Insomnia and the 1999 Yankees


I go to bed tired. Then I wake up at 1 am, then fell back asleep after.  Wake again at 3 am, then asleep. Then again at 3:45 am. 

What goes through my head at these times?

Specific dates, times. Things like: ‘what was I doing twenty years ago from right now?’

Sounds crazy, but it’s true.

To answer that specifically, in June of 1999 I spent two weeks selling books door-to-door in a Pittsburgh suburb.

Then went home to South Dakota and worked at a car wash in Sioux Falls before going back to college for my sophomore year. Lived rent free, I must note, out of the graciousness of my wonderful Aunt Kathy. **Ed’s note: Thanks Aunt Kathy!**

But lying half awake with insomnia on this night, what also came into my head was:  “write about this: write about the summer of 1999.”

I got up, went into the bathroom, and wrote in my notes: “Write about the summer of 1999.” If I don’t write it down, I’ll forget.

So I wrote it down, and here we are.

The summer of 1999: 20 years ago from right now. It’s currently 4:03 AM on my nightstand alarm clock, and I can’t sleep.

What else do I remember about the summer of ’99?

I saw a bunch of movies that summer: Summer of Sam, The Blair Witch Project, American Pie.

Saw Hootie and The Blowfish at Huset’s Speedway and Collective Soul at Washington Pavilion with Steve Blankenship. Collective Soul covered “Crazy Train”, and Oleander opened. Is there anything more 1999 than ‘Oleander’? Freak of the Week dropped by The Marvelous 3, man I still love that song.

But the biggest thing that sticks out to me about 1999? Besides starting year 2 of college and rooming with The Great Brian Dewald in 301 Binnewies Hall at South Dakota State? That certainly is up there.

What sticks out the most is the Yankees won the World Series again.

Last summer I put down 4,000+ words on the 20th Anniversary of the 125-50 Yankees. As it currently stands, the 1999 Yankees are the last team in baseball to repeat as champions. (They actually won a third straight in 2000, but I can save that for next summer and the 20th anniversary of the Subway Series).

It’s interesting to think: How did they repeat?

We now see Boston getting out of the gate slowly this season, after the best season they ever had. It brings to mind how the Yankees did out of the gate in 1999?

I get it, you don’t care. But I’ve covered that already so don’t need an explanation. But in case you do: Don Mattingly: The bricklayer of a baseball dynasty

Here’s a better thought: what happened the year after each current MLB team had their best regular season ever, regardless of if they won the World Series or not?

After all, this is my damn blog so we can look.

The first noted year below is best regular season record in team history, then their record the following year after:

Anaheim Angels, 2008: 100-62; then the next year in 2009: 97-65

Arizona Diamondbacks, 1999: 100-62; 2000: 85-77

Atlanta Braves, 1998: 106-56; 1999: 103-59

Baltimore Orioles, 1969: 109-53; 1970: 108-54* (won World Series)

Boston Red Sox, 1912: 105-47* (won World Series); 1913: 79-71

Chicago Cubs, 1906: 116-36; 1907: 107-45* (won World Series)

Chicago White Sox, 1917: 100-54* (won World Series); 1918: 57-67

Cleveland Indians, 1954: 111-43; 1955: 93-61

Cincinnati Reds, 1975: 108-54* (won World Series); 1976: 102-60**(won World Series)

Colorado Rockies, 2009: 92-70; 2010: 83-79

Detroit Tigers, 1984: 104-58* (won World Series); 1985: 84-77

Florida Marlins, 1997: 92-70* (won World Series); 1998: 54-108. Yikes.

Houston Astros, 1998: 102-60; 1999: 97-65

Kansas City Royals, 1977: 102-60; 1978: 92-70

Los Angeles Dodgers, 2017: 104-58; 2018: 92-71

Milwaukee Brewers, 2011: 96-60; 2012: 83-79

Minnesota Twins, 1965: 102-60; 1966: 89-73

New York Mets, 1986: 108-54* (won World Series); 1987: 92-70

New York Yankees, 1998: 114-48* (won World Series); 1999: 98-64** (won World Series)

Oakland Athletics, 1988: 104-58; 1989: 99-63* (won World Series)

Philadelphia Phillies, 2011: 102-60; 2012: 81-81

Pittsburgh Pirates, 1909: 110-42* (won World Series); 1910: 86-67

San Diego Padres, 1998: 98-64; 1999: 74-78

San Francisco Giants, 1993: 103-59; 1994: 55-60 (strike-shortened season)

Seattle Mariners, 2001: 116-46; 2002: 93-69

St. Louis Cardinals, 1942: 106-48*(won World Series); 1943: 105-49

Tampa Bay Rays, 2008: 97-65; 2009: 84-78

Texas Rangers, 2011: 96-66; 2012: 93-69

Toronto Blue Jays, 1985: 99-62; 1986: 86-76

Washington Nationals, 2012: 98-64; 2013: 86-76

That’s a lot to take in.

A few things stand out:

*Only 9 times has a team gone on to win the title after posting their most regular-season wins in franchise history: 1909 Pirates, 1912 Red Sox, 1917 White Sox, ’42 Cardinals, ’75 Reds, ’84 Tigers, ’86 Mets, ’97 Marlins, and ’98 Yankees.

*Only ’76 Reds, and ’99 Yankees repeated as champs after posting franchise record wins + a title.

*Four teams had their all-time high water win mark in 1998: Braves, Padres, Yankees, and Astros. Which means there were teams that took some serious L’s that year: Marlin’s 108 losses, Rays 99, Montreal Expos 97, Arizona Diamondbacks 97.

*Only one team in the AL Central had winning record in ’98: Cleveland. The White Sox finished in second place with a losing record, 80-82.


So how are the ’99 Yankees the last to repeat? What has happened in the last 20 years?

A bunch of things could factor into this.

One was they returned nearly their entire roster from 1998. Give or take a few guys that didn’t return: David Wells, Homer Bush, Graeme Lloyd, Tim Raines; having the majority of their roster return the following year was a major positive.

Another could be the Wild Card inception in 1995: more teams make the postseason than ever before. Now with the Wild Card and play-in games: could that be why it’s harder to repeat? Could it be more teams, more parity, and more competitive balance then ever?

Before you throw “Payroll/big market vs. small market” at me, just remember this:

Kansas City, Houston, Philadelphia, St. Louis, and Chicago have all won championships in recent years with great player development without being a top-10 payroll team. To further prove that point, let’s look at another list: here’s every championship team in the last 20 seasons, and where they ranked in MLB Payroll that season:

1999: Yankees #1

2000: Yankees #1

2001: Diamondbacks: #8

2002: Anaheim Angels: #15

2003: Florida Marlins #25

2004: Red Sox #2

2005: White Sox #13

2006: St. Louis Cardinals #11

2007: Boston Red Sox #2

2008: Philadelphia Phillies #12

2009: New York Yankees #1

2010: San Francisco Giants #10

2011: St. Louis Cardinals #11

2012: San Francisco Giants #8

2013: Boston Red Sox #4

2014: San Francisco Giants #7

2015: Kansas City Royals #15

2016: Chicago Cubs #14

2017: Houston Astros #18

2018: Boston Red Sox #1

So what does this all mean?

It means big spending doesn’t always mean a championship.

In fact, only 4 times in the last 20 seasons has the team with the biggest payroll won the title (3x the Yankees, 1x Boston).

What I do know is the Yankees followed up their historic ’98 campaign with another championship in 1999.

It was fun to research the storylines from that ’99 season:

  1. David Cone’s Perfect Game on Yoga Berra Day at Yankee Stadium
  2. Jeter .349, 219 hits/Bernie .342
  3. Mariano Rivera didn’t allow a run after July 21.
  4. Roger Clemens traded to Yankees in February 1999
  5. 11-1 Postseason

Back to my previous question about how they started out of the gate. Let’s look at their chronological season record:

May 1st: 15-7

June 1st: 30-20

July 1st 47-29

August 1st: 62-41

September 1st: 81-51.

So how is this team the last to win consecutive titles?

Let’s start with the guys in the clubhouse, Jeter and Rivera first.

Eventually both will be first ballot Hall Of Famers, and by 1999 each were full budded young superstars: Jeter was 25, and Rivera was 29.



Statistically, one could argue that 1999 was the best year he had in his career.

He posted career highs that season in hits (219), batting average (.349), home runs (24), RBI’s (102), and WAR (8.0).

“Within the long list of Jeter’s exceptional stats in 1999, there are two that also stand out: He hit a mind-boggling .371 on 0-2 pitches and hit .455 when facing an opposing pitcher for the third time in a game.” –excerpt from “Derek Jeter’s Forgotten MVP Season,” by Lyndsay Berra. 

Jeter also went into the All Star break hitting .371, an astounding first half.

He was 25: an elastic, flexible, and explosive shortstop with lightening-quick hands. It’s crazy to now think he’d go on to play 15 more seasons after ’99.



The only point that needs to be said about Rivera in 1999: He did not give up a run after July 21.

Let me type that again.

He did not give up a run in 1999 after July 21.

That means after July 21st he entered a game and pitched 28 times to finish the regular season, and 8 postseason appearances did not give up a run in any of those times.

*Maybe that’s how you repeat: when your closer doesn’t give up a run for 36 straight appearances*

It’s not easy to do. He’s a unanimous first ballot Hall Of Fame inductee for a reason.


Coney Perfect:

The difference in parody from one season to the next can be staggering. In my piece last summer, I delved into the David Wells perfect game on May 17th and how that seemed to galvanize the 1998 club.

And unbelievably enough: David Cone did the same thing and threw a perfect game one year later at Yankee Stadium on July 18th, 1999.

The previous perfect game before David Wells in ’98 was by Don Larsen all the way back on October 8, 1956. Yogi Berra was the catcher, and after the last out created the memorable scene by jumping into Larsen’s arms.

By early 1999, the relationship between the Yankees and Berra can be called rocky at best, after Berra was canned by George Steinbrenner less than 20 games into the season in 1985. Berra vowed to cut ties, and didn’t have anything to do with the club for 14 years.

But before the ’99 season started, Berra and the club were able to mend as he worked with Jorge Posada in spring training before the year started.

The Yankees went even further, and named July 18 ‘Yogi Berra Day’ at the stadium and honored him before the game. Don Larsen was also there and took part in the festivities.

So what happened next?

David Cone threw a perfect game that day, with Larsen and Berra in attendance. You couldn’t make this up.




Bern Baby Bern:

Lost in the Core Fore lore is Bernie Williams, who for all practical purposes one could argue was probably the best all-around player in baseball in 1999. He arrived a few years before Jeter, Posada, Pettitte, Rivera and in his early years principal owner George Steinbrenner spent several offseason’s trying to get rid of him.

Good thing that didn’t happen.

From ’97-’01 Williams was at the peak of his prime, earning a spot on the American League All-Star team for 5 straight years. He was consistently impressive in those years batting cleanup, and helped catapult the Yankees to a World Series three-peat from 1998 to 2000. He won 4 straight Gold Gloves from 1997-’00, and a batting title in ’98.

As for 1999:

.342, 202 hits, 100 walks, 25 HR, 115 RBI’s, .971 OPS. Another Gold Glove in center field.

His signature patient, low-crouching, switch-hitting stance was a prelude to many big moments.

Perhaps none bigger than his heroics in game 1 of the ALCS vs. Boston with a walk-off home run vs. Rod Beck that set the tone for an AL Pennant.  At the time he became the first player in baseball history to his two postseason walk-off home runs, his other previous in the ’96 ALCS vs. Baltimore.



Speaking of Wells…

In February 1999 the Yankees traded Boomer to Toronto along with Graeme Lloyd and Homer Bush for Roger Clemens.

Wells was heartbroken, and said at the time: “It’s tough. Give me a couple days.”

Yankees manager Joe Torre said the day of the trade to the media, as quoted in the Washington Post: “There’s some shock in that room right now. It’s something you have to get used to. That is what the game is all about. There are going to be changes. . . . Roger Clemens is a nonstop Hall of Famer.”

Well, that’s not exactly how it’s played out.

In 1999 Clemens didn’t have his best season, going 14-10 and posting a career high ERA of 4.36 in his first season in the Bronx.

But he won the ALDS clincher vs. Texas, throwing 7 shutout innings to clinch the sweep vs. the Rangers.

An emotional Clemens was then shelled by his former team at Boston during game 3 of the ALCS in his Fenway Park return. He started the Yankees only loss of the playoffs, lasting only two innings in a 13-1 rout.

The starting pitcher Clemens was against? He was up against an absolutely-out-of-his-mind Pedro Martinez who beat Clemens and the Yankees in game 2.

In ’99 Pedro had one of the greatest pitching seasons in baseball history: winning the Cy Young by going 23-4 in 29 starts. He threw 213 innings and had 313 strikeouts.


Fortunately, the Yankees only had to face Pedro once that series, and they disposed Boston in 5 games to set up a rematch of the ’96 World Series vs. the Atlanta Braves.

The anticipated rematch didn’t live up to much hype, as the World Series ended in a Yankees sweep. The sweep gave them 8 straight wins vs. Atlanta in the World Series dating back to ’96, and 12 straight World Series wins overall at the time.

As for Clemens? He redeemed himself in a big way in game 4 of the World Series, going 7.2 innings and getting the win in a 4-1 World Series clinching victory.

It would be an understatement to say that Clemens’ baseball legacy not only in New York, but in all of baseball is….complicated.

But of the three Playoff series victories in ’99, he was lights-out and won two of the clinchers and certainly remains a major piece of how the team was able to repeat.

“The Yankees were awesome,” Smoltz said. “I felt in 1996 that we should have won. I can’t say that this time. I feel like the better team won. We had a chance to win every one of these games, but the Yankees had an answer for everything we tried.” -Washington Post, October 28, 1999 following game 4. 


I believe it’s ultimately about players, and those players year after year playing their best baseball. The Yankees from 1996-2001 had more players do that than any team in the last 30 years. The other part is luck: staying healthy, staying together.

I don’t know how the summer and baseball season of 2019 will play out. What I do know is that 20 years ago from right now, the Yankees followed up their greatest season ever in 1998 with another dominant season and a World Series championship.

They were last to win consecutive titles because because David Cone was perfect. They were the last to win consecutive titles because Jeter, Rivera, and Williams were pretty damn close to perfect. They won because Roger Clemens wasn’t perfect in 1999 regular season, but had big playoff moments and righted the ship at just the right time.

Winning the 1999 World Series, their third in four years, defined the club as a dynasty.

20 years ago was a great summer, and that’s something I can rest easy about.

So now the next time I have insomnia, I’ll write about who had the better rock show: Collective Soul or Hootie?