22 years ago, the New York Yankees selected a skinny, 18-year-old high school shortstop from Michigan with the sixth overall pick of the 1992 Major League Baseball Draft. This player ended up making 13 All-Star teams, leading the franchise to five World Series championship and becoming New York City’s most marketable modern athlete. As we know, that pick was Derek Jeter.

Jeter was passed over by five teams before the Yankees drafted him. Most notably, the Houston Astros were strongly advised by scout Hal Newhouser to select Jeter with the first overall pick. The team’s management ultimately feared that Jeter would end up taking an athletic scholarship to play baseball at the University of Michigan and made the safe choice in taking Phil Nevin from Cal State Fullerton. Nevin only played in 18 Major League games for the Astros before being traded to the Detroit Tigers for an aging relief pitcher. Newhouser ended up quitting his scouting job with the Astros and leaving baseball for good.

Looking back over two decades later, it is clear that Newhouser was justified in his opinion. Derek Jeter’s professional career has spanned 18 years and saw three different U.S. presidents, two Yankee stadiums and the death of owner George Steinbrenner. The consistency and success that he has brought to the Yankees have made him a household name and a New York City icon.

Jeter is now 39 years old and coming off an injury-plagued season in which he only appeared in 17 games. This past Wednesday, he posted an open letter on his Facebook page explaining his decision to retire immediately following this upcoming season.

This will mark the inevitable end of an era for not only New Yorkers, but also for followers of Major League Baseball everywhere. Jeter’s career is marked with great success and signature moments; just two years ago, he led the entire league in hits. This does, however, feel like the right decision for Jeter.

The Yankees are currently in the midst of a major roster overhaul. After C.C. Sabathia’s sharp decline, Alex Rodriguez’s steroid drama, Mariano Rivera’s retirement and Robinson Cano’s signing with the Seattle Mariners, this is a natural opportunity for Jeter to announce his retirement. Additionally, last season was such a huge disappointment for both him and the team that if Jeter is able to sustain any healthy play it will be considered to be a successful final season.

Ideally, Jeter’s season mirrors Mariano Rivera’s 2013 season. Rivera was able to maintain dominance throughout the year, and the second half of the season served as his personal farewell tour. Both players have garnered tremendous respect from around the league, and it would be a shame if anything were to distract from this final season for No. 2.

Derek Jeter has never demanded the spotlight or even topped 25 home runs in a single season, but his legacy will be defined by his many clutch playoff performances and signature moments. Jeter hit the very first pitch of Game Four of the 2000 World Series over the left field wall for a home run. More recently, he became the 28th player to ever reach 3,000 career base hits. He did so in style with another home run in 2011.

In addition to Jeter’s many big moments, his career is filled with accolades and formal recognition. Jeter has amassed five world championships, made 13 All-Star teams, won World Series Most Valuable Player and was named American League Rookie of the Year. Additionally, Jeter has maintained a pristine reputation off the field. While playing through the height of baseball’s steroid era, Jeter was never linked to any major scandals and was a model of professionalism throughout his career.

This coming spring will mark the beginning of Derek Jeter’s final season in Major League Baseball, but his legacy will certainly endure. Jeter will likely be a first-ballot Hall of Famer when first eligible in 2020. He is set to join the likes of Babe Ruth, Joe DiMaggio, Lou Gehrig and Mickey Mantle in Yankee Stadium’s Monument Park.