A native of Cincinnati, Ohio, Youkilis played college baseball for his hometown Cincinnati Bearcats (of which Sandy Koufax was a fellow alumnus). While at Cincinnati, he set school records in several offensive categories and earned second team All-America honors during his junior and senior seasons. He was selected in the eighth round of the 2001 amateur draft by the Boston Red Sox and went on to become an integral piece of a Red Sox run. He breezed through the minor leagues, consistently posting freakishly high on-base percentages by drawing large numbers of walks and rarely striking out. He made his major league debut on May 15, 2004, and homered in his second at-bat. He didn’t begin to see regular major league playing time, however, until the 2006 season, when he was converted from a third baseman to a first baseman. By 2007, he was a team leader with both his bat and his glove. At one point during a 23-game hitting streak, he recorded at least two hits in nine straight games, tying a Red Sox record held by Jim Rice. In the field, he led the league with a perfect 1.000 fielding percentage and an American League record 1,079 errorless chances at first base, netting himself a Gold Glove. His streak was finally snapped on June 7, 2008, against the Seattle Mariners, at which point he had logged 238 consecutive errorless games, consisting of 2,002 fielding chances. He won World Series rings in 2004 and 2007. In the 2007 American League Divisional Series against the Cleveland Indians, he enjoyed a spectacular series, batting .500 with 14 hits and three homers. Youkilis gained additional fame when Michael Lewis’ bestselling book “Moneyball” revealed that Oakland A’s general manager Billy Beane referred to him as “Euclis, Greek God of Walks,” because of his skillful ability to foul off pitches and draw bases on balls, thereby increasing his on-base percentage. He was bar mitzvahed at a conservative shul and was known to suit up, but not play, in observance of Yom Kippur. On August 8, 2005, Youkilis took to the outfield in the ninth inning along with teammates Adam Stern and Gabe Kapler, marking the first all-Jewish outfield in major league history. According to fellow Jew Ian Kinsler, Youkilis would always inquire about what Ian was doing for the Jewish holidays whenever their paths crossed during a game.
Youkilis was a three time All-Star (2008, 2009, and 2011).