With fewer than 10 days left before the postseason opens on Sept. 29, October’s field is carrying a familiar kind of unfinished business. A collection of established stars — MVPs, Cy Young winners, franchise fixtures and veterans who have seen nearly everything else — are still hunting the one piece of hardware missing from their clubhouse shelves: a World Series ring.
Every club currently holding a playoff place, or sitting within three games of one, has a player who knows how long that wait can feel. Some have been close enough to see the Commissioner’s Trophy on the other side of the dugout. Others have made plenty of October trips without ever reaching the final round.
American League veterans still chasing the last win
Tampa Bay Rays: Yandy Díaz
Díaz is in his 10th Major League season and eighth with Tampa Bay, still serving as one of the most reliable bats in the Rays lineup. The two-time All-Star and 2023 American League batting champion leads the AL in hits, narrowly ahead of teammate Chandler Simpson in the batting-title chase.
The 35-year-old designated hitter has reached the postseason six times, including five trips with Tampa Bay, and appeared in one World Series. Even after enjoying a tomahawk steak when the Rays secured their postseason berth last week, Díaz has made clear that the larger appetite is for his first championship. Freddy Peralta and Drew Rasmussen are also among Tampa Bay players without a ring.
Chicago White Sox: Randal Grichuk
Grichuk has made a career out of adapting to new clubhouses. In 13 seasons, the 35-year-old outfielder and designated hitter has played for eight organizations, compiling a .768 career OPS and 225 home runs.
He has made three postseason appearances but has not won a title. As the surprising White Sox keep pushing through the stretch, Grichuk has a chance to turn a well-traveled career into his first October celebration.
Houston Astros: Christian Walker
Walker enters the closing stretch one home run shy of 200 for his career. His most recent blast was his 25th of 2026, giving him six seasons with at least 25 homers. Over 12 Major League seasons, the Astros first baseman has put together a .770 career OPS and won three Gold Gloves.
His playoff history came during his eight years with Arizona, including postseason trips in 2017 and 2023. The latter ended with the Diamondbacks’ unexpected run to the World Series, but not a ring. Houston hopes Walker, Josh Hader and Isaac Paredes can help supply another deep October run.
New York Yankees: Aaron Judge
Judge’s chase is tied directly to his health. The three-time AL MVP returned from an extended injured-list stay caused by a rib injury, then landed back on the IL 10 days later with a right calf strain. He will miss the rest of the regular season, leaving his availability for October — and how much he could contribute if he returns — uncertain.
In his brief comeback, Judge went 4-for-23, a .174 average, with one homer. Still, the Yankees’ hopes remain heavily tied to the sport’s premier player without a championship. Judge has made eight postseason trips in 11 seasons and appeared in one World Series. Jazz Chisholm Jr., Gerrit Cole, Paul Goldschmidt, Carlos Rodón and Giancarlo Stanton are other Yankees still seeking a first ring.
Boston Red Sox: Sonny Gray
Gray has pitched in October for Oakland in 2013, the Yankees in 2017 and Minnesota in 2023, but the World Series remains untouched territory for the 36-year-old right-hander. He also spent time with Cincinnati and St. Louis before joining Boston this season.
He has been outstanding in 2026, posting a 2.82 ERA across 163 innings in 28 starts while moving beyond 2,000 career innings. Boston is closing in on a second straight playoff berth after a three-year postseason absence. Trevor Story and Ranger Suárez are also on the Red Sox list of veterans without championship jewelry.
Cleveland Guardians: José Ramírez
Ramírez already owns a place among Cleveland’s greatest players. In 14 seasons with the organization, he is a seven-time All-Star and six-time Silver Slugger winner, ranking second in franchise history in homers with 297, RBIs with 1,000 and steals with 321. He is third in runs scored at 1,068 and fifth in hits with 1,773.
He has also landed in the top five of AL MVP voting six times without taking home that award. A title would likely mean more to him anyway. Ramírez has appeared in seven postseasons and one World Series, while Cleveland is pursuing its third consecutive playoff berth under manager Stephen Vogt.
Texas Rangers: Jacob deGrom
DeGrom reached the 2015 World Series with the Mets, though Kansas City hit him hard in a Game 2 defeat and went on to win the Series in five games. He later produced one of the great sustained runs by a modern starter, carrying a 1.94 ERA over 91 starts from 2018 through 2021.
But injuries and thin offensive support limited his October opportunities in New York. His only other Mets postseason appearance came in Game 2 of the 2022 National League Wild Card Series, when he worked six strong innings against San Diego. Injuries followed him to Texas, where he made only nine starts across his first two seasons.
Healthy again, deGrom has closed strongly despite an uncharacteristic overall 2026 campaign. He owns a 1.50 ERA over his last four starts, and a Rangers berth would put a seasoned October arm back into the mix.
Toronto Blue Jays: Vladimir Guerrero Jr.
Guerrero was two outs from a championship last fall before Toronto’s seven-game World Series against the Dodgers ended in heartbreak. The six-time All-Star did everything he could during that postseason, hitting .397/.494/.795 with eight home runs.
His 2026 regular season has not met his usual standard, but Guerrero has four playoff appearances in eight Major League seasons and knows the stage well. After coming that close in 2025, the Blue Jays slugger has another chance to get back there. Shane Bieber and Dylan Cease are among Toronto’s other notable players without a World Series title.
National League names with October business left
Milwaukee Brewers: Christian Yelich
Yelich is six home runs and 18 stolen bases away from joining the 250-homer, 250-steal club as its 26th member. Now in his 14th season, he spent his first five years with Miami and the last nine in Milwaukee.
The 34-year-old is a three-time All-Star, three-time Silver Slugger winner, two-time batting champion and the 2018 NL MVP. He has been to the playoffs five times with the Brewers — in 2018, 2020, 2021, 2023 and 2025 — but has not won the final round. A Milwaukee title would be the first World Series championship in franchise history.
Los Angeles Dodgers: Tarik Skubal
Skubal’s move before the Trade Deadline carried some emotion. He left Detroit, the only Major League organization he had known, after becoming one of baseball’s best starters there. Now the two-time AL Cy Young Award winner is focused on helping the Dodgers pursue a third consecutive World Series title.
The left-hander already has a strong October résumé despite only two playoff appearances. In six postseason starts with the Tigers, Skubal posted a 2.04 ERA, struck out 56 and walked six. A ring remains the one thing he has not collected.
Atlanta Braves: Matt Olson
Olson is in his 11th big league season, with six playoff trips and no World Series championship. The four-time All-Star and three-time Gold Glove winner continues to supply a powerful season for Atlanta.
His first year with the Braves came one season after the club won the 2021 championship. Now he is trying to help Atlanta capture its second title of the decade. Reliever Raisel Iglesias is another prominent Brave looking for his first ring.
Chicago Cubs: Kevin Gausman
Gausman arrived from Toronto before the Trade Deadline and has been uneven in Chicago. The 35-year-old right-hander owns a 5.04 ERA in eight Cubs starts, alternating effective outings with difficult ones.
Still, he brings 14 years of experience and six playoff appearances, including last year’s World Series with the Blue Jays. If his form sharpens in time for October, Gausman could become a key variable for a Cubs club looking to make a long run.
Philadelphia Phillies: Bryce Harper
Harper has delivered signature October moments, most notably his go-ahead two-run homer against San Diego in the 2022 NL Championship Series that pushed Philadelphia into the World Series. The Phillies lost that Fall Classic to Houston, leaving the two-time NL MVP still without a title.
In 15 seasons, Harper has made eight postseason appearances, earned nine All-Star selections, won four Silver Sluggers and taken home 2022 NLCS MVP honors. The championship remains the missing achievement. Aaron Nola, J.T. Realmuto, Cristopher Sánchez and Zack Wheeler are fellow Phillies without rings.
San Diego Padres: Manny Machado
Machado is also in his 15th season and remains one championship short. The 34-year-old third baseman has spent all but one of those seasons with Baltimore or San Diego. His lone stop elsewhere came with the Dodgers in 2018, when Los Angeles reached the World Series but lost to Boston.
Machado has not had his best offensive season, performing around league-average even while approaching his eighth 30-homer campaign. But the Padres have played well down the stretch, and a playoff berth would send Machado to October for the eighth time. Fernando Tatis Jr. is another central San Diego player still looking for a first World Series crown.
That is the October pull for every one of them. The regular season can fill a ledger with awards, records and milestones. A few weeks in the postseason can still decide what the veterans remember most.
