Punching bags in pinstripes: 6 most vilified Yankees players ever

Yankees manager Brian Cashman stops Brett Gardner, who is charging toward the umpire, at Rogers Center on Aug 9, 2019.

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Yankees fans are baseball’s most passionate cheerleaders and that passion often translates into love or hate for players. With the Yankees amassing 27 titles and remaining the best-known sports brand for a century, they seldom accept a player failing the team or going down the bar set by expectations. Here are the six most detested Yankees through the years.

Carl Pavano: A villain in pinstripes


Topping the list is Carl Pavano, whose name still elicits groans from Yankees fans. Before the 2005 season, New York signed the right-hander to a four-year, nearly $40 million contract after he had proven himself as a durable innings eater with the Marlins, even finishing sixth in Cy Young voting in 2004 after posting a 3.00 ERA over 222.1 innings.

Unfortunately, his Yankees tenure was far less successful. In addition to poor performance – a 5.00 ERA over 26 starts from 2005-2008 – he constantly battled injuries, some rather suspicious. Pavano missed all of 2006 with shoulder problems (likely legitimate), bruised buttocks, and broken ribs from a car accident he failed to disclose to the team until they planned to activate him from the IL. He later underwent Tommy John surgery and dealt with other vague “ailments,” suggesting a lack of interest in pitching for New York beyond collecting his paycheck. Good riddance.

Jack McDowell: The man who earned fans’ scorn


Jack McDowell‘s inclusion is amusing since he only played one season with the Yankees after being traded from the White Sox, where he was a perennial Cy Young contender. His numbers in New York weren’t terrible – a 3.93 ERA over 217.2 innings – but definitely underwhelmed relative to expectations when acquired.

However, what truly earned McDowell the fans’ scorn was flipping off the Yankee Stadium crowd after being pulled from a 1995 game. Add serving up the series-losing hit to the Mariners that October, and you have an all-time villain in Yankees lore. Though his performance was mediocre but adequate, his contemptible antics solidified his infamy.

Chris Carter: A new record for infamy


When New York signed Chris Carter before 2017, they hoped to acquire his prodigious power after he’d just led the NL in home runs with Milwaukee. While known for abundant strikeouts and low batting averages, those flaws could potentially be overlooked if he was blasting homers.

Unfortunately, that didn’t transpire, as Carter hit only 8 homers in 62 games before being DFA’d. Yankees fans swiftly turned on him, given his particular ineptness at making contact and fielding. Reaching this level of infamy in less than a season is rare, but Carter managed it. The Yankees should’ve known better, as Carter’s severe strikeout tendencies were well-documented by former teams. They gambled on the power outweighing his flaws, and clearly lost.

Kevin Brown: Yankees fans love to miss


The Yankees acquired Kevin Brown late in his career via trade with the Dodgers, despite existing red flags. While boasting an accomplished track record, injuries were mounting for the righty. Moreover, Brown carried a reputation as a difficult teammate.

In New York, the downsides materialized without the dominance, as Brown managed a 4.95 ERA over 35 starts. His frustration boiled over after one outing, punching a concrete wall and predictably breaking his hand, costing him significant time in 2004. Brown returned for the playoffs but was shelled in Game 7 of the ALCS as Boston completed their storied comeback from a 3-0 deficit. It’s safe to say Brown is not missed by Yankees fans, representing an embittered hire with his production and temperament rapidly deteriorating.

Kei Igawa: Yankees’ biggest international failure


During a Yankees-Red Sox arms race in 2007, New York signed Japanese pitcher Kei Igawa to a 5-year, $20 million contract after paying a $26 million posting fee just to negotiate. This directly responded to Boston acquiring Daisuke Matsuzaka, though Igawa also drew acclaim despite inconsistent MLB success for Japanese players.

Sadly, the investment flopped, as the Yankees spent all that for merely 71.2 innings from Igawa. From 2007-2008, he posted a dreadful 6.66 ERA, earning a reputation for wildness in pressure situations. New York stashed him in the minors until his deal expired, never returning to the bigs after 2008 before going back to Japan. There, injuries plagued his final seasons before retirement. A high-priced international reaction signing went awry.

Joey Gallo: The symbol of hate for Yankees fans


The most recent addition is Joey Gallo, again prompting questions of the Yankees’ rationale. His tremendous left-handed power was alluring for their short porch, evident in his pre-trade homer totals with Texas. However, red flags surrounded Gallo as a recipe for discontent.

The issue has always been contact and strikeouts. After 2021’s trade, he managed just a .160/.303/.404 line despite 13 homers. 2022 was worse – a .621 OPS over 82 games before a merciful exit to the Dodgers. While seemingly a good guy, fans unleashed boos with each unproductive at-bat. For all his power, the precarious hit tool and swing-and-miss tendencies made Gallo an obviously risky acquisition that quickly flamed out.

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2 thoughts on “Punching bags in pinstripes: 6 most vilified Yankees players ever

  1. The only guy deserving of ire on your list should be the one who flipped off the fans. The rest are just some of the large number of investments all across baseball that don’t pan out.

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