Boston Red Sox: Biggest heartbreaks in franchise history

Boston Red Sox pitcher Derek Lowe reacts after walking the winning run to lose the game against the Baltimore Orioles 2-1 05 April 2001 at Camden Yards in Baltimore, MD. AFP PHOTO/HEATHER HALL (Photo by HEATHER HALL / AFP) (Photo credit should read HEATHER HALL/AFP via Getty Images)
Boston Red Sox pitcher Derek Lowe reacts after walking the winning run to lose the game against the Baltimore Orioles 2-1 05 April 2001 at Camden Yards in Baltimore, MD. AFP PHOTO/HEATHER HALL (Photo by HEATHER HALL / AFP) (Photo credit should read HEATHER HALL/AFP via Getty Images) /
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FLUSHING, NY – OCTOBER 27: Jim Rice #14 of the Boston Red Sox kneels at home plate during Game seven of the 1986 World Series against the New York Mets at Shea Stadium on October 27, 1986 in Flushing, New York. The Mets defeated the Red Sox 8-5 to win the World Series 4 games to 3. (Photo by T.G. Higgins/Getty Images)
FLUSHING, NY – OCTOBER 27: Jim Rice #14 of the Boston Red Sox kneels at home plate during Game seven of the 1986 World Series against the New York Mets at Shea Stadium on October 27, 1986 in Flushing, New York. The Mets defeated the Red Sox 8-5 to win the World Series 4 games to 3. (Photo by T.G. Higgins/Getty Images) /

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.