The Cleveland Guardians have the longest active World Series drought in MLB, as the franchise has the unfortunate distinction of being ringless since 1949, with four losses in the Fall Classic during that time frame.
Two of those four World Series losses came in the mid-1990s, most notably when they lost in 1997 to the Florida Marlins on a walk-off single in Game 7, which still stings to this day and has many players from that era reminiscing about what could have been if things had gone just a bit differently.
During a recent appearance on The Carlos Baerga Show, legendary pitcher Orel Hershiser stopped by to discuss those Guardians teams and made a bold claim about the kind of success that team was positioned to have if the front office had just spent a little more money.
“If Cleveland would’ve had a bigger budget and Dennis Martinez, and me, and Eddie Murray, and [Dave] Winfield, and all the veterans, if we’d have been in our prime or you would’ve gone out and got different veterans that were more expensive and were in their prime, Cleveland could have won three world championships in a row,” Hershiser said.
If ownership had spent more money in the 1990s, could we have won a World Series? #GuardsBall
"Cleveland could have won three world championships in a row."
– Orel Hershiser pic.twitter.com/dOqk6oWkOY
— Carlos Baerga Show (@BaergaShow) June 11, 2025
Hershiser joining the Guardians from 1995 through 1997 after a decorated career with the Los Angeles Dodgers was a big reason why the team reached the heights that it did.
He had three strong seasons on the mound and went 4-1 with a 1.53 ERA in the 1995 postseason, including an 8-inning gem in Game 5 of the World Series to extend the series before ultimately succumbing to the Atlanta Braves in Game 6.
Unfortunately, his run in the 1997 postseason wasn’t nearly as good, and the 13 earned runs he gave up in ten innings to the Marlins across two starts in the ’97 Series cost the team two games.
Three titles in a row would have been a tall order, but they weren’t too far off from getting to that point.
As for now, let’s just focus on getting one title first and breaking that streak.
NEXT: Report: Guardians Eye Key Moves Before Trade Deadline
