A Century of Almost: The Long Wait for Baseball's First World Series Walk-Off Grand Slam
From Christy Mathewson to Armando Benítez, five chances at history that fell just short of the seats.
When Freddie Freeman hit the first walk-off grand slam in World Series history this October, I dove into Baseball Savant's database to understand just how rare this achievement was. But after publishing that analysis, which looked at data back to 2008, something didn't feel quite right. Baseball's rich history stretches back much further, and surely there had to be more to this story. So, I did what any obsessed baseball fan would do: I caved and subscribed to Stathead to access play-by-play data going all the way back to 1903.
Freeman's moment was indeed unprecedented in over 690 World Series games. But what I didn't know then – and what reader Robbie Marriage's insightful comment prompted me to investigate – was just how close we'd come to seeing this moment decades before Baseball Savant's records began.
The Complete History of World Series Walk-Off Opportunities
In the entire history of the Fall Classic, there have been only five instances where a team found themselves with the bases loaded in a potential walk-off situation. Each one tells its own story of what could have been.
1912: The Mathewson Moment
Game 8 of the 1912 World Series (yes, Game 8 – there was a tie earlier in the series) provided our first tantalizing opportunity. The Boston Red Sox faced the legendary Christy Mathewson of the New York Giants in a drama-filled tenth inning. After Fred Snodgrass's infamous error in center field (which would become known as "Snodgrass's Muff") and some strategic walks, Larry Gardner stepped to the plate in the bottom of the 10th inning with the bases loaded and one out.
Gardner didn't need a grand slam – a sacrifice fly would do – and that's exactly what he delivered, giving Boston the championship. It's worth noting that facing one of the greatest pitchers in baseball history, with the World Series on the line, Gardner stayed disciplined and got the job done.
1975: The Prelude to Fisk
Before Carlton Fisk's iconic home run in Game 6 of the 1975 World Series, the Red Sox had another chance to end it in the ninth inning. With the bases loaded and nobody out, Fred Lynn – in the midst of his remarkable rookie season (.311/.401/.566) – came to bat against the Reds' Will McEnaney. In a moment that could have been devastating for Boston, Lynn hit into a double play when Denny Doyle was thrown out at home.
Of course, we know how this story ends – Fisk would launch his historic home run three innings later, giving us one of baseball's most memorable moments. But imagine if Lynn had connected just a bit differently in that ninth inning.
2000: The Subway Series Showdown
The first game of the Subway Series between the Yankees and Mets provided another glimpse of what could have been. With the Yankees trailing 3-2 in the ninth inning, they loaded the bases against Mets closer Armando Benítez. Chuck Knoblauch, like Gardner in 1912, delivered a sacrifice fly to tie the game. The Yankees would eventually win in the 12th inning on José Vizcaíno's walk-off single.
2015: Two Chances, One Game
The 2015 World Series Game 1 between the Royals and Mets – which I initially highlighted as the closest call since 2008 – actually featured two bases-loaded opportunities in extra innings. And I have to laugh at myself here: in my excitement to write about Jarrod Dyson's flyout in the 12th, I completely missed Eric Hosmer's game-winning sacrifice fly in the 14th while wrestling with Baseball Savant's search parameters. (Note to self: sometimes paying for the better research tool is worth it!) Two chances in one game to make history, both resulting in fly balls that fell short of forever. Perhaps there's a lesson here about thorough research being as important as enthusiastic writing…
The Strategy Behind the Scarcity
Reader Robbie Marriage raised a fascinating point in response to my original article: the rarity of these situations isn't just about the difficulty of loading the bases. It's often about strategic decisions by managers to avoid exactly these scenarios.
Just as the Diamondbacks once famously walked Barry Bonds with the bases loaded, many managers throughout World Series history have opted to pitch around dangerous hitters before the bases became loaded, preferring to deal with runners on second and third rather than risk the ultimate walk-off moment.
This makes Freeman's achievement even more remarkable. Not only did he deliver baseball's first World Series walk-off grand slam, but he did it in an era where analytics and strategic thinking make these opportunities even rarer than they were in the past.
A Century in the Making
Looking at these historical near-misses, patterns emerge. Most notably, when teams found themselves with bases loaded in a walk-off situation, they typically played for the single run they needed. Gardner's sacrifice fly in 1912, Knoblauch's in 2000, and Hosmer's in 2015 all speak to this pragmatic approach.
The fact that it took 690+ games for someone to hit a walk-off grand slam isn't just about the difficulty of the moment – it's about the complexity of getting to that moment in the first place. Managers have to be willing to load the bases, pitchers have to be forced into throwing strikes, and batters have to be good enough to make them pay for it all.
Freeman's blast wasn't just a historic first – it was the culmination of over a century of near-misses, strategic decisions, and the perfect alignment of circumstances that make baseball such a fascinating sport. Sometimes you have to look back through history to truly appreciate just how special a moment really is.