5/26/09: Ten Years Gone - Revisiting the 1999 Boston Red Sox

Sean Sylver
The Fox Hole
Published in
6 min readJun 18, 2015

Before the “curse” was reversed, before the explosion of “Red Sox Nation,” before “Cowboy Up,” the “Idiots,” the bloody sock, and “Manny Being Manny,” before the pink hats, Monster seats and “Extra Innings Extra,” there were the 1999 Boston Red Sox. With Jimy Williams managing the squad and Dan Duquette calling the shots, the ’99 Sox finished 94–68 and clinched the American League Wild Card, coming back from a 2–0 deficit to beat the Cleveland Indians in the Division Series before finally falling to the Yankees in five games in the ALCS.

They didn’t win or even get to the World Series, but the ’99 Sox will forever be one of my favorite Boston squads. As a sixteen year old , I was in-between my 165-pound sophomore year and my 6'4", 190-pound, slightly-less-awkward campaign at Dennis-Yarmouth Regional High School. I didn’t have a girlfriend. I didn’t even have my license. I spent my summer working on the lawns of nearly every little old lady within a two-mile radius of my home. I listened to sports radio all day and to Joe Castiglione and Jerry Trupiano calling the games at night. The next morning, I reviewed the box scores in the Cape Cod Times. I was obsessed. And yet, it was never a particularly good team on paper. Like many Duquette-era models, it was an odd assembly of a couple All-Stars, scrap-heap veterans and hollow prospects — and if we got lucky — a few guys would have career years.

‘99 was the ultimate example of this. Mo Vaughn had left for California. All-Star closer Tom Gordon went down with a serious arm injury. At the height of the “Steroid Era,” no one hit 30 homers. Only one guy cracked .300 and one pitcher hauled in more than 10 wins. That was all that was needed. The folksy Williams led this plucky group of players all the way to the big stage against the Yankees, where, predictably, they wilted. But the ride was pretty fun.

In celebration of the tenth Anniversary of the ’99 Sox, I give you some observations on a unique season in franchise history:

Pedro Martinez goes 23–4 with a 2.07 ERA and 313 strikeouts in only 29 starts (a mid-July injury while pitching against the Marlins shuts him down for three weeks — the seven runs he allows in that one start account for 14% of his season total). It’s the most dominating season by any pitcher in my lifetime, period. Everyone else is, to quote Larry Bird, “playing for second place.” Pedro was a 5'11" monster. Untouchable.

The Sox’ other starters? Journeyman Mark Portugal, the immortal Pat Rapp, and never-was Brian Rose. Poor Bret Saberhagen pitches to a 10–6 record with a 2.95 ERA while his arm was falling off. The Sox appear to one-up the Mariners (and their pursuit of Ichiro) by starting not one but two Asian pitchers, as Korean phenom Jin Ho Cho and Japanese hurler Tomo Ohka combine to take the hill nine times. Even Ramon Martinez (he of 135 career wins but now mostly known as Pedro’s brother) got a couple of turns.

Nomar Garciaparra hits .357, winning the first of two batting titles. Man, he was good. What happened?

The All-Star Game comes to Fenway, complete with a bizarre Home Run Derby where a number of suspected steroid users launch home runs over the Monster (the finals: Mark McGwire vs. Jeromy Burnitz — whatever happened to him? Burnitz, I mean). In the actual game, Pedro strikes out Barry Larkin, Larry Walker, Mark McGwire, Sammy Sosa, and Jeff Bagwell in order. The sight of the great Ted Williams turns freakishly huge men into little boys for a few precious moments.

Jose Offerman, he of the four-year, $24 million contract (and replacement to Mo Vaughn) has his only good season as a member of the Red Sox, hitting .294 with 11 homers and 69 RBI, making the All-Star team and committing only 14 errors at second base.

Knuckleballer Tim Wakefield, a 17-game winner the season before, moves to the bullpen in the wake of Flash Gordon’s injury and saves 15 games in 18 chances. The “knuckleballer as a closer” idea remains the modern intellectual property of Jimy Williams. While Leo Durocher and others deployed Hoyt Wilhelm at the end of games, the nature of the role had changed considerably by ‘99. And we haven’t seen it since.

Juan Pena starts the only two games of his major league career in May, winning both, striking out 15 and compiling a 0.69 ERA. The 22-year old was a promising prospect and had thrown a no-hitter in the minors, but arm injuries prematurely ended his 1999 campaign and eventually forced him to retire.

Pitcher John “Way Back” Wasdin, known mostly for giving up tape measure home runs, starts the season 7–0 (career record: 39–39) and a grass roots campaign begins to get him on the American League All-Star team.

27-year old career minor-leaguer Brian Daubach emerges to crack 21 homers and drive in 73 in 381 at-bats. The lefthanded hitter provides a handful of memorable moments and inspires both the “Daubach is my Daddy” t-shirt and future immortalization on a light pole in Cambridge (see image above).

Bill Simmons’ likely second-favorite bullpen of all time is consummated with the recall of “El Guapo” Rich Garces and the acquisition of struggling Cubs closer, the late Rod “Shooter” Beck. The big guy/mullet combo proves almost as amusing as the “two 300-lb. Latin relievers” approach in 2001 (Garces and Carlos Castillo).

Butch Huskey is the team’s big pickup at the trading deadline. At the press conference, Williams is asked if he had met with the slugger. The response goes something like this: “Did I meet him? No. I hit fungoes to him.” I believe this also might’ve been the year when Jimy asked a reporter “what Little League team do you coach?” but I could be mistaken.

DH Reggie Jefferson, who can’t hit lefties to save his life, goes to the bench after the Huskey trade. Jefferson has it out with Williams, is left off the playoff roster, and never plays in the Majors again.

Irishman Troy O’Leary clubs 28 homers and drives in 103 — see a trend here? That’s another career year, folks. A huge grand slam against the Indians in Game 5 the ALDS doesn’t hurt. I celebrate by taking a jubilant, barefoot lap around my parents’ house, nervous as I did so because I didn’t know what it was like for the Red Sox to win a playoff series and I was wondering if a meteor was going to hit the neighbors’ roof.

As I took that lap, I felt the leaves crunch under my feet and the cool texture of the October grass. It’s a feeling I’ll always remember: exactly where I was when I felt the complete euphoria of being a fan of a team that did something significant. I have a lot of the same feelings from 2004, but I was in college then and the experience was different in the company of friends — not to mention in overall magnitude. This was the first time — one of more innocent fandom, before Carl Everett came to town and headbutted Ron Kulpa, before the weird 2001 collapse, Aaron Boone, before two championships and perhaps most importantly, before all the steroid talk took off. Ten years ago, I wasn’t defined by my occupation, political or religious beliefs, geographic location, who I was dating, or the kind of car I drove. I was just a Red Sox fan. One who celebrated the winning streaks and fell into a funk after an extra-innings loss. The memories of that quirky 1999 team have stayed with me — ten years now. And sometimes, I wish I could go back.

This post was originally published to Fire It Up Radio on Blogger, May 26, 2009.

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Sean Sylver
The Fox Hole

Boston-based sports fan, writer, radio personality, avid gardener.