Boston Red Sox: Biggest heartbreaks in franchise history

Red Sox history is long and filled with memorable wins. They’ve also had their share of truly heartbreaking losses. Here’s a look at the worst of them.

Any team that’s been around as long as the Boston Red Sox have has their share of tough losses to go along with big wins. For some reason, when the Red Sox lost it was always more epic, more crushing, more devastating, more heartbreaking. Perhaps it was because of how star-crossed and dare I say it, cursed the team seemed to be between the years of 1918 and 2004.

We already looked at their greatest victories, single game, series, or otherwise in a previous article. Now it’s time to do the more difficult thing and look at the worst losses in Red Sox history. Some of these hurt at the time and still sting, while others were absolutely heartbreaking and still bother us to varying degrees even after all the Red Sox have won since 2004.

While it may seem masochistic, it’s still important to look back at these gut-punch losses in order to remember Red Sox history and all of the great players who valiantly tried to bring a World Series championship back to New England. More than that, it helps us have a deeper appreciation of what the Red Sox have done over the last twenty years.

In chronological order, let’s begin.

Red Sox lose 1946 World Series

Despite all of his individual accomplishments as the Greatest Hitter Who Ever Lived, Ted Williams only ever played in one World Series during his career. The Red Sox were one of the best teams in the American League during the 1940s, but only have one pennant to show for it. That came in 1946 when Williams led the Sox to a 104-50 record (the best in franchise history until the 2018 team went 108-54) and the World Series.

This was the first Red Sox pennant since they last won the World Series in 1918 and pitted them against the National League champion St. Louis Cardinals. However, they weren’t at full strength and it was for a reason that would never happen in 2020. Because the Cardinals and Dodgers finished tied atop the National League, they faced off in a best-of-three tiebreaker series to determine the NL pennant.

Since the Red Sox had time to kill before the start of the World Series, they staged an exhibition game where they played against a team of American League All-Stars. During one of his at bats, Ted Williams was hit on his right elbow by a pitch, injuring him and forcing Red Sox manager Joe Cronin to pull him from the game. X-rays showed no damage, but in Williams’ own words his elbow “swelled up like a boiled egg.”

He couldn’t even swing a bat until four days later, on the eve of the World Series, and even then he complained about how sore his elbow was. In any event, the series started on October 6, 1946 and after five games, the Red Sox had taken a 3-2 series lead. With the final two games being played in St. Louis, Boston only needed to win once more to capture their first championship in twenty-eight years.

Instead, what became known as “Slaughter’s Mad Dash,” “Pesky held the ball,” and “Pesky’s hesitation,” depending on your viewpoint, happened in Game Seven. The Cardinals led 3-1 heading into the top of the eighth inning, but Dom DiMaggio hit a two-run double which tied the game and gave the Red Sox life. It was in the bottom of the inning that the infamous incident happened.

With two outs and the Cardinals’ Enos Slaughter on first base, Harry Walker lined a 2-1 pitch to left-center field. Because there were two outs, Slaughter was running on contact. The ball was fielded by Red Sox center fielder Leon Culberson (who had replaced DiMaggio after he had pulled his hamstring). Culberson fired a relay through to Sox shortstop Johnny Pesky who was the cutoff on the play.

Meanwhile, Slaughter ignored the stop sign thrown up by his third base coach and rounded toward home. Pesky turned and, in a play that is still debated to this day, hesitated with his throw. By the time he fired to home plate, Slaughter had slid across with the go-ahead run. Photographs of the play (see the one at the beginning of this slide) show that Pesky’s throw was also weak and well up the third base line.

The “Mad Dash” gave St. Louis a 4-3 lead. In the top of the ninth the Red Sox threatened and had the tying run on third base before being retired to lose the game and the series. As for Williams, due to his injured elbow he only hit a woeful .200 in the series with no home runs and only one RBI. He went hitless in Game Seven, putting up an 0-for-4 showing.

For years he was filled with regret and when asked more than fifty years later what the one thing about his career he would change if given the chance, he pointed to this series. “I’d have done better in the ’46 World Series. God, I would.” In the excellent Williams biography The Kid, he was quoted as saying that he thought he’d get to play in at least one or two more World Series after this one.

Alas, he never did although he certainly had two great chances to do so. Unfortunately, those are the next two entries on this list.

Red Sox lose American League tie-breaker game

Two years after losing the World Series in seven games, Ted Williams and the Red Sox were back in the thick of things in 1948. All season, the American League was a dogfight between the Sox, New York Yankees, and the Cleveland Indians and when the dust settled and the season finished, the Yankees had bowed out while the Red Sox and Indians found themselves tied with identical 96-58 records.

That set the stage for a one-game tiebreaker. In previous years, a tie at the end of the season was handled with a best-of-three series (see the 1946 St. Louis Cardinals). However, because he thought the injury Ted Williams suffered during that layoff was the reason the Red Sox had lost the ’46 World Series, then-manager Joe Cronin had petitioned the league to make the next tiebreaker a single game.

Cronin got his wish and the American League adopted the single-game tiebreaker format (the National League continued to use best-of-three series until switching to the single game format after the 1962 season). The Sox and Indians faced off with fans across New England hoping for a Red Sox win and an all-Boston World Series (the Boston Braves had already won the National League pennant).

Unfortunately, the Red Sox played terribly in the game and Cleveland raced out to a 6-1 lead after five innings. For reasons that are unknown and still debated, Boston manager Joe McCarthy started Denny Galehouse instead of Mel Parnell who had already beaten the Indians three times earlier in the season. Cleveland cruised to an easy 8-3 win to capture their first pennant since 1920; they’d go on to defeat the Braves in the World Series.

Meanwhile, the Red Sox and their fans experienced another bitter disappointment in losing the game. Had Cronin left the best-of-three format as is, the Red Sox would have had two more chances to win the pennant. As Oscar Wilde said: “there are only two tragedies in life: one is not getting what one wants, the other is getting it.”

Fans had been dreaming of an intercity World Series and Williams was trying to get back to the World Series, but neither were to be. It would end up being the Red Sox last appearance in a postseason game until the 1967 World Series.

Red Sox can’t beat the Yankees in the season’s final series

Following the disappointment of the 1948 season, the Red Sox came back in 1949 and fell 12.5 games behind the Yankees by the Fourth of July. However, they went on a tear after that and heading into the final two games of the season at Yankee Stadium the Red Sox had a one game lead in the standings.

All they needed to do was win one of the final two games against the Yankees and the 1949 American League pennant would be theirs. Instead, they somehow lost both games and finished the season 96-58, one game behind the Yankees. Mel Parnell started the first game and the Red Sox had a 4-0 lead but couldn’t hold on as the Yankees won the game 5-4.

That meant that the final game of the season between the two bitter rivals would determine who win the pennant. Ellis Kinder got the start for the Red Sox and gave up a single run to the Yankees in the first inning, but heading into the eighth inning it was still a 1-0 game. Boston manager Joe McCarthy pinch-hit for Kinder but the new hitter failed to do anything.

Now forced to put a new pitcher in for the bottom of the inning, McCarthy inexplicably put Mel Parnell in the game in relief. He gave up a home run and a single before being lifted for another pitcher, Tex Hughson. Hughson told McCarthy his arm was sore, but the manager didn’t care and insisted he pitch. With the bases load, he gave up a soft fly ball to right field that Red Sox outfielder Al Zarilla charged in on.

Instead of making the shoestring catch he attempted, the ball got past Zarilla for a three-run triple. The Red Sox scored three runs in the top of the ninth, but it was too little, too late and they lost the game and the pennant.

For the second year in a row, McCarthy’s managerial decisions were questioned by the sports media and for the second year in a row, the Red Sox squandered a golden opportunity to get back to the World Series.

It would be the last time Ted Williams had a chance to play in and win a World Series and it would be another eighteen years before the Red Sox would win another pennant.

Red Sox Nation is rudely awakened from the Impossible Dream

This one is perhaps not as heartbreaking as some of the others on the list, especially given the expectations Red Sox fans had heading into the 1967 season, but it still deserves to be on here. After going twenty-one years without a pennant, the Red Sox had a fantastic season in 1967 that came down to the wire before they won the American League and made it back to the World Series.

Facing them were the National League champion St. Louis Cardinals, winners of 101 games and the World Series just three years prior. Leading up to 1968 which would become known as The Year of the Pitcher, the ’67 World Series was dominated by pitching. Boston’s Jim Lonborg put up a valiant effort, winning Games Two and Five by throwing two complete games and only giving up one run total.

But it was Hall of Famer Bob Gibson of the Cardinals who completely dominated the Red Sox. He threw three complete games (Games One, Four, and Seven) while only giving up a total of three runs the entire series. This despite the fact that Triple Crown winner Carl Yastrzemski hit .400 in the World Series with 3 home runs, 5 RBI, a whopping .500 OBP and a 1.340 OPS. Lonborg did his best, going 2-1 in the series, but it just wasn’t enough.

The Red Sox were down three games to one after the first four but then won the next two to force a deciding seventh game. In that final game, Gibson and Lonborg finally faced each other, but Lonborg was going on two days rest while Gibson was pitching on three. It wasn’t close as the Cardinals built a 4-1 lead after five innings and ended up winning the game 7-2 to defeat the Red Sox.

The Red Sox seemed like a team of destiny in 1967 and the Impossible Dream almost became a reality, but the Cardinals scuppered that and broke the hearts of Red Sox fans. It would be eight years before they’d return to the World Series.

Red Sox lose 1975 World Series

After losing the 1967 World Series, the Red Sox spent most of the next several years finishing second or third in the American League East (divisions being added to Major League Baseball after the 1968 season). The closest they came to making the postseason was in 1972 when they finished a half game behind the Detroit Tigers.

That was due to the fact that the Red Sox played one fewer game than the Tigers caused by a players strike during the first two weeks of the season. None of the missed games were to be made up resulting in some team’s playing more games than others, hence the Red Sox coming out on the wrong end. In 1975, though, they left no doubt by going 95-65 and finishing 4.5 games ahead of second place Baltimore.

After sweeping the Oakland A’s, winners of the last three World Series in a row, in the ALCS, the Red Sox faced the Cincinnati Reds in the World Series. The Reds had already won two pennants in the 1970s but had yet to win a World Series in the decade. They won 108 games in 1975 and looked to be a formidable opponent standing in Boston’s way.

This World Series ended up being one for the ages and is still often called one of the greatest ever played. It was tied at two games apiece after the first four games and the Red Sox had one of the greatest moments in their history when Carlton Fisk‘s twelfth inning home run won Game Six and forced a deciding seventh game.

In a way only the Red Sox can manage, they lost Game Seven after having a 3-0 lead after five innings. The Reds came back to score two in the sixth, one in the seventh to tie the game, and one in the ninth to take the lead. Carl Yastrzemski, who hit .310 in the series, popped up to make the final out.

Making this one even more excruciating, the Red Sox had at least a one run lead in each of the four games they lost. That’s how close this series was and how close the Sox came to ending their then-57 year drought. It would be eleven years before they’d win another pennant and twenty-nine years before they’d finally win the World Series.

Red Sox lose the 1986 World Series

Here we are at the worst one of all. No matter how you slice it, there was no other World Series the Red Sox had played in where they were as close to winning, so close you could taste it, as in 1986. While they went to a seventh game in 1946, 1967, and 1975, they were never as close as they were in 1986. They were one strike away from winning this one…TWICE…and they still came out on the losing end.

There are so many things about this series that make it painful. The Red Sox won the first two games of the series on the road at Shea Stadium to take a 2-0 lead… and then lost the first two games at Fenway Park.  They won game five at Fenway and headed back to New York City up 3-2 and only needing to win one game…

…and they almost did. Game Six lives on in infamy and will for eternity. There are still so many ways to pick it apart and second-guess it. The Red Sox led 2-0 after two innings but the Mets tied it up with two in the fifth. The Red Sox picked one up in the seventh but the Mets again tied it in the eighth and the score was knotted at three runs apiece after nine innings.

That tying run in the bottom of the eighth, though? Red Sox fans have been debating that for over thirty years now. Then-manager John McNamara has claimed that Roger Clemens complained of having a blister and asked to come out of the game. Clemens has said he never asked to leave the game and that he protested but McNamara wouldn’t listen.

Most fans (and players) seem to side with Clemens, especially since he was pitching well, but in any case it set in motion a chain of disastrous events. McNamara put Red Sox reliever Calvin Schiraldi in for Clemens in the eighth and he gave up the tying run. In the tenth inning, the Red Sox scored two runs but it could have been more had McNamara pinch-hit for Schiraldi (who ended up striking out).

Still, with a two run lead the Red Sox started the bottom of the tenth by retiring the first two batters. The scoreboard at Shea Stadium even flashed a graphic that said “Congratulations Boston Red Sox, 1986 World Series Champions.” Then, disaster. Schiraldi gave up back-to-back singles before being getting to two strikes on Ray Knight.

On an 0-2 pitch, Knight hit a single to drive in a run and brought the tying run to third base. McNamara pulled Schiraldi for Bob Stanley. The next sequence of events was like watching a slow-motion car crash. Stanley threw a pitch in the dirt that got past catcher Rich Gedman and allowed the tying run to score from third.

That also allowed Knight to move into scoring position. Then, Mookie Wilson hit the infamous slow grounder that went between first baseman Bill Buckner‘s legs, allowing Knight to score the winning run. Incredibly, the Red Sox had failed to close it out and the Mets were alive. Even worse, the Red Sox had a 3-0 lead after five innings in Game Seven before coughing it up and losing 8-5.

On a personal level, this one still hurts badly. Since coming back to win the ALCS after being down three games to one, the 1986 Red Sox had seemed like a team of destiny, but instead they came up just a hair short and broke out hearts. This was the first of these defeats that I was able to witness live as it happened and despite all the Red Sox have done since 2004, I still carry the scars from this one. I know I’m not alone.

They had this one. They should’ve won it. I’ll go to my grave believing that.

Red Sox lose the 2003 ALCS

If losing the 1986 World Series was the most heartbreaking loss in Red Sox history, then the 2003 ALCS is a very close second.  The mutual hatred fueling the Red Sox/Yankees rivalry was still burning red-hot in 2003 and it seemed like the Red Sox were finally ready to defeat their hated rivals.

While the Red Sox had made three postseason appearances since 1995 and failed to advance to the World Series, the Yankees had won five pennants and four World Series during that same time frame leading up to the 2003 postseason. The Red Sox had also never in their history beaten the Yankees in postseason play, but it looked like this would finally be the year.

The two teams split the first four games while showing that the rivalry was alive and well. In Game Three, a benches clearing brawl resulted in Pedro Martinez throwing Yankees coach (and former Red Sox manager) Don Zimmer to the ground. Later in the game, two Yankees, Karim Garcia and Jeff Nelson, beat up a groundskeeper in the bullpen in the middle of the ninth inning.

The teams split Games Five and Six which set the stage for an epic finish and it was epic, although not in the way Red Sox fans hoped. It looked good when the Red Sox put up three runs in the second inning and jumped out to a 4-0 lead after four. Even though their bats went quiet afterward, with only a David Ortiz solo home run in the eighth inning tacked on, they went into the bottom of the eighth with a 5-2 lead.

It looked like the Red Sox were finally going to beat the Yankees and in the Bronx, no less. Pedro went out to pitch the eighth inning, having thrown brilliantly to that point. Even though he was approaching the 100 pitch mark, manager Grady Little acquiesced to Pedro’s wishes to keep pitching. Unfortunately, disaster struck and the Yankees started hitting Pedro, eventually putting up three runs to tie the game.

We all know what happened next. The two teams were tied going into the bottom of the eleventh inning and Red Sox pitcher Tim Wakefield started his second inning of relief. On Wakefield’s first pitch of the eleventh, the light-hitting Aaron Boone (he’d hit six home runs all season) hit a solo home run over the left field wall to give the Yankees the pennant. Shades of Bucky Dent, indeed.

It was one of the most crushing losses in Red Sox history and now that I think of it, it’s probably worse than the 1986 World Series. In 1986, the Red Sox still had another game and another chance to win the World Series after blowing their Game Six lead; by contrast, the 2003 Red Sox saw their lead vanish and their pennant hopes go up in flames.

If the cathartic and redemptive comeback in the 2004 ALCS hadn’t happened, this one would hurt even more than it already does.

Red Sox lose 2008 ALCS

I hesitated to put this one on the list because it wasn’t really crushing or heartbreaking like the previous losses. It’s also difficult to consider anything that’s happened post-2004 heartbreaking. The Red Sox had won the 2007 World Series and were the defending champions heading into the postseason in 2008.

Led by American League MVP Dustin Pedroia, the team was trying to win a second consecutive pennant and get back to the World Series. Standing in their way were the pesky Tampa Bay Rays who edged the Red Sox out for the division by two games. After winning the first game, the Red Sox lost the next three and found themselves in a familiar place down 3-1.

Just like the previous year’s ALCS, the Red Sox came storming back and forced a deciding seventh game. They took a 1-0 lead after the first inning but didn’t score any more as Tampa put up three to go up 3-1 heading into the eighth inning. The Red Sox looked like they would break through in the top of the inning by loading the bases, but future Red Sox pitcher David Price got JD Drew to strike out with two outs to end the threat.

The Red Sox would lose the game 3-1 and the series and while this one was by no means heartbreaking, it was definitely one that got away. It’s also the only time this century that the Red Sox followed up a World Series victory with a credible postseason run and a chance to repeat.

Red Sox blow Wild Card in September 2011

Again, it’s hard to justify putting anything post-2004 on this list, but if there’s one moment (or series of moments) that deserves to be on here from the last twenty years, it’s this one. The Sox looked to avenge their third place finish in 2010 by reloading and spending a ton of money in the offseason.

They traded for Adrian Gonzalez and signed free agent Carl Crawford. On paper the team looked absolutely loaded and there were numerous headlines both in New England and the national media calling the 2011 one of the best teams ever, before they’d even played a single game.

The season didn’t go quite that well, but the Sox were still firmly in control of their destiny. The division looked out of reach thanks to the New York Yankees, but the Red Sox seemed to have a stranglehold on the Wild Card. Heading into September, the Sox had a nine game lead in the Wild Card over the Tampa Bay Rays.

As the Rays continued to play great baseball, the Red Sox utterly collapsed, going 7-27 during the month including a horrific blown save in the ninth inning of their final game of the season in Baltimore. The coup de grace was a failed diving catch by Crawford (who had an abysmal season) which allowed the winning run to score for the Orioles.

The fallout from the collapse was just as bad. Manager Terry Francona was let go and smeared by the team on the way out, GM Theo Epstein left to join the Chicago Cubs, and Jon Lester, Josh Beckett, and John Lackey were exposed as having been playing video games, eating fried chicken, and drinking beer in the clubhouse during games.

It was an incredibly ugly end to a tumultuous season and would lead to the Red Sox most recent nadir in 2012 when they hired the insufferable Bobby Valentine to manage the team. The 2012 Red Sox had the franchise’s worst season since 1966 and had so many character issues on the roster that the team underwent a massive housecleaning which led to the glorious 2013 season.