show for it.
Kevin Cash, Tampa Bay Rays
We have our first manager on the list: Rays skipper Kevin Cash. As one rival AL executive asked: "Can he get over the hump?" Cash's Rays lost to the Dodgers in the 2020 World Series and haven't been back since. Cash's handling of the Rays' pitching staff in that series was also heavily questioned. Tampa is the AL East champion and has a first-round bye, plus home-field advantage in the ALDS and ALCS. After missing out on the postseason the last two years, Cash could use a storybook ending this year to prove the doubters wrong. He needs to prove he can win the big one and show he's the one to lead the Rays to their first World Series title in franchise history.
Pat Murphy, Milwaukee Brewers
Speaking of managers getting over the hump, scouts and executives believe Murphy needs a storybook ending in the playoffs after his team got swept by the Dodgers in the NLCS last year. The back-to-back NL Manager of the Year winner needs to have his team ready and prepared to perform in the postseason this time around, unlike in their last two years. The Brewers are a perennial postseason team, but they haven't won a pennant since 1982. Milwaukee had their franchise's first 100-win season in 2026, but now it's time to show up in October. The Brewers have lofty expectations, and Murphy needs to at least lead the club past the Dodgers in the NL — or else he could start to draw heavy scrutiny for his team not living up to the hype again.
Edwin Diaz, Los Angeles Dodgers
Coming in at No. 8 is closer Edwin Diaz, who has had a nightmare first season with the Dodgers. The good news is that the righty has looked sharp since coming off the IL recently, and could potentially reclaim the closer job in the postseason. If Diaz performs in the playoffs and the Dodgers wind up with a three-peat, all will be forgiven and forgotten. Diaz came into the year already tabbed as one of the best closers in all of baseball. However, he has only been to the postseason twice, with both appearances coming as a member of the Mets. Diaz has a 2.38 ERA for his playoff career; dominating in the postseason this year and closing out another Dodgers World Series title would remind the baseball world how elite he truly is.
Kyle Schwarber, Philadelphia Phillies
Schwarber has a World Series title on his resume with the Chicago Cubs in 2016. But it has been quite some time since he won a ring, and one rival National League executive believes it's time for him to win another. Schwarber could help his teammates Harper and Wheeler get there with his bat. Schwarber has 23 career postseason homers (tied for third all-time). Clubbing seven more this October would make him MLB's all-time postseason home run leader and solidify his legacy as one of the best designated hitters of all-time.
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