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Once upon a time, the New York Yankees actually cared about competing for World Series titles. It wasn’t about luxury thresholds or sticky stuff. It was about Derek Jeter smacking a hit in the clutch, Mariano Rivera shutting down opposing hitters, and the Core Four (plus Bernie Williams) leading baseball’s last true dynasty.

Life sure has changed in the Bronx.

Despite regularly boasting one of the sport’s highest payrolls, the Yankees will enter the 2022 season without having reached the World Series since 2009. Jeter played his final game in 2014, fittingly notching a single in his final at-bat against the rival Boston Red Sox.

On the eve of the 2022 campaign, now feels like the perfect time to look back at Jeter’s greatest years with the Yankees. For this list, we factored in statistics, the team’s final finish, and the context surrounding the seasons in question.

Based on consideration of the aforementioned prerequisites, Jeter’s greatest campaigns rank as follows:

Honorable mention: Rookie of the Year (1996)

After hitting .250 with seven RBI in 15 games during the 1995 season, Jeter entered the 1996 campaign seemingly headed for Triple-A. However, starting shortstop Tony Fernandez suffered an injury ahead of Opening Day, and new manager Joe Torre turned to Jeter, less than three months shy of turning 22, as his shortstop.

Torre made the right call.

Jeter hit .314 with 10 home runs and 78 RBI as a rookie en route to winning AL Rookie of the Year Award and helping the Yankees reach the playoffs for the first time since 1981. He totaled 3.3 Wins Above Replacement (WAR) and impressed throughout the year with his clutch hitting and his maturity.

Although Jeter only drove in three runs across 15 playoff games, he scored seven — one coming on an infamous home run against the Baltimore Orioles in the American League Championship Series — and threw his arms in jubilation when teammate Charlie Hayes caught the final out of the World Series. A new era of Yankees baseball had arrived, and Jeter was the face of it.

6. One for the thumb (2009)

Referring to the 2009 season as ‘The Last Dance’ would be inaccurate for several reasons, chief among them that Jeter didn’t play his final game until September 2014. However, that 2009 campaign — the first where the Bronx Bombers played in the new Yankee Stadium — marked the last time The Captain won a World Series.

Across 153 regular-season games, the 35-year-old Jeter hit an impressive .334 with 18 home runs, 66 RBIs, and stole 30 bases en route to finishing third in AL MVP voting. The veteran shortstop also won his penultimate Gold Glove and Silver Slugger awards.

Fittingly, Jeter blasted the first postseason home run in the new Yankee Stadium’s history and hit .407 against the Philadelphia Phillies in the World Series. Unfortunately for Yankees fans, the Bronx Bombers haven’t returned to the Fall Classic since.

5. The missing AL MVP Award (2006)

For much of the 2006 season, it appeared the MVP race would come down to Jeter (.343 average, 214 hits, 14 home runs, 97 RBI, 34 stolen bases, and 5.6 WAR) or Boston Red Sox designated hitter David Ortiz (.287 average, an American League-high 54 home runs and 137 RBI, and 5.8 WAR).

Instead, the honor went to Minnesota Twins first baseman Justin Morneau, who hit .321 with 34 home runs, 130 RBI, and totaled 4.3 WAR.

Um, excuse me?

If voters preferred typical counting stats, they should have gone with Ortiz, who terrorized opponents all year. If voters wanted an all-around player, Jeter would have easily been a worthwhile choice, especially considering the Yankees’ 97 wins led all of baseball. Instead, voters chose Morneau for…some reason. We’re still not sure. Jeter had bigger issues after the Yankees lost in the ALDS for the second straight year despite his .500 average in the four-game set.

4. World Series MVP (2000)

Unofficially, the last night of the Yankees’ dynasty ended on Nov. 4, 2001, when Arizona Diamondbacks outfielder Luis Gonzalez blooped a walk-off single to end the Fall Classic. A year earlier, Jeter ensured the dynasty featured four World Series rings, in large part because he hit .339 with 15 home runs, 73 RBI, and 22 stolen bases on a Yankees team that won the AL pennant for the fourth time in five years.

After homering twice in the ALCS, Jeter mashed another two home runs, both solo shots, and scored six runs en route to a five-game series over the crosstown Mets. For his efforts, Jeter earned World Series MVP for the only time in his career.

3. Mr. November (2001)

Honestly, the narratives surrounding Jeter’s 2001 season were nearly enough to make this the No. 1 choice. The 27-year-old did his part in the regular season, hitting .311 with a career-high 21 home runs, 74 RBI, 35 doubles, and 27 stolen bases. He hit .444 in the ALDS to help the Yankees rally from a 2-0 series deficit against the Oakland Athletics.

But, there are two significant moments that stand out above all else. First, there was The Flip.

Then came the early hours of Nov. 1. The Yankees entered the ninth inning trailing 3-1 and risking going down, fittingly, 3-1 in the World Series. Veteran first baseman Tino Martinez, then in the last days of his first stint with the Yankees, crushed a game-tying home run to right-center field in the ninth inning. An inning later, and only minutes after the series made history by having a game played in November, Jeter lined a home run over the short-field porch.

Over thirty-four years after Reggie Jackson became Mr. October, Yankees radio announcer Michael Kay declared Jeter as “Mr. November.” Yankee Stadium shook as the star shortstop rounded the bases and gave the Bronx Bombers new life. Alas, the team lost the series in seven games and wouldn’t win another ring until 2009.

2. The greatest team ever (1998)

Jeter’s 1998 and 1999 seasons are essentially 1A and 1B in terms of his best campaigns. The 24-year-old shortstop earned All-Star honors for the first time in the former year, hitting .324 with 19 home runs, 84 RBI, 30 stolen bases, and a career-high 219 hits en route to placing third in the AL MVP balloting.

Although Jeter struggled in the first two rounds of the postseason, he mashed in the World Series, hitting a robust .353 in 20 at-bats against the San Diego Padres. The 114-win Yankees captured another 11 victories in the postseason and cemented themselves as the greatest team in baseball history.

Were the 1998 Yankees more dominant than the 1995-96 Chicago Bulls, who went 72-10 and (unlike the 73-9 Golden State Warriors) won the NBA Finals? We’ll let you decide. But the answer is probably not.

1. End of the century (1999)

If there were still any baseball fans who doubted Jeter’s greatness and future when the 1999 campaign began, they almost certainly thought otherwise when the season ended. Jeter set career marks in batting average (.349), hits (219), home runs (24), and RBI (102) for the AL East champions.

Luckily for the Yankees, Jeter’s regular-season success translated to the postseason. The 24-year-old hit a combined .375 in the playoffs, including .350 in the World Series, and brought a 25th championship to the Bronx. Although Yankees fans could reasonably pick any of the six seasons as his best, we feel comfortable going with his 1999 numbers.

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