Ranking 10 MLB Franchises Primed For the Most Wins in Next 5 Years
Which teams will win the most games over the next half decade? It's a fun experiment, but it doesn't exactly have a scientific formula to find the answer for.
In constructing this list, we did our best to balance the present with the future, admittedly putting more stock in where each franchise is at now. Also, while teams like the Cleveland Guardians and Tampa Bay Rays consistently win without spending money, it's harder to bank on that continuing as opposed to franchises that you know will spend aggressively. There's way more of a margin for error with larger-budget teams than with clubs that don't invest in free agency and retaining their star players.
With all that acknowledged, here are the 10 teams we expect to win the most games over the next five seasons.
10. Chicago Cubs
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The Cubs weren't necessarily a slam-dunk pick here, as they edged out teams like the Seattle Mariners, Houston Astros, Texas Rangers, Washington Nationals, St. Louis Cardinals and San Francisco Giants.
They currently have two of the top 15 position players in terms of WAR—Pete Crow-Armstrong and Kyle Tucker, per according to FanGraphs. Crow-Armstrong is 23 and won't become a free agent until after the 2030 season. Kyle Tucker is still only 28 years old, but he's in a contract year. If Tucker's long-term future was settled, the Cubs would be more of a sure thing on this list.
But the Cubs have one of the top 10 farm systems in baseball, according to B/R's Joel Reuter. They also have Shota Imanaga, Dansby Swanson and Seiya Suzuki signed for the foreseeable future, and will get Justin Steele back from Tommy John surgery during the first half of this five-year window.
The mixture of some young looming and major-market wherewithal—especially if Tom Ricketts starts acting like it—was enough for the Cubs to sneak onto this list.
9. Baltimore Orioles
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People are right to be down on the 2025 Orioles, and perhaps even question whether Mike Elias is the right person to steer the ship over the long run.
Elias has made his name off of player evaluations and development. Whether he has the killer instinct to push the team over the top is fair to wonder, but his history of drafting talented position players leads you to believe the O's are generally going to be in the mix while he's in control.
Gunnar Henderson can't become a free agent until after the 2028 season. Adley Rutschman—who feels too good not to get back on track after what's been an alarming calendar year—has two more remaining arbitration years after 2025. Jordan Westburg, Jackson Holliday, Colton Cowser, Samuel Basallo and Coby Mayo are other pieces that figure to make significant impacts for the franchise over the next five years.
Again, it's entirely fair to be upset that after letting Corbin Burnes walk in free agency, Elias didn't pivot to signing Max Fried or trading for Garrett Crochet. But between his time as Orioles general manager and scouting director of the Astros, Elias has proven to be an incredible drafter.
With that, the Orioles are probably always going to have a pipeline of young talent to either join their roster or be traded for veteran players.
8. Philadelphia Phillies
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There is a reality that the current Phillies core of Bryce Harper, Trea Turner, Zack Wheeler and Kyle Schwarber is aging. The Phillies will have to decide this upcoming offseason how to proceed with Schwarber, J.T. Realmuto and Ranger Suárez, all of whom are scheduled to become free agents.
Harper and Turner are signed for the entirety of this period, while Wheeler is under contract through the 2027 season. Eventually, all three will experience decline, though each figures to still be pretty productive even when they are no longer at their peaks. Ditto for Schwarber—who seems to be getting better with age—if he's re-signed.
Lefty Cristopher Sánchez is only 28 and was an All-Star a year ago. He's signed through the 2028 season with affordable club options for 2029 and 2030. Orion Kerkering and Mick Abel are other young players who have made positive impacts for the Phillies in 2025, with the organization's top three prospects—Andrew Painter, Aidan Miller and Justin Crawford—all likely to be at the majors by the end of the 2026 season, if not sooner.
There's no question that time is running out for this current core of Phillies. But it isn't difficult to envision a Harper 2.0 Era in Philly where a mix of young talent and inevitable free-agent signings and trades keeps the Phillies in contention.
7. Detroit Tigers
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The Tigers would be even higher on this countdown if they signed reigning AL Cy Young Award winner Tarik Skubal—who can become a free agent after the 2026 season—to a long-term deal.
But with Kerry Carpenter, Riley Greene, Dillon Dingler, Spencer Torkelson, Casey Mize and Jackson Jobe, the Tigers have a lot of high-end young talent. That list could grow if pieces like Jace Jung, Max Clark and Kevin McGonigle—all of whom are part of what B/R's Joel Reuter ranks as one of the top-five farm systems in baseball—develop into stars at the MLB level.
It wouldn't hurt if CEO Cristopher Illitch opens up the checkbook like his late father, Mike, used to in the coming years. Inking Skubal to a long-term contract would be a great place to start.
The Tigers are at the beginning of what should be an extended World Series window that runs for the entirety of the time this list covers.
6. New York Yankees
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How long can Aaron Judge keep doing this? It's hard to say considering he's 33 and has a lengthy injury history. But he seems en route to his third AL MVP in four years, so it's hard to feel like he isn't going to be one of the best players in baseball for most or all of the next five seasons.
The biggest drawbacks for the Yankees is that B/R's Joel Reuter has their farm system ranked as the worst in baseball, and they no longer are the financial hegemon of the sport like they once were.
Still, the Yankees are one of baseball's deepest-pocketed teams, and do have some talented young pieces in Ben Rice, Austin Wells, Jasson Domínguez and Anthony Volpe. Righty Luis Gil is the reigning AL Rookie of the Year, but has an injury history of his own, with the latest chapter being a right lat strain that's kept him from pitching at all this season.
It will be interesting to see if Brian Cashman—who has been the general manager since 1998—continues to serve in that capacity through this entire five-year stretch. But he's still only 57, so there's no reason he couldn't do it if he wants. And while the Yankees haven't won a World Series since 2009, Cashman has demonstrated an ability to keep them as an October participant just about every year.
5. San Diego Padres
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A fight over who will have ownership of the team moving forward did give us a little pause, but it wasn't enough to overcome the amount of things that the Padres have going for them.
Manny Machado is signed through 2033, and the soon-to-be 33-year-old hasn't shown any signs of slowing down in his seventh season in San Diego.
Jackson Merrill had the unfortunate distinction of debuting the same year as Paul Skenes, but would have won Rookie of the Year in just about any other season with what he did last season. Merrill is only 22, and signed through 2034, with a $21 million club option for 2035 that the Padres will almost certainly pick up.
Meanwhile, for as long as it feels like Fernando Tatis Jr. has been around, he's still only 26. He is far removed from the PED suspension that cost him the entire 2022 season, and he has remained extremely productive. He's also gone from being a below average shortstop to an elite right fielder. He's under contract through the 2034 season.
With their big three and president of baseball operations A.J. Preller's ability to make big trades for impact players, the Padres figure to be threats for some time. If only they weren't the in same division as one of the top teams on this list.
4. Atlanta Braves
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The vibes haven't been great for the Braves in what may be manager Brian Snitker's final season, but president of baseball operations Alex Anthopoulos has set them up for long-term success with some of the team-friendly deals his stars are signed to.
Granted, players like Michael Harris II (signed through 2030 with club options for 2031 and 2032), Ozzie Albies (club options for 2026 and 2027 worth just $7 million each) and Austin Riley (signed through 2032 with club option for 2033) need to get back on track this season. But both are signed to deals that pale in comparison to what they would get on the open market.
The three most team-friendly deals belong to the three most important long-term cogs on the team.
- Ronald Acuña Jr. is due $17 million in 2026, with $17 million club options for both 2027 and 2028.
- Spencer Strider will make $64 million between 2026 and 2028, with the Braves holding a $22 million club option on his deal for 2029.
- Matt Olson will make $22 million ever year from 2026 to 2029, and Atlanta will then have to decide whether to pick up his $20 million club option for the 2030 season.
Over the five years that this list is looking at, the Braves will likely have to replace veterans like Chris Sale and Marcell Ozuna. But Anthopoulos has put the Braves in position to have extended success, particularly if Acuña and Strider stay healthy.
3. Boston Red Sox
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The Red Sox need to repair their relationship with Rafael Devers, who is a Hall of Fame-caliber hitter signed to a team-friendly contract that runs through the 2033 season.
But man, chief baseball officer Craig Breslow is almost sitting on too much talent for his own good.
Entering the season, Roman Anthony, Kristian Campbell and Marcelo Mayer were all consensus top 15 prospects in baseball. Campbell and Mayer have already reached the MLB level. There's not currently a spot for Anthony, because Jarren Duran, Ceddanne Rafaela and Wilyer Abreu make up an outfield where all three are 28 or younger.
Breslow also acquired ace Garrett Crochet in a trade with the Chicago White Sox this past offseason. Crochet is pitching at a Cy Young caliber, and he is signed through at least the 2030 season.
It will be interesting to see whether Alex Cora proves to be the long-term answer at manager or not, but this is an organization with a ton of blue-chip talents.
2. New York Mets
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Steve Cohen has brought a credibility to the Mets that didn't exist when the Wilpon's owned the team. He also appears to have struck gold in his pick of David Stearns to be president of baseball operations, as the Mets have done a tremendous job evaluating starting pitching since he's taken over.
Juan Soto hasn't had a perfect start to his 15-year, $765 million deal, but he's one of the most gifted offensive players the sport has ever seen and the Mets are in line to get the 26-year-old's peak seasons during this five-year stretch we are evaluating for.
Francisco Lindor—last year's NL MVP runner-up—is signed through the 2031 season. Lindor is still only 31, and has a chance to cement his Hall of Fame case during the next half decade.
Will the Mets re-sign Pete Alonso when he inevitably opts out after this season? How will Brandon Nimmo's contract age? Are the Mets ever going to be a team under Stearns that gives out megadeals to pitchers, or will they always be looking to find under-the-radar talent to fill out their rotation?
There are definitely some questions to be answered, and the Mets have a middle-of-the-road farm system. But the one-two punch of Cohen and Stearns, along with the duo of Soto and Lindor give us confidence that the Mets are going to be one of the elite franchises in the sport moving forward.
1. Los Angeles Dodgers
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The Dodgers are the defending World Series champions, and there's reason to believe they could add multiple rings to their collection over the next half-decade.
While the big three of Shohei Ohtani, Mookie Betts and Freddie Freeman are all on the wrong side of 30, the future Hall of Famers aren't showing any signs of slowing down.
The Dodgers also have a grip on the Japanese market that's going to give them a competitive advantage over the 29 other teams. They've already got Ohtani, Yoshinobu Yamamoto and Roki Sasaki under contract, which will help them to recruit from a country where they've become the de-facto MLB team.
If there's an area that the Dodgers need to address, it's their inability to keep their pitching healthy. Fortunately for them, they have the financial resources to overcome injuries to their arms. But you shouldn't always have an entire pitching staff's worth of guys who are out.
But president of baseball operations Andrew Friedman is one of the smartest executives in the game, and he has as many resources to work with to keep the Dodgers at the forefront of the sport as you could ask for.
