1999 Yankees Diary: The 25th anniversary of an overshadowed champion

Everything about the 1998 Yankees’ season was incredible. They are among the most celebrated teams in baseball history for a good reason, and on top of rostering such an impressive group of All-Stars, it really felt like one of those years when everything that could go right did go right. If the 1996 team that launched the dynasty represented a hard-fought catharsis for spending the entire Donnie Baseball Era in championship wilderness, then ‘98 was a 125-win magic carpet ride to the finish line.

This generation of Yankees learned the hard way in ‘97 that repeating was no walk in the park. They narrowly lost the AL East crown to Baltimore, and though they took the Wild Card, Cleveland rallied to crush their dreams in the Division Series. Things like this just happen. For over two decades now, MLB teams have been trying and failing to repeat.

So it would have been a daunting task for the 1999 Yankees to repeat regardless. Again though, they weren’t following any normal champion; they were following those unbelievable ‘98 Yankees. Expectations were sky-high, especially after they acquired the two-time defending AL Cy Young Award winner Roger Clemens on the first day of spring training. In the eyes of most Yankees fans, there were no excuses to miss out on another title.

The path to October glory was not nearly as clear this time around, though. Some aspects of the team remained elite. Derek Jeter continued his breakout with perhaps his career year. Bernie Williams was worth every penny that the Yankees spent to re-sign him. Orlando “El Duque” Hernandez went from cool ‘98 story to Game 1 playoff starter. David Cone had a brush with perfection. Mariano Rivera was as untouchable as ever.

Elsewhere, it wasn’t quite business as usual. Clemens was only OK instead of dominant. Cone got lit up for the rest of the season after his perfect game. Chuck Knoblauch’s fielding yips became nearly untenable. Scott Brosius, Paul O’Neill, and Jorge Posada had major dips in production, and Darryl Strawberry missed nearly the entire season while serving a suspension. Brosius, O’Neill, and Luis Sojo all sadly lost their fathers during the season. The toughest blow of all might have come when beloved manager Joe Torre was diagnosed with prostate cancer in mid-March and had to step away from the team for awhile to address this life-threatening illness.

It would have understandable for such emotional turmoil to derail a season. We’re only human. But these Yankees found a way to not only survive, but thrive. They won an AL-best 98 games and romped through the postseason with an even better record than the ‘98 squad at 11-1, sweeping a damn good Atlanta Braves team in the Fall Classic. The vaunted ‘96 rematch was rendered a laugher.

Twenty-five years later, this remarkable ballclub is somewhat inexplicably forgotten. People obviously remember the late-’90s Yankees dynasty, but they think of the ‘96 and ‘98 far more than ‘99. And while the 2000 Yanks were worse by almost every measure, they were the ones to polish off the three-peat with a much-ballyhooed defeat of the Mets in the Subway Series.

To borrow a cliché, the ‘99 Yankees are the red-headed stepchild of Torre’s dynasty. Even today, there are seemingly no particular plans to celebrate the 25th anniversary of these champions. It could simply be because they reunited just a year ago for the ‘98 celebration and these guys — who had heavy overlap with the ‘99 club — don’t necessarily feel obligated to come back in annual three-year bunches.

Nonetheless, we want to give this terrific team its due. Just as we did for 1998, we will chronicle the daily exploits of the 1999 World Series champions throughout 2024. So many of their stories have been overlooked in the years since, and we aim to bring them to light.

Remember the Drive for 25!

Joe Torre’s battle with cancer
April 5, 1999: L, 3-5 @ Oakland — Clemens debuts, but Yanks lose Opening Day (0-1)
April 6, 1999: W, 7-4 @ Oakland — Bombers grab their first win (1-1)
April 7, 1999: W, 4-0 @ Oakland — Mendoza’s gem paces opening series victory (2-1)
April 8, 1999: off
April 9, 1999: W, 12-2 vs. Detroit — Chili, Yogi warm up rainy home opener (3-1)
April 10, 1999: W, 5-0 vs. Detroit — Home debut a winner for the Rocket (4-1)
April 11, 1999: W, 11-2 vs. Detroit — El Duque flirts with history (5-1)
April 12, 1999: off
April 13, 1999: W, 6-3 vs. Baltimore — Jeter stays hot, Bombers come back late (6-1)
April 14, 1999: W, 14-7 vs. Baltimore — 1,000 ribbies for Paulie (7-1)
April 15, 1999: L, 7-9 vs. Baltimore — Mo, Rocket slip against O’s (7-2)
April 16, 1999: L, 1-8 @ Detroit — Duque drubbed in Detroit (7-3)
April 17, 1999: L, 1-3 @ Detroit — Pettitte’s brilliance overshadowed (7-4)
April 18, 1999: L, 1-5 @ Detroit — Knoblauch’s yips creep in sweep (7-5)
April 19, 1999: off
April 20, 1999: W, 4-0 vs. Texas — Paulie, Coney get Yanks back on track (8-5)
April 21, 1999: W, 4-2 vs. Texas — Jeter’s homer powers Clemens to W (9-5)
April 22, 1999: off
April 23, 1999: W, 6-4 vs. Toronto — Old pals spoil Boomer’s Bronx return (10-5)
April 24, 1999: W, 7-4 vs. Toronto — Young Doc no match for Yanks (11-5)
April 25, 1999: W, 4-3 vs. Toronto — Bernie walks off DiMaggio Day (12-5)
April 26, 1999: off
April 27, 1999: W, 7-6 @ Texas — Ninth-inning comeback off Wetteland (13-5)
April 28, 1999: L, 6-8 @ Texas — Tempers rise in Texas (13-6)
April 29, 1999: W, 5-3 @ Texas — Zim ponders retirement, wins keep coming (14-6)
April 30, 1999: L, 6-13 @ Kansas City — Andy takes one on the chin (14-7)

May 1, 1999: W, 8-4 @ Kansas City — Coney comfy in familiar grounds (15-7)
May 2, 1999: W, 9-8 @ Kansas City — Bernie’s bomb secures slugfest W (16-7)
May 3, 1999: L, 3-9 @ Kansas City — El Duque touched up for seven (16-8)
May 4, 1999: L, 5-8 @ Minnesota — Twins smoke 17 hits off Yankees pitching (16-9)
May 5, 1999: W, 5-3 @ Minnesota — Pettitte-led victory in the Twin Cities (17-9)
May 6, 1999: W, 4-3 @ Minnesota — Injury mars Metrodome win (18-9)
May 7, 1999: W, 10-1 vs. Seattle — Irabu, Jeter sink M’s (19-9)
May 8, 1999: L, 5-14 vs. Seattle — Another tough day for El Duque (19-10)
May 9, 1999: W, 6-1 vs. Seattle — Stanton leads semi-impromptu Bullpen Game (20-10)
May 10, 1999: off
May 11, 1999: L, 7-9 vs. Anaheim — Halos offense too much to handle (20-11)
May 12, 1999: L, 0-1 vs. Anaheim — Finley outduels Cone in gem (20-12)
May 13, 1999: L, 0-2 vs. Anaheim — Swept by the Angels (20-13)
May 14, 1999: L, 2-8 vs. Chicago (AL) — Scuffles continue against ChiSox (20-14)
May 15, 1999: L, 4-12 vs. Chicago (AL) — Five losses in a row (20-15)
May 16, 1999: W, 2-1 vs. Chicago (AL) — Crisis averted! (21-15)
May 17, 1999: off
May 18, 1999: L, 3-6 @ Boston — Torre returns but bullpen stumbles (21-16)
May 19, 1999: L, 0-6 @ Boston — Mid-May struggles linger in Beantown (21-17)
May 20, 1999: W, 3-1 @ Boston — El Duque salvages Fenway series (22-17)
May 21, 1999: off
May 22, 1999: W, 10-2 and L, 1-2 @ Chicago (AL) — Twin bill split (23-18)
May 23, 1999: W, 8-7 @ Chicago (AL) — Ninth-inning comeback avoids series loss (24-18)
May 24, 1999: off
May 25, 1999: L, 2-5 vs. Boston — A step back at home (24-19)
May 26, 1999: W, 8-3 vs. Boston — Bam-Tino’s slam sinks BoSox (25-19)
May 27, 1999: W, 4-1 vs. Boston — Rocket helps two-hit the Red Sox (26-19)
May 28, 1999: W, 10-6 @ Toronto — Jeter paces win at SkyDome (27-19)
May 29, 1999: W, 8-3 @ Toronto — Coney cruises in Canada (28-19)
May 30, 1999: W, 8-3 @ Toronto — More Jeter, more 8-3 finals (29-19)
May 31, 1999: L, 1-7 vs. Cleveland — Streak snapped as so-so May ends (29-20)

June 1, 1999: W, 11-5 vs. Cleveland — Paulie helps Yanks strike back (30-20)
June 2, 1999: L, 7-10 vs. Cleveland — A tough day for Andy Pettitte (30-21)
June 3, 1999: off
June 4, 1999: W, 4-3 vs. New York (NL) — First Subway Series win of ‘99 (31-21)
June 5, 1999: W, 6-3 vs. New York (NL) — Duque throws glove in memorable play (32-21)
June 6, 1999: L, 2-7 vs. New York (NL) — Mets rip Clemens, avoid sweep (32-22)
June 7, 1999: L, 5-6 @ Philadelphia — Ninth-inning rally falls just short (32-23)
June 8, 1999: L, 5-11 @ Philadelphia — Nine-run nightmare in the seventh (32-24)
June 9, 1999: W, 11-5 @ Philadelphia — Back in first place (33-24)
June 10, 1999: off
June 11, 1999: W, 8-4 @ Florida — Late surge wins it for Bombers (34-24)