When discussing Joe Torre's dynasty Yankee teams from 1996-2001, the '99 New York Yankees are often overlooked despite being an arguably better group than the '96 and 2000 champions. None of those teams had nearly the amount of pressure that the '99 Yankees carried into the season either. The '98 Yankees were one of baseball's all-time greatest teams, winning 114 games in the regular season and romping to the franchise's 24th World Series title with a record of 11-2 in the playoffs. Entering the '99 campaign, the Yankees had extremely high expectations considering the campaign they just had with almost exactly the same roster. Furthermore, they made a blockbuster deal on the day pitchers and catchers reported for perhaps the best pitcher in baseball, Roger Clemens.

The two-time defending Cy Young Award winner had dominated for two seasons with the Toronto Blue Jays, and the Yankees had to deal their ALCS MVP and best starter from the '98 team to get him, David Wells, in addition to lefty specialist Graeme Lloyd and infielder Homer Bush. He was a longtime rival following his many years with the Boston Red Sox, and some Yankee fans were not exactly pleased that they acquired such an enemy who had a reputation for headhunting. Regardless, he was a big acquisition and had similarly high expectations to the club as a whole to carry the already-potent pitching staff in '99.

The starting lineup was almost identical to the '98 squad that scored 965 runs, aside from the losses of Tim Raines to both the Oakland Athletics and lupus and and Darryl Strawberry to both colon cancer recovery and a four-month substance-abuse suspension. Numerous players on offense experienced drop-offs from their '98 seasons, like Scott Brosius, Jorge Posada, Joe Girardi, Shane Spencer, and to a lesser extent, Paul O'Neill and Tino Martinez. Second baseman Chuck Knoblauch was horrid on defense, but he did prove he was still a fine hitter with a .292/.393/.454, 36 doubles, and 18 homers. Another bright spot came from center fielder Bernie Williams. The Yankees nearly let him go to the Red Sox in favor of malcontent slugger Albert Belle, but Belle's last-minute decision to instead sign with the Baltimore Orioles led to the Yankees re-signing Bernie to a big seven-year $87.5 million deal. It was a lot to live up to, but he played in a career-high 158 games and hit .342/.435/.536 with 202 hits, a 416 wOBA and a 149 wRC+.

The story of the season for the Yankees' offense however, was their future captain, a two-time champion already who was building a Hall of Fame resume. Derek Jeter had the greatest season of his career in '99, establishing career-bests in runs (134), hits (219), homers (24), RBI (102), walks (91), total bases (346), wRC+ (157), wOBA (.428), and fWAR (7.5). All three triple slash statistics were career-highs as well, as he hit .349/.438/.552. The pitching staff was good, though again not as amazing as the previous year. David Cone probably had the best season overall with a 3.44 ERA and 73 ERA-, but he struggled after his perfect game in mid-July. Clemens disappointed with a 4.60 ERA 97 ERA-, Andy Pettitte was so inconsistent that he was almost traded to the Philadelphia Phillies at the July 31st deadline, and Hideki Irabu continued to disappoint fans who expected much more from him upon his '97 stateside debut. The staff was stabilized by Orlando "El Duque" Hernandez, who improved upon his rookie campaign and was eventually the #1 starter come October. Mariano Rivera was reliable again in '99, saving 45 with a 1.83 ERA and 39 ERA-, and the bullpen led by Ramiro Mendoza, Jason Grimsley, Jeff Nelson, and Mike Stanton pitched to a 3.77 ERA. The Yankees would need all of the help they could get, as they faced tighter competition for the American League East division title in '99.

The Red Sox made the playoffs in '98 as the Wild Card and their stars turned in tremendous seasons. The front office felt comfortable enough with the offense to not enter a winning bid for former star first baseman Mo Vaughn, who departed in free agency to the Anaheim Angels, and they still had five players combine for 115 homers--former Yankee Mike Stanley, young catcher Jason Varitek, Rookie of the Year candidate Brian Daubach, outfielder Troy O'Leary, and of course, NOMAH. Shortstop Nomar Garciaparra finished runner-up for AL MVP in '98 with 35 homers, but he had arguably a better season in '99. He won the batting title and hit .357/.418/.603 with a career-high .434 wOBA and 157 wRC+. Then, there was starter Pedro Martinez, who had an all-time great pitching season with 313 strikeouts, a 2.07 ERA (42 ERA-), a minuscule 1.39 FIP (30 FIP-), and an incredible 12.9 fWAR. Though the rest of the pitching staff was suspect, they were a force to be reckoned with and it took a stellar 50-31 record in the second for the Yankees to put them away. Even so, the 98-64 Yankees finished only four games ahead of the Wild-Card winning Red Sox.

The Yankees began the playoffs against the Texas Rangers, whom they also beat in the Division Series on their way to championships in '96 and '98. The Rangers sought vengeance, but they were instead held to just one run in the three-game sweep by El Duque, Pettitte, Clemens, Rivera, and Nelson. The Yankees then faced the rival Red Sox in the ALCS after Boston rallied from down 2-0 in the Division Series to win three in a row against the Cleveland Indians. El Duque pitched eight great innings in the first game, but they needed an extra-inning walk-off blast from Bernie against closer Rod Beck to beat Boston 4-3. A two-run rally in the seventh helped them take Game 2 by a score of 3-2. They were dominated in Game 3 as Martinez shut them out for two hits in seven inning and struck out 12 while the Boston bats bludgeoned Clemens and the 'pen for 13 runs. It would be the Yankees' only loss of the postseason. Ricky Ledee hit a ninth-inning grand slam against Beck in a 9-2 win, and the Yankees closed out the Red Sox with a 6-1 victory in Game 5, led by El Duque's seven innings of one-run ball. El Duque was named the ALCS MVP for his 1.80 ERA in two starts and 15 innings.

In the World Series, the Yankees faced the Atlanta Braves, the team they came back to defeat in the '96 Fall Classic. The starting pitching was still led by the fearsome trio of Glavine, Maddux, and Smoltz, and Kevin Millwood was a fine addition, especially after he threw a one-hitter against the Houston Astros in the NLDS. Maddux got the Game 1 start when Glavine suffered a stomach virus, and he shut the Yankees out through seven innings while the Braves used a solo homer from NL MVP Chipper Jones against El Duque to take a 1-0 lead. The Yankees rallied for four runs in the eighth on Maddux and closer John Rocker to take the first game though, and Cone pitched seven innings of one-hit ball as they battered Millwood to win Game 2, 7-2. The Yankees needed a comeback from down four runs against Glavine in Game 3, and they got one as Knoblauch tied it in the eighth with a two-run homer and backup outfielder Chad Curtis knocked two out of the park in an extra-inning 6-5 victory (the second was a walk-off homer off Mike Remlinger).

The Braves were now on the brink of getting swept with Clemens looking for his first career World Series victory in Game 4 on October 27, 1999. The Yanks gave Clemens the support he needed with a three-run rally off Smoltz "powered" by four singles and a walk. "The Rocket" was in vintage form, shutting Atlanta out on two hits through 7.2 innings before a pair of hits sent him from the game. The Yankees added an insurance run on playoff cult hero Jim Leyritz's solo homer, and Rivera shut the door on the sweep with a perfect ninth inning. The quiet closer was named the World Series MVP for his 4.2 combined shutout innings in three of the four games.

Fittingly, the Yankees won the final World Series of the 20th century, their 25th overall. It was exactly one every four years, and no other franchise was even close (the St. Louis Cardinals were a distant second with nine titles). The "Drive for 25" was complete and the Yankees were champions again.

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