The Captain: The Journey of Derek Jeter

The Captain: The Journey of Derek Jeter

by Ian O'Connor


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“Derek Jeter is undoubtedly the most talked about, argued about, cheered, booed and ultimately respected baseball player of his generation. And as public a figure as he has been, he is in many ways the least known. That changes now as Ian O’Connor, one of the best sports writers anywhere, goes deep and does what no one has quite been able to do: Tell us a bit about who Derek Jeter really is.”??—??Joe Posnanski, author of The Machine

"Deftly told.”??—??The Washington Post
In The Captain, Ian O’Connor draws on unique access to Derek Jeter and more than 200 new interviews to reveal how a biracial kid from Michigan became New York’s most beloved sports figure and the face of the steroid-free athlete.
O’Connor takes us behind the scenes of a legendary baseball life, from Jeter’s early struggles in the minor leagues, when homesickness and errors threatened a stillborn career, to the heady days of Yankee superiority and nightlife, to the battles with former best friend A-Rod.
All along the way, Jeter has made his Hall-of-Fame destiny look easy. But behind that leadership and hero’s grace there are hidden struggles and complexities that have never been explored, until now.

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Product Details

ISBN-13: 9780547747606
Publisher: HMH Books
Publication date: 04/03/2012
Pages: 448
Sales rank: 155,483
Product dimensions: 5.30(w) x 7.90(h) x 1.10(d)

About the Author

IAN O'CONNOR is a nationally recognized sports columnist who has won numerous Associated Press awards. Currently he writes for and hosts a radio show for ESPN. He is the author of Arnie and Jack, a New York Times bestseller, and The Jump.

Read an Excerpt


Like all good stories about a prince, this one starts in a castle.
 Derek Sanderson Jeter spent his boyhood summers around the
Tiedemann castle of Greenwood Lake, a home near the New York/
New Jersey border maintained by the Tiedemann family of Jersey City
and defined by its medieval-looking tower and rooftop battlements.
 In the 1950s, the Tiedemanns started rebuilding the burned-out
castle with the help of their adopted son, William “Sonny” Connors,
who did his talking with a hammer the same way Charles “Sonny” Liston
did his talking with his fists.
 More than a quarter century later, Connors, a maintenance worker
at a Catholic church, would preach the virtues of an honest day’s work
to his grandson, who was enlisted as Connors’s unpaid assistant when
he wasn’t playing with the Tiedemann grandchildren around the lake.
 Derek Jeter was forever carrying his baseball glove, forever looking
for a game. His grandfather was not an enthusiastic sports fan, but as
much as anyone Connors showed the boy the necessity of running out
every single one of life’s ground balls.
 Connors was a shy and earnest handyman who had lost his parents
to illness when he was young, and who had honed his workshop skills
under John Tiedemann’s careful watch. Tiedemann and his wife, Julia,
raised Sonny along with twelve children of their own, sparing him a
teenager’s life as a ward of the state.
 Tiedemann was a worthy role model for Sonny. He had left school in
the sixth grade to work in a Jersey City foundry and help his widowed
mother pay the bills. At thirteen, Tiedemann already was operating a
small electrical business of his own.
 In the wake of the Great Depression he landed a job inside St. Michael’s
Church, where Tiedemann did everything for Monsignor LeRoy
McWilliams, even built him a parish gym. When Msgr. McWilliams
did not have the money to cover the scaffolding needed to paint St. Michael’s,
Tiedemann invented a jeep-mounted boom that could elevate
a man to the highest reaches of the ceiling. He ultimately got into the
business of painting and decorating church walls.
 Around the same time, in the mid-fifties, Tiedemann was overseeing
work on a 2.7-acre Greenwood Lake, New York, lot he had purchased
for $15,000. His main objective was the restoration of a German-style
castle that had been gutted by fire more than a decade earlier.
Tiedemann’s labor force amounted to his eleven sons, including
his ace plumber, roofer, carpenter, and electrician from St. Michael’s
— Sonny Connors.
 “Sonny was a Tiedemann,” said one of the patriarch’s own, George.
“We all counted him as one of our brothers.”
 And every weekend, year after year after year, this band of Jersey
City brothers gathered to breathe new life into the dark slate-tiled castle,
an Old World hideaway originally built by a New York City dentist
in 1903. The Tiedemann boys started by digging out the ashes and
removing the trees that had grown inside the structure.
 They did this for their father, the self-made man the old St. Michael’s
pastor liked to call “the Michelangelo of the tool chest.” The castle was
John Tiedemann’s dream house, and the boys helped him build additional
homes on the property so some of his thirteen children and
fifty-four grandchildren could live there.
 “We weren’t a huggy, kissy type of family,” George said. “We weren’t
the Waltons. But the love was there, and it didn’t have to manifest itself
more than it did.”
 John Tiedemann was a tough and simple man who liked to fish,
watch boxing, and move the earth with his callused hands. Long before
he poured himself into the Greenwood Lake project, Tiedemann was
proud of being the first resident on his Jersey City block, 7th Street, to
own a television set. He enjoyed having his friends over to take in the
Friday night fights.
 He finally made some real money with his church improvement
business and later bought himself a couple of Rolls-Royces to park outside
his renovated castle. But Tiedemann was a laborer at heart, and he
had taught his eleven sons all the necessary trades.
 As it turned out, none of the boys could match the father as a craftsman.
None but Sonny, the one Tiedemann who did not share Tiedemann’s
 For years Sonny was John’s most reliable aide, at least when he
was not working his full-time job as head of maintenance at Queen
of Peace in North Arlington, New Jersey, an hour’s commute from the
castle. Sonny would drive through heavy snowstorms in the middle of
the night to clean the Queen of Peace parking lots by 4:00 a.m. He
would vacuum the rugs around the altar, paint the priests’ living quarters,
and repair the parishioners’ sputtering cars for no charge.
 Sonny never once called in sick and never once forgot the family
that gave him a chance. Every Friday, payday, Sonny would stop at a
bakery and buy a large strawberry shortcake so all the Tiedemanns
could enjoy dessert.
 “Sonny was the spark that kept us going,” George said, “because he
never took a break.” Sonny idolized Julia Tiedemann, and he liked to
make her husband proud. If John Tiedemann wanted a room painted,
Sonny made sure that room got painted while John was away on business
so he would be pleasantly surprised on his return.
Sonny married a Tiedemann; of course he did. Dorothy was a niece
of John and Julia’s, a devoted Yankees fan who loved hearing the crack
of Joe D.’s bat on the radio, and who hated seeing Babe Ruth’s lifeless
body when she passed his open casket inside Yankee Stadium in 1948.
 Sonny and Dorothy, or Dot, would raise fourteen children, including
another Dorothy, or Dot. The Connors family spent some time in
the castle before moving to nearby West Milford, New Jersey, where
Sonny served as the same working-class hero for his kids that John
Tiedemann was for him.
 Sonny and his wife took in troubled or orphaned children and made
them their own, and it never mattered that money was tight. “Sonny
went back to his own experience as a boy,” said Monsignor Thomas
Madden, the pastor at Queen of Peace. “The Tiedemanns took care of
Sonny, so it was in his nature to take care of others. . . . And Dorothy
had just as big a heart as he did.”
 One of their flesh-and-blood daughters, Dot, ended up in the army
and was stationed in Frankfurt, Germany, where in 1972 she met a
black soldier named Sanderson Charles Jeter, raised by a single mother
in Montgomery, Alabama. They married the following year, at a time
in America when the notion of a biracial president was more absurd
than that of a human colony on Mars.
 Naturally, Sonny did not approve of the marriage. He worried over
the way the children would be treated, worried they would be teased
and taunted by black and white. “Sonny was very concerned about
that,” Msgr. Madden said. “He would ask, ‘Will they be accepted? Will
they have to fight battles?’ ”
 His questions would start to be answered on June 26, 1974, when
Derek Sanderson Jeter was born at Chilton Memorial Hospital in the
Pompton Plains section of Pequannock, New Jersey.
 If Sonny initially did not have a relationship with his daughter’s husband,
that did not stop him from pursuing one with his daughter’s son.
 Derek was four when his parents moved with him from Jersey to
Kalamazoo, Michigan, where Charles enrolled in Western Michigan
University to pursue a master’s and doctorate in social work. But every
summer, Derek stayed with the Connors clan in West Milford and
made almost daily visits to the castle in Greenwood Lake.
 The Tiedemanns put down sand near the water to give the boys and
girls the feel of a beachfront, and Derek’s grandmother brought him
over to play with the Tiedemann grandchildren and escape the heat.
Derek was not looking for a chance to swim as much as he was looking
for a partner in a game of catch.
 “He was always talking about baseball,” said Michael Tiedemann,
one of John’s grandchildren. They played Wiffle ball games and threw
footballs and tennis balls around the lake. “And no matter what we
played,” Michael said, “Derek was by leaps and bounds the best athlete.
He kept his eye on the ball and moved a lot faster than the rest of us
 Despite the fact he was reed thin, Derek surely claimed some of
his physicality from Sonny, a roundish but powerfully built man who
stood five foot eleven and projected the body language of a dockworker
— in other words, someone to be avoided in a bar fight. But it
was Derek’s father, Charles, who passed down the genetic coding of a
 Charles Jeter was a shortstop in the late sixties when he arrived at
Fisk University, a small, historically black school in Nashville. He was
a shortstop until the coach, James Smith, told him he was a second
 Smith had a pro prospect with a throwing arm to die for, name of
Victor Lesley. Lesley was the reason the tall and rangy Jeter was moved
to a less taxing infield spot.
 Jeter was hardly thrilled with the demotion and yet never mentioned
it to his coach. Though he did not have a male figure in his
household while growing up — Jeter never met his father — he knew
how to conduct himself as a perfect gentleman, a credit to the mother
and housecleaner named Lugenia who raised him.
 “Cordial, nice, carried himself the right way,” Smith said. “I never
heard Jeter use a curse word. Ever.”
 On a strong team composed of African Americans from the South
and a small circle of Caribbean recruits from St. Thomas, Jeter was an
excellent fielder and base runner, a decent hitter who liked to punch
the ball to right field, and a selfless teammate who knew how to advance
a runner from one base to the next.
 Jeter was as reliable a sacrifice bunter as Smith had ever seen. “You
could ask him to bunt with three strikes on him if the rules had allowed
it,” Smith said.
 The head coach was the son of one of Nashville’s first black police
officers. Smith was only a few years older than his players, but he was
a strict disciplinarian all the same, a man unafraid of leaving behind a
couple of important players if they were late for the bus.
 The Fisk team, he said, “used to be the laughingstock of the league,”
the Southern Intercollegiate Athletic Conference. He recruited better
talent from American high schools, stumbled upon a pipeline to the
U.S. Virgin Islands, and made sure his players were dressed in shirts
and ties on road trips.
 “They needed to know that when you go to Fisk,” Smith said, “you
represent something besides yourself.”
 Though Fisk had its share of white professors and white exchange
students, Jeter and his teammates forever understood they were members
of a predominantly black institution surrounded by a culture
often hostile to African-American aims. So Smith took no chances. His
student athletes were expected to be ambassadors of the school, the
sport, and the cause of racial equity.
 Charles Jeter fit the serious-minded mold. Only once did Smith
have to reprimand him, and that was after Jeter was thrown out trying
to steal second. Smith had never given him the steal sign, and when
a teammate committed the same mortal baserunning sin the next inning,
Smith went ballistic. “Gentlemen,” he shouted at his players, “this
is a team sport. Let’s not put individual statistics ahead of the team.”
 Jeter was known for his hustle, for his willingness to run out ground
balls, so he was the perfect apostle of this all-for-one, one-for-all approach.
(Smith only heard of his dismay over being moved to second
base through a relative years later.) Jeter did not play to inflate his
numbers on the bases or at the plate. He burned to be part of a winner,
so the demoted shortstop focused on being the best second baseman in
the league.
 Smith shifted the incumbent to right field to clear room for Jeter,
whose quickness and hand speed made him a natural at turning the
double play. Jeter had a glove as flat as a pancake, “and we teased him
about it all the time,” said Ulric Smalls, one of his teammates from St.
Thomas. “When Jeter put it on the ground it had no shape, but he was
flawless in the field.”
 Jeter got his chance to return to shortstop after Lesley left Fisk, and
Smalls remembered him outplaying a Vanderbilt star who had all the
big league scouts abuzz. Smith had left his coaching position before
Jeter finished his collegiate career, but he had scheduled the likes of
Vanderbilt so the scouts fussing over the white boys in the SEC would
be forced to watch his players, too.
 Buck O’Neil, the Negro League star working for the Cubs, was the
only scout who made regular trips to Fisk, leaving Jeter without the
stage he needed to display his command of the game’s fundamentals.
 Smith believed Charles had all the tools and talent to make it to
the big leagues. “If he was playing at a different time and a different
school,” the coach said, “he might’ve made it. But Jeter just didn’t have
the opportunity.”
 Charles Jeter made sure his son had the opportunity by providing
the strong and nurturing paternal presence he had missed as a child,
and by embracing the same code of honor, decency, and hard work that
had shaped the Tiedemann and Connors homes.
 Starting when Derek was in kindergarten, Charles competed against
him in checkers and in card games and challenged him to guess the
value of an appliance on the television show The Price Is Right. Charles
tried to beat Derek at everything, and he told his wife their son “needs
to learn how to lose and how to play the game the right way.”
 Charles coached Derek when the boy was a Kalamazoo Little
Leaguer, when Derek loved nothing more than throwing on his uniform,
standing proudly before a mirror, and marching in the openingday
parade with his chin high and his shoulders thrown back, so proud
to be part of a team.
 Only one day Derek decided he was too proud to finish on the wrong
end of a Little League score. He refused to join the handshake line to
congratulate the winning team, and Charles got in his son’s face and
made a tough-love stand.
 “It’s time to grab a tennis racket,” he barked at Derek, “since you
obviously don’t know how to play a team sport.”
 In fact, Derek knew how to play a team sport, baseball, better than
any other kid in Kalamazoo. He could hit, field, run, and throw the ball
from shortstop with more power and accuracy than any pitcher could
throw it from the mound.
 Derek would play all day, any day, for as many weeks and months as
the Kalamazoo climate would allow. Of course, those summer days in
West Milford and Greenwood Lake were best spent throwing around
the ball, too, at least when Derek was not busy swimming in the lake
with his younger sister, Sharlee.
 The alternative? No, Derek did not take to the alternative work with
his grandfather at Queen of Peace, especially when the chores involved
a lawn mower and a wide-open field of unruly grass.
 Over time Sonny Connors had grown close to Charles Jeter; the
church handyman had gotten past his concerns for his biracial grandkids.
But Sonny had a special bond with Derek, who lived to please
Sonny as much as he lived to please Charles.
 Sonny got a kick out of bringing his grandson to work. One day he
asked Derek to mow a Queen of Peace football field that had the overgrown
look of a Brazilian rain forest. All elbows and knees and ankles,
young Derek was no match for the job.
 “The poor kid was going crazy with it,” said Madden, the Queen of
Peace pastor. Derek was pushing the mower, emptying the bag, and
pushing it again, and it was so hot the nuns felt sorry for him. They
brought him inside, gave him a cold soda, told him to relax.
 As soon as Sonny found out his grandson was cooling offand catching
his breath, he ordered Derek to get back to work.
 Sonny did not believe in fifteen-minute breaks, weekends, vacations,
or holidays. “We used to open presents on Christmas Eve,” Sharlee
would say, “because our grandfather worked every Christmas Day.”
 Sonny did not want his children using the word can’t in his home,
and his daughter imposed the same ordinance on Derek and Sharlee.
So when children laughed at Derek’s claim that he would be a Yankee,
and when teachers advised Charles and Dot to steer their son toward a
more realistic goal, the Jeters did not budge.
 No, the black social worker from Alabama and the white accountant
from New Jersey would not listen to people tell them Derek could not
be a big league ballplayer any more than they would listen to those who
told them they should not marry for the sake of their children-to-be.
 Derek refused to acknowledge those who thought he was banking
on a fairy tale. “People laughed at it, and I just shrugged it off,” he
would say. “It just made me work harder.”
 The Jeters built their social lives around the ball field, particularly
the Kalamazoo Central High School field just beyond the perimeter
of their backyard. When Dot was not throwing Wiffle balls for Derek
to hit in that yard, mother, son, father, and daughter were scaling the
fence to take infield and batting practice. Derek hit his baseballs, and
Sharlee hit her softballs.
 “Some people go to the movies for fun,” said Sharlee, who was Der-
ek’s athletic equal. “We went to the field. It was all part of being very
 They lived something of a Rockwellian existence in their modest
home on 2415 Cumberland Street, where Charles and Dorothy enjoyed
watching The Cosby Show with their son and daughter, and where they
maintained order by signing their children to binding behavioral pacts.
Derek signed his just before going offto high school, and the provisions
covered phone calls, television hours, homework, grade-point
averages, curfews, drugs and alcohol, and respect for others.
 Even back then Derek was one to live up to the terms of his deals.
His teachers described him as industrious, self-motivated, and willing
to lend a hand to a student in need.
 “He epitomized what every mom wants in a son,” said Shirley Garzelloni,
Derek’s fourth-grade teacher at St. Augustine.
 Discipline and accountability were the laws of the Jeters’ land.
Charles was a full-time student by day, a drug and alcohol abuse counselor
by night, and even with Dot drawing her accounting paycheck,
money had to be spent judiciously.
 One day Derek announced he wanted a pair of $125 basketball shoes
he thought would improve his modest (at the time) leaping ability. His
mother agreed on one condition: Derek had better wear those shoes
and work on his jumping 24/7.
 Sure enough, Derek would run and hop all over the family’s small
living room. “He knew it was important for us,” Dot would say, “that if
we were going to sacrifice $125, then he was going to give us his all.”
 On the field and in the classroom. By the eighth grade Jeter was
a straight-A student who maintained his popularity with students of
both genders. The boys were in awe of his athleticism, “and the girls
were in awe of his personality and looks,” said Chris Oosterbaan, his
creative writing and history teacher. “There were many crushes on
Derek Jeter.”
 The attention did not swell Jeter’s head beyond the margins of his
signed conduct clauses. Truth was, Derek would have signed anything
as long as he was allowed to play baseball for the teams that would have
him. And there was not an amateur team within a fifty-mile radius of
Kalamazoo that did not want Charles Jeter’s boy as its shortstop.
 Derek was not anyone’s idea of a braggart, but he had been telling
classmates and teachers he would grow into a big leaguer as far back
as fourth grade, inside Garzelloni’s class in the basement of St. Augustine.
Garzelloni asked her twenty students to declare their future
intentions, and she heard the typical answers from most — doctor, firefi
ghter, teacher, professional athlete.
 Only Derek was not planning on being just a professional athlete;
he had something far more specific in mind, a vision he shared with his
parents as a child. He told Garzelloni’s class he was going to be a New
York Yankee, and the teacher told the student her husband — a devoted
Yankee fan — would be happy to hear it.
 Derek did not make this some grand proclamation; he just said it
as if he were announcing his plans for lunch. “And if he said he was
going to do something,” Garzelloni said, “Derek was the kind of kid
who did it.”
 Derek told anyone who would listen that he would someday play
shortstop for the Yankees, the team his father had hated in his youth.
Before Charles started rooting for the local Tigers, he was a National
League fan from the South who did not celebrate Yankee dominance;
the Yanks were among baseball’s last all-white teams before promoting
Elston Howard eight years after Jackie Robinson’s debut at Ebbets
 Grandma Dot converted Derek on those summer trips to the castle
and lake. She took her grandson to his first Yankee Stadium game
when he was six, and years later Derek could not remember the opponent
or the final score. “All I can tell you,” he would say, “is everything
was so big.”
 As big as the boy’s ambition. Derek would stir his grandmother
at dawn, throw on his Yankee jersey, and beg her to play catch in the
yard. She always agreed, even if she knew Derek’s throws would nearly
knock her to the ground.
 Soon enough Derek entered Kalamazoo Central High on a mission
— to honor his own prophecy, the one laid out for him by his St.
Augustine classmates in a 1988 graduation booklet that included forecasts
of what the students would be doing ten years later. “Derek Jeter,
professional ball player for the Yankees is coming around,” one entry
read. “You’ve seen him in grocery stores — on the Wheaties boxes, of
 As it turned out, Jeter made his ninth-grade mark with a basketball
before he made one with a baseball. Around Halloween in ’88, Derek
was dribbling a ball up and down and around a Kalamazoo Central
service road just when Clarence Gardner was starting a road trip with
the Central girls basketball team (Michigan girls used to play their basketball
season in the fall).
 The players pressed their noses against the bus windows and expressed
wonderment over the freshman’s commitment in the face of
a late October chill. “They were all saying, ‘You know he’s going to be
great,’ ” Gardner recalled. “Of course, some of them were talking about
how cute he was, too.”
 It was the first time Derek Sanderson Jeter was known to have impressed
a busload of schoolgirls.
 It would not be the last.

Table of Contents

Introduction ix
1. The Kalamazoo Kid 1
2. The Draft 21
3. E-6 47
4. Rookie of the Year 73
5. Champion 97
6. Perfection 124
7. Dynasty 147
8. The Flip 178
9. New Guys 209
10. Alex 244
11. The Great Divide 273
12. Moment of Truth 299
13. Rebirth 331
Epilogue 364
Acknowledgments 379
A Note on the Author’s Interviews and Sources 382
Bibliography 388
Index 390

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