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Baseball’s Dumbest Gaffes: Gary Sanchez & More

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So much of the media focuses on positives. If you look at Major League Baseball’s official social media accounts, you will see a slew of home runs and great defensive plays.

Well, what about the worst that Major League Baseball has to offer? That is why this article exists.

These are not necessarily the most influential gaffes at each position. These would be best described as the stupidest plays at each position.

With the ground rules out of the way, let us get to a pitcher that struggles to throw a baseball.

Pitcher: Jon Lester (various)

While Jon Lester is a five-time all-star, three-time World Series, and has one of the best postseason pitchers ever. Many fans remember him for his inability to throw to first base. He has cleared up the issue in recent seasons, but it has been immortalized on YouTube where you can find compilations of Lester attempting pick-off throws. Some are good; that’s a start. However, some border on laughable.

Throwing a baseball is difficult, but it is part of a pitcher’s job description. Kudos to Lester for making this gaffe a relic of a past era. Also, kudos to Anthony Rizzo for dealing with Lester.

Catcher: Gary Sanchez (Sept. 10, 2021)

This gaff is what inspired this list.

Major league catchers have made profile mistakes. The 1941 World Series was decided in part due to a catcher mistake. A.J. Pierzynski executed a catcher-on-catcher crime when reaching on a dropped third strike in the 2005 playoffs. These mistakes happen. However, they come fractions of a second after receiving a pitch. The catcher is required to perform a task.

For Gary Sanchez, he would have succeeded had he done nothing. Yes, if Sanchez merely existed, he would not be on this list. However, he decided to turn a tag into an act of stupidity so heinous that Sanchez should be investigated as a gambler.

If Sanchez stands his ground, the baserunner (Jonathan Villar) likely stops in his tracks or leaves the basepath (an automatic out). Villar even began to pull up in preparation to be tagged out.

Instead, Sanchez moved out of the way and permitted Villar to score. Kudos to Joey Gallo for not strangling Sanchez.

First Base: Bill Buckner (Oct. 25, 1986)

Over the last 35 years, Bill Buckner’s E3 has been covered as extensively as perhaps any mistake in any sport. Buckner likely should not have been on the field. Without a wild pitch preceding the “little roller up along first,” Buckner does not allow the game-winning run to score, just the tying run. If Mookie Wilson does not foul off four pitches with two strikes, Buckner would be one of the first to celebrate Boston’s first World Series in 68 years.

Buckner was not substituted out of the game. Bob Stanley threw a wild pitch. Wilson fouled off several pitches before sending a ground ball to Buckner. E3. Ray Knight scores. Game over. The Mets won the World Series two nights (and three Knight hits) later.

Second Base: Luis Castillo (June 12, 2009)

Francisco Rodriguez fires a pitch to Alex Rodriguez. The batter Rodriguez pops the pitch up to second base. He slams his bat down in frustration. The pitcher Rodriguez pumps his fists in the air. He has his 17th save. A three-time Gold Glover named Luis Castillo slides under the ball. Cue Michael Kay.

“Dropped the ball! He dropped the ball! Here comes Teixeira, and the Yankees win! Oh my goodness, he dropped the ball!”

Had there been fewer than two outs, the ball was likely shallow enough for the infield fly rule invoked. However, there were two outs. Both Derek Jeter and Mark Teixeira were in motion. Castillo bobbled the ball. The ball fell to the ground. Castillo fell to the ground. E4.

Third Base: Will Middlebrooks (Oct. 26, 2013)

Sorry Red Sox fans, this is the most unique occurrence of the nine.

With one out in the bottom of the ninth, Jon Jay hit a soft bouncer to Dustin Pedroia. Pedroia fired to catcher Jarrod Saltalamacchia. Out. Saltalamacchia fired to third baseman Will Middlebrooks. The ball gets by Middlebrooks (this is technically the error on Middlebrooks) and rolls into left field.

It is at this point that if Middlebrooks does nothing, Daniel Nava throws out Allen Craig, and the game heads to extras tied at four.

Instead, Middlebrooks does a cross between a push-up and a twerking motion while on the ground, obstructing Craig. Craig is awarded home, and the Cardinals get their second win of the 2013 World Series.

On the bright side (for Red Sox fans), Boston won this World Series, their third in 10 years.

Shortstop: Alex Gonzalez (Oct. 14, 2003)

The Chicago Cubs lead 3-1 in the eighth inning of Game 6 of the 2003 NLCS. However, ace Mark Prior is dealing with runners on the corners and one out. Up steps rookie Miguel Cabrera. Cabrera hits a high bouncer to the Alex Gonzalez that is not his teammate. (Yes, both shortstops that played in this game are named Alex Gonzalez). It is a tailor-made double play.

Gonzalez instead fails to catch the bouncer with the backhand. Cabrera is safe at first. Luis Castillo (yes, the same one from earlier in this article) is safe at third. Ivan Rodriguez is safe at second.

Prior threw one more pitch, which Derrek Lee lined into left for a double, scoring two runs. Walk. Sacrifice fly. Walk. Three-run double. RBI single. Florida scored eight runs in the inning, won the game, won Game 7, and won the World Series.

Left Field: Ryan Raburn (April 26, 2011)

Miguel Olivo launched a ball to the Comerica Park warning track. Ever the humanitarian, left fielder Ryan Raburn provided a few feet of extra distance to the ball courtesy of a collision with his glove. Instead of a fairly routinely long fly-out, Olivo had homered. He circled the bases, scoring Seattle’s first run in an early-season win.

The official scorer did not rule the interaction as an error. To Raburn’s credit, nearly making the play required a Herculean athletic effort.

Kudos to Phil Coke for embracing Raburn rather than choking Raburn when the pair returned to the dugout.

Center Field: Nyjer Morgan (May 22, 2010)

Adam Jones uncorked a fly ball to the wall. Nyjer Morgan retreated to the wall, timing his jump perfectly. The ball bounced off Morgan’s glove, falling to the warning track, right next to Morgan’s hat.

It is at this moment in history that Morgan loses his mind. He is incensed. He launches his glove into the outfield grass. He had just allowed a home run to the other center fielder.

Granted, Morgan did allow a home run, but it was of the inside-the-park variety. Jones motored around the bases, scoring the third run of a three-run home run.

Perhaps the most ironic fact about Morgan is that he finished 2010 with zero home runs. He was statistically more likely to allow an inside-the-park home run than he was to hit a home run of any kind.

Right Field: Larry Walker (April 24, 1994)

It is the bottom of the third at Dodger Stadium. There is one out in the inning. Mike Piazza lofts a long fly ball to future Hall of Famer Larry Walker. Walker drifts into foul ground, making the easy out. Two are gone in the inning. He hands the ball to a lucky kid in the crowd.

Walker takes a step. He takes another step. One more. After his fourth step away from the wall, Walker spins around and asks the kid for the ball back. The two-time reigning Gold Glover forgot how many outs there were. Walker won five more Gold Gloves after the general populace forgot about this.

Thankfully for Walker, counting is an optional skill for baseball Hall of Famers.


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Ryan Potts is an avid football and baseball fan. He covers the NFL and Major League Baseball, focusing on the Baltimore Ravens and Atlanta Braves.