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Criticism
In the midst of Derek Jeter's farewell tour in 2014, ESPN analyst Keith Olbermann drew headlines during his show on ESPN2 by criticizing the shortstops career. Olbermann began the program by stating "Derek Jeter is not the greatest person in human history. He did not invent baseball. He did not discover electricity.He is not the greatest shortstop who ever lived." Prior to Olbermann, there have been few respected sports analysts that have chosen to comment on the New York Yankees captain's career from a negative perspective. Much of Olbermann's criticism was blaming the New York Yankees success over the last 20 years for covering up the blemishes on Derek Jeter's career. Confused with the special treatment Jeter had received throughout the course of the season, Olbermann reviewed specific statistics to support his argument against Jeter which included:Wins Above Replacement(WAR),career On-Base Plus Slugging(OPS) and Defensive Runs Saved(DRS). After showing below average percentages in each of these categories, Olbermann compared Jeter's current vs. his career in three main offensive statistical categories Batting Average, [[On-Base Percentage and Slugging Percentage. Jeter has been significantly lower in all three categories prompting Olbermann to claim "if Jeter benched himself or hit 8th or 9th, the Yankees might actually be in the wildcard race not just mathematically barely alive", referring to the Yankees positioning in the 2014 MLB American League standings.

Much of Derek Jeter's criticism was created by Keith Olbermann, but also shared with Sports Illustrated contributor Allen St.John and SportsNet New York analyst Chris Carlin. St.John who created an article tited Icon or Overrated The Two Stats That Measure Derek Jeter's Greatness, or Lack Thereof discussed both sides of Derek Jeter's career. He would being by explaining Jeter's Hall of Fam Monitor (HOFM) which is a predictive statistic. Jeter's HOFM sits at 337 points which is 207 points above what a player is required to enter Cooperstown. St.John would then counter his pro-Jeter discussion and further support Olbermann's statistical rant. Similar to Olbermann's criticism on Jeter's Wins Above Replacement (WAR) stating "The bottom line: Jeter's JAWS total is 57.0 which ranks him only 12th among shortstops behind Bill Dahlen and Alan Trammell, who aren't in the Hall of Fame." St.John would continue the disapproval of Jeter's on-field career by attacking his defensive play. He would explain that "Only three times in his 20-year career did Jeter post a positive defensive WAR, which means that for most of the two decades the Yankees would have gotten better defense from a shortstop they found in AAA." St.John and Olbermann caused awareness of Jeters decline in offensive statistics due to the attention gained by his "farewell tour" throughout the 2014 MLB season. Both men concluded their criticism by mentioning the successful history of the Yankees and players from different generations such as Babe Ruth, Mickey Mantle, Reggie Jackson and Joe DiMaggio and comparing their statistics with Jeter's. This was an attempt promote their belief of Jeters mediocrity.

Chris Carlin continued the criticism on SportsNet New York. Contrary to Obbermann and St.John, Carline avoided statistical information to support his criticism. His focus was on Derek Jeter's attitude and behaviour regarding his personal celebration. He began by calling the Yankee captain "a fraud" and then followed that up by saying "you (fans) are all suckers" referring to the fans embracing of Jeter. He then said that he was "shocked he (Jeter) is not hurting from patting himself on the back all year." Carlin would proceed to attack Jeter's farewell Gatorade commercial calling it a "pure fantasy and commercials rarely honestly portray the product or the personality featured in them." continuing to expose what he believed was fraudulent behavior.

Response to criticism
The criticism surrounding Jeter would have little effect on the 14-time all-star as he declined any comments regarding Olbermann. However, on September, 26 2014 the New York Yankees faced the Baltimore Orioles" in Jeter's final game at [[Yankee Stadium. A mere three days removed from Keith Olbermann's controversial comments, Jeter would answer the criticism with a memorable performance. In the 7th inning, Jeter would come through with a base hit single to give the Yankees a 5-2 lead over the American League East champion Orioles. Baltimore would post 3 runs in the top of the ninth to eventually tie the game 5-5. After Jose Pirela led off with a single and Brett Gardner sacrificed, the stage would be set for Derek Jeter. The Yankee shortstop came through in the clutch with a walk off single to win the game for the Yankees. Afterward Jeter would comment on the magical performance by simply saying "To be honest with you, I don't know how I played this game" referring to his emotional state prior to the beginning of the game. Yankees manager Joe Girardi added "I don't think there's a more fitting way to an end" after being asked about Jeter's on-field performance. No negative questions or comments similar to the ones made by Olbermann, St.John and Carlin's were asked to Jeter during the post-game press conference. There have been no further comments to date from Olbermann, St.John and Carline regarding Derek Jeter.

Further responses to the original comments by Olbermann have circled. Forbes magazine contributor David Lariviere had a strong opinion regarding Olbermann's comments stating "ESPN should be ashamed by Keith Olbermann's rant about Derek Jeter." He followed up the original statement by ignoring the negative statistical information provided originally by Olbermann and replaced it with statistics that support Jeter. Lariviere noted that "In 16 postseasons, the captain had 200 hits, including 20 home runs and 61 RBIs, for a .308 batting average. He batted .321 in seven World Series." Several other respected media personalities followed Lariviere such as Tony Kornheiser Show producer Mark Sterne and ESPN employee Colin Cowherd. Both Marc Sterne and Colin Cowherd would expose the positive side of Derek Jeter's career. Sterne would start by describing Jeter as "more than just numbers. Jeter is a guy who plays the game the way it should be played." Cowherd chose to responed to criticism against Jeter by taking the average Yankees fan's standpoint stating "Jeter was not about statistics, but for the the hardworking fan" Cowherd followed with other examples of the average Yankee fan to support his stance.