While researching dubious defensive records, I got to thinking about who had committed the most errors on a single play. This wasn't readily available on the standard leaderboards at Baseball-almanac or Baseball-reference, so I had to do some digging. Eventually, my efforts paid off.
That record belongs to Mike Grady, a catcher and utility infielder who played for the Phillies, Giants and Cardinals between 1894 and 1906. Grady was adept with a bat in his hands--a lieftime .294 hitter who exceeded the .300 mark at the plate in 5 of his 11 big league seasons. His experience as a fielder was an entirely different story. While stationed at the hot corner for the Giants in 1899 following an ejection to the team's regular third baseman, Grady was charged with 4 miscues on one sequence. After botching a grounder (error #1), he threw wildly to first (error #2). As New York's right fielder relayed the ball back to Grady, he dropped it (error #3). At this point, the batter was rounding third. Grady scrambled for the ball and fired wildly over the catcher's head allowing the run to score (error #4).
This may or may not be the most horrific defensive sequence of all-time. Many stories still circulate regarding a hard-hitting outfielder by the name of Smead Jolley who played for the White Sox and Red Sox from 1930 through 1933. Jolley was an excellent run-producer at the plate, reaching the century mark in ribbies twice during his brief career while posting batting averages above .300 in 3 of 4 campaigns. But his fielding misadventures became legendary and he was referred to by one writer as "the greatest stationary outfielder in history." According to numerous (and likely apocryphal) accounts, Jolley once matched Mike Grady's feat of four errors on the same play, though a sympathetic official scorer deliberately failed to credit him with it. As the story goes, a ball rolled through his legs in the outfield (error #1) then bounced off the outfield wall and back through his legs (error #2). Retrieving it, the ham fisted fly-chaser then bobbled the ball (error #3). When he finally gained possession, he fired wildly into the seats, allowing the runner to score (error #4). It's a funny story, but there's no statistical evidence to support it. Various accounts describe different settings for the play (making it a highly debatable occurence). Solid evidence of Jolley's poor fielding exists in his error totals and lifetime fielding percentage, which is more than 20 points below the league average.
(Yet another shameless plug, you can read more about Jolley in my book Cellar Dwellers)
You have to give Jolley credit for trying. According to many sources, the most inept fielder of all-time was first baseman Zeke Bonura, though statistics won't back this up. Why? You can't be charged for an error if you can't get your hands on the ball. The lumbering Bonura was another able-bodied slugger who played 7 seasons for four clubs from 1934 to 1940. In that span, he amassed 351 extra-base hits and hit .307. He also led the league in fielding percentage three times. But according to contemporaries, Bonura made little effort to field anything hit in his direction. Any ball hit outside of his immediate reach was given a disdainful look and a half-hearted wave of the glove, a gesture dubbed by one writer as "The Mussolini Salute." In his own defense, Bonura once told a reporter: "I'm not a lousy fielder. That's one of those stories spread by (manager) Jimmy Dykes and (teammate) Lew Fonseca. They've been labeling me as a poor first baseman for years, by Dykes so I couldn't ask for much money and by Fonseca so he wouldn't lose his job." There may be some truth to that statement, though descriptions of his "laughable" defense are legion.