Two clubs in today’s postseason chase are staring at a kind of baggage nobody wants: a World Series drought that keeps stretching. The Cleveland Guardians and Milwaukee Brewers have both put together runs of steady success in recent years, but neither has been able to turn those trips into a championship. Every season that passes only pushes them deeper into an uncomfortable corner of baseball history.
That history gets pretty bleak once you start lining teams up by how long it’s been since their last title. Cleveland sits at the top of the list at 77 years, while Milwaukee and San Diego are tied at 57. Seattle is next at 50, followed by Pittsburgh at 47, Baltimore at 43, Detroit at 42, the Mets at 40, the Athletics at 37 and Cincinnati at 36.
For Cleveland, the number is especially jarring because the drought has been the longest active one in the sport since 2016, when the Cubs beat them in the World Series and snapped Chicago’s 108-year wait. The Guardians have been around since 1901, though the franchise has worn different names over the past 125 years while staying in Cleveland the whole time. They won their first World Series in 1920 and added another in 1948, their most recent championship.
The strange part for Cleveland is that the franchise has actually reached the World Series three times since that 1948 title - and each time, it ran into another team ending a long drought of its own.
Milwaukee’s wait has a different origin story. The city’s modern big league club traces back to 1969, when the Seattle Pilots arrived as one of two expansion teams before relocating to Milwaukee after that lone season.
The Brewers were born in 1970, spent their American League years there until 1998, and then moved into the National League. Milwaukee had already seen other baseball teams come and go, including the Braves, who spent 13 seasons in the city.
The Brewers have reached the World Series only once, in 1982, when they represented the American League and lost to the St. Louis Cardinals.
San Diego’s run without a title is the same length as Milwaukee’s, but the path looks different. The Padres also arrived in 1969 as an expansion team and have never left the city.
Before that, San Diego had hosted plenty of minor league clubs. In 57 seasons, the Padres have made the playoffs 10 times - five as division winners and five as wild-card teams - and their only two World Series trips both ended in losses, to the Detroit Tigers in 1984 and the New York Yankees in 1998.
Seattle’s drought hit 50 years in 2026, and the Mariners occupy a unique spot on the modern MLB map: they are the only active team that has never been to a World Series. The franchise came to life in 1977 after the city lost the Pilots to Milwaukee, and there were stretches when the team’s future in Seattle seemed uncertain. It has stayed put, though, and has reached the postseason six times - four division titles and two wild-card appearances.
Pittsburgh, meanwhile, owns one of the deepest histories in the sport and one of the longest waits for another shot at the top. The Pirates’ five World Series titles are spread across much of the 1900s, but the last came in 1979, when they beat the Orioles.
Since then, the franchise has had only scattered bursts of success: three straight playoff trips from 1990-92, then another three-year run from 2013-15 after a 21-year gap. The Pirates haven’t been back to the postseason since 2015, and they haven’t reached the World Series again since that 1979 title.
In Other News...
Pirates Face A Costly David Bednar Question This Offseason
David Bednars path out of Pittsburgh and into free agency has become one of the more interesting offseason subplots for a club that still needs to sharpen its roster in multiple places. The Pirates moved on from him after a rough start to the 2026 season, only to watch him settle in and finish strong, which makes the trade look a little more complicated now than it did in the moment. The prospects Pittsburgh got back are part of the equation too, but the bigger question is what the Pirates are willing to spend if they want to keep a proven late-inning arm in the mix.
Bednar remains a high-end bullpen option, the kind of reliever any contender would be happy to plug into the back end, but Pittsburgh has to weigh that against a broader list of needs. The bullpen can always use help, yet the front office also has other roster areas demanding attention, and thats where the real tension sits for this winter. The Pirates may like the idea of a reunion, but whether they make a serious push could say more about their offseason priorities than about Bednar himself. [Read more 🡒]
Pirates May Be Running Out Of Time On Their Top Offseason Need
The Pirates have spent the early offseason treating second base as their clearest priority, and Brandon Lowe has emerged as the player most tied to that need. Pittsburgh has been weighing ways to address the spot while the free-agent market still has some depth, but the broader backdrop is making the decision harder. The club would prefer to sort through its options with some patience, especially with other second basemen available if the top target proves too expensive or too difficult to land.
The problem is the calendar may not offer much of that patience. A potential MLB lockout could quickly squeeze the Pirates leverage and limit what they can do if negotiations stall, turning what looked like a measured pursuit into a more urgent one. If the market tightens and Lowe remains available, Pittsburgh may have to decide sooner than planned whether to push hard for him or risk watching its top offseason need linger deeper into the winter. [Read more 🡒]
Pirates Still Lack The Late-Game Edge Contenders Rely On
The Pirates gave themselves something to build on with an 82-80 finish in 2026, their first winning season since 2018, but the run only sharpened the conversation around what still separates a good club from a true contender. In a year when the bullpen showed its flaws, Pittsburgh leaned on arms like Mason Montgomery and Yohan Ramrez, yet the late innings often looked more fragile than teams with October expectations can afford.
For a club trying to turn a modest step forward into a real jump, the relief corps remains the part of the roster that most needs sharpening. The Pirates have enough evidence now to know that better late-game run prevention is not just a luxury, and the next few moves will reveal whether they can turn a promising season into one with staying power. [Read more 🡒]