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A postseason field that started with 12 teams is down to two, and it could be down to one team by the end of Tuesday night. The Milwaukee Brewers can finish a sweep of the Tampa Bay Rays when they meet in Game 4 of the World Series at Tropicana Field in St. Petersburg.
It is too early to begin thinking about a Brewers repeat. After all, they still must win one more game to capture this year’s title.
Yet the offseason could arrive in hours, though it will likely be interrupted on Dec. 2, when the collective bargaining agreement expires and owners are expected to lock out the players. So, all 12 teams who participated in this year’s playoffs are already plotting how to win the World Series in 2027.
Let’s find one free agent who could increase each of those dozen teams’ championship odds next year.
Happ has been a lifelong Cub and has made it clear he wants to stay in Chicago. If the Cubs extend him the qualifying offer, Happ will probably take the $23.15 million salary for 2027. But if Chicago moves on from Happ, the switch-hitter would be a good fit up I-94 with the Brewers thanks to his Gold Glove defense, high on-base percentage and smart base-running.
Kelly was born and raised in the Phoenix area, so he isn’t necessarily looking to leave the Arizona Diamondbacks. However, the Rays drafted Kelly, and they will need a veteran starter to provide innings next season as they seemingly have no shot at re-signing right-hander Freddy Peralta and Nick Martinez is scheduled for free agency as well. He could be the sort of bounce-back candidate that Tampa has excelled with in recent years.
The Guardians need a power hitter, but they likely won't meet the asking price for the few sluggers scheduled to hit the market. Cleveland also ran out of starting pitching while losing to the Rays in the American League Championship Series. Thus, Holmes would be a good addition as a veteran right-hander in the rotation behind Gavin Williams and left-hander Parker Messick, as this Guards defense would hoover up the many ground balls he produces.
The consensus is that the Dodgers want to open a spot in the lineup for top prospect Josue De Paula and will do so by trading left fielder Teoscar Hernandez. However, there have also been rumblings that the Dodgers want to add a veteran hitter in their attempt to win a third World Series title in four years, and that Suzuki has piqued their interest. Could he be the Hernandez replacement in left field, with De Paula lying in wait as injury insurance?
The Yankees haven’t generated much buzz about being a potential suitor for the two-time Cy Young Award winner, especially after leading MLB in ERA during the regular season. However, left-hander Carlois Rodon and righty Gerrit Cole are starting to show their age, and Max Fried is hardly durable himself. Skubal is a better fit than it appears on the surface, and would allow the team to dangle young arms like Will Warren, Ryan Weathers, Elmer Rodriguez and Carlos Lagrange as trade bait.
The Padres have no reason to overthink this; their most logical move is to re-sign the ace of their staff. King will almost certainly opt out of the 2027and 2028 player options in his contract and seek a longer-term deal in free agency. However, the righty wants to stay in San Diego, and the Padres should want to keep him.
The White Sox’ lack of a veteran stabilizer in their starting rotation showed in the postseason, when their historic turnaround season ended in a blown 2-0 lead to the Guardians in an AL Division Series. Assuming they're not willing to pay up for Skubal, stealing Imanaga away from the crosstown Cubs would be the perfect idea.
The Braves won the National League East this year despite having a rotation ravaged by injuries. So, adding pitching depth is a top priority, and a proven innings-eater like Gausman would help. There's reason to think he could rebound after a down 2027; it wasn't that long ago that he was powering the Blue Jays to the World Series.
The Red Sox need at least one more power hitter, ideally a righty. Arozarena fits the bill, and he would love to play on the big stage that Boston and Fenway Park offer. He'd be the perfect complement to Roman Anthony and Wilyer Abreu and a significant upgrade over the likes of Jarren Duran (if he's even in Boston next year) and Masataka Yoshida.
The Cubs badly need a top-of-the-rotation starter, and Peralta fits the bill. Peralta followed a bad four-month stint with the New York Mets by the ALCS MVP award with the Rays. He and Cubs manager Craig Counsell also have a long history, having spent six seasons together with the Brewers from 2008-13.
It is hard to know exactly what path the Astros will take in the offseason until they fill their general manager vacancy. However, if they continue to aim to be contenders after making the postseason for the ninth time in 10 years, they'll need a veteran starting pitcher to supplement Hunter Brown. Gray is coming off an outstanding season and, at 36, won’t be seeking a long-term commitment.
The Phillies have one of the game's top right-handed relievers in Jhoan Duran, but they need more bullpen depth after the unit ran out of gas toward the end of this season. Signing a top-flight lefty like Morejon would give the Phillies a devastating 1-2 punch late in games.
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