Jeter achieved two career hit milestones in the second half of the 2009 season. On August 16, 2009, against the Seattle Mariners, Jeter doubled down the right-field line for his 2,675th hit as a shortstop, breaking Luis Aparicio's previous major league record.[113] Then, Jeter became the all-time hits leader as a member of the Yankees (2,722), passing Lou Gehrig on September 11, 2009. The hit was a single off Baltimore Orioles pitcher Chris Tillman in the third inning.[114]
In the 2009 postseason, Jeter batted .355, including .407 in the 2009 World Series,[51] as he won his fifth World Series championship. He was named Sportsman of the Year for 2009 by Sports Illustrated,[115] and won the Roberto Clemente Award, Hank Aaron Award,[116] and his fourth Gold Glove Award.[110] Jeter also finished third in the AL MVP voting, behind Minnesota's Joe Mauer and Yankee teammate Mark Teixeira.[117] It was also the fifth championship for Pettitte, Posada, and Rivera, who along with Jeter were referred to as the "Core Four".[118]
In 2010, Jeter, along with Posada and Rivera, became the first trio of teammates in any of the four major league sports in North America (MLB, NFL, NBA, orNHL) to play in at least 16 consecutive seasons on the same team as teammates.
]The Yankee captain batted .270 with a .340 OBP and .370 SLG, all career lows,[121] as he hit more ground balls than usual.[122] Despite this, Jeter was elected to start at shortstop in the All-Star Game.[123] He rebounded to bat .342 in his last 79 at-bats after making adjustments to his swing with the help of Kevin Long, the Yankees hitting coach, who had successfully helped Nick Swisher and Curtis Granderson make adjustments that improved their production. With Long, Jeter changed the way he strode with his left leg.[120][124] Following the season, Jeter won his fifth Gold Glove award.[125] Jeter committed six errors during the season, his lowest total in 15 full seasons.[126]
"He might go down, when it's all over, as the all-time Yankee."
After the 2010 season, Jeter became a free agent for the first time in his career. At age 36, Jeter appeared to be in decline; Joe Sheehan of Baseball Prospectus suggested that Jeter, once a "good, not great" shortstop, had declined to become "below average" defensively,[121] to the extent that he would likely need to change positions; Cashman later acknowledged that Jeter might need to shift to the outfield.[127] Though Jeter stated that he wanted to remain with the Yankees, negotiations became tense. Jeter's agent,Casey Close, stated that he was "baffled" by the Yankees' approach to the negotiations, and Cashman, now the team's general manager, responded publicly that Jeter should test the open market to ascertain his value, which angered Jeter.[128] According to reports, Jeter initially sought a four-year contract worth between $23 million and $25 million per season.[129] He reached an agreement with the Yankees on a three-year contract for $51 million with an option for a fourth year.[128] He spent the offseason working with Long on adjustments to his swing.[130][131]