MLB: Los Angeles Angels at New York Yankees

Few players can claim as a trophy case as crowded as Derek Jeter. A sparking 20 year career with the same team, five World Series titles, one of the best shortstops in baseball history.

He’s an iconic player and the author of some of the most iconic moments in recent history. Even if the Derek Jeter mythology outgrew the Derek Jeter reality, his role in baseball history is well deserved.

Here are six of the most iconic Derek Jeter moments from his Hall of Fame career, which draws to a close at the end of the 2014 season.

6. The Captain’s 3000th hit leaves the yard

If you’re going to do it, do it with style. Derek Jeter records the 3000th hit of his career by sending a long drive in the seats in left field, becoming just the 28th player to touch this milestone.

If picking up hit number 3000 wasn’t enough, Jeter went 5-5 against Tampa Bay this day, driving in the winning run in the eighth inning. Like I said, iconic.

5. The Dive

This was just another Thursday night game in July at the height of the Red Sox/Yankees rivalry. It wasn’t a big October moment like so many other Derek Jeter highlights.

Which might be why this moment stands out. Jeter gives it his all in a game without playoff implications but because, in the top of the 12th inning, the situation demanded it.

Despite his cool demeanor and well-cultivated image, it is the sight of Derek Jeter dazed and bloody that sticks in the mind of so many baseball fans.

4. The Jump Throw

Although the Jeter jump throw reached a level of self-mockery over the years, there is no doubt it remains the everlasting image Jeter on defense.

Derek Jeter’s defensive reputation is not stellar and, if we’re being honest, become more about his image than his performance. But the incredibly athletic jump and arm strength required to pull this off over and over and over and over throughout the years deserves a little more respect.

3. His entire 2009 Season

New York Yankees player Jeter celebrates as he holds the World Series trophy with teammates in New YorK

For all his career accomplishments, Derek Jeter was never named the most valuable player in the American League. He finished sixth in his best season by WAR (1999) and famously finished second behind Justin Morneau in 2006.

By 2009, Derek Jeter was 35 and just coming off one of the worst seasons of his career. The Yankees spent big to bolster their rotation and lineup, bringing in A.J. Burnett, CC Sabathia, and Mark Teixeira in pursuit of another World Series title – a title the expensive club delivered.

But Derek Jeter was the best player on that team, hitting .334/.406/.465 while playing 153 games. Jeter even worked on his defense in the off-season after some well-placed whispers made their way to his ear.

Jeter’s 6.6 WAR is the second best season by a shortstop age-35 or above in the live ball era. It was exactly what the Yankees needed, hitting .344/.432/.563 in the postseason as the Bronx Bombers claimed their 27th World Series title.

Best shortstop season by WAR, age-35 and older

Rk Player WAR/pos Year Age PA HR SB OPS
1 Luke Appling 7.6 1943 36 677 3 27 .825
2 Derek Jeter 6.6 2009 35 716 18 30 .871
3 Pee Wee Reese 6.0 1954 35 661 10 8 .859
4 Eddie Joost 6.0 1951 35 667 19 10 .870
5 Luke Appling 5.9 1946 39 659 1 6 .762
Provided by View Play Index Tool Used
Generated 2/14/2014.

2. Mr. November

It probably shouldn’t matter that the Yankees went on to lose this series, as Derek Jeter’s Game Four heroics allowed the series to go seven games (only to see Arizona improbably win).

This shot off the embattled Byung-Hung Kim tied the series at two games apiece. And though Jeter struggled slightly against the DBacks powerful pitching in this series, the image of Jeter rounding first base with his hand held high is one of the everlasting images of his baseball career.

It is a moment and an image like this that will live on longer than those who remember that this home run was one of only four hits the Captain had all series. It was a Yankee Stadium opposite field cheapie for the ages.

1. The Flip

This play stands out for two reasons – the first is the magnitude of the moment. The Yankees were behind in the series, facing elimination. Jason Giambi‘s run represented the tying run, as the Yankees clung to a 1-0 edge in the seventh inning.

So the play was huge. But, more than anything, the play was weird. It was so unusual and out of the ordinary. “What was the shortstop doing in foul territory on the first base side???” It didn’t make sense. But Jeter, for whatever reason, made a great read and a great flip and kept the Yankees in front.

Perhaps this moment took on more importance over the years, especially compared to the work Mariano Rivera did in the ninth inning, retiring the dangerous Eric Chavez and Jeremy Giambi with the dying run on second base. But this play is so unique, so memorable and lines up so perfectly with the Derek Jeter mythology, it has to be number one on the list.