The Defining Generation
Milton Lee Olive, III
When one Black boy came into this world in Chicago on November 7, 1946, it was a day of mixed emotions for Milton Olive, Jr. The newborn child was Milton and Clara Lee Olive's first child. He was also destined to be their last; Clara Lee died four hours giving birth to a new life. The third generation in a line of Milton Olives, that infant was given his mother's middle name, becoming Milton Lee Olive, III. Throughout his life however, he would become affectionately known to his family, and years later to his comrades in the Army, as "Skipper" or "Skip".
For Milton Olive, Jr., the news on that day went from bad to worse. Not only had he lost his young wife, the prognosis for the survival of his infant son did not bode well. Doctors gave him little chance of surviving more than one or two days. But the under-weight, fragile little boy fought for life with a resolve that belied his scrawny frame. He survived those first critical days and was soon released from the hospital to the South Side Chicago home where he would grow up, with periodic visits to live with his grandparents in Mississippi.
Skipper was never a South Side Chicago hard-case like many of the young boys who had to grow up in what was often a rough side of the city. Rather, he was a quiet kid, never hanging out with neighborhood toughs or seeking trouble. That rather placid personality however, was never misunderstood as a character weakness by those who knew him. Skipper was a scrapper when circumstances demanded it; his very survival against a gloomy medical prognosis had demonstrated this vividly.
Even in those early, formative years after his birth, Skipper's health was always a matter of concern. "It wasn't until he was in the first or second grade that we began to quit worrying, and realized he would survive," recalled Barbara Penelton, his aunt, during a recent interview.
After Skipper's birth, his father relied heavily upon his extended family to help him raise the young boy. Many of Skipper's early years were spent living with relatives in Chicago or with his grandparents on their farm in Lexington, Mississippi. Then, when Skipper was ten years old, his father married Antoinette Mainor, a teacher in a Chicago public school, and young Milton moved home to live with his father and step-mother.
In contrast to his infancy where he had battled simply for life, in adolescence Skipper enjoyed a rather comfortable home life. His father doted on his only son and, unlike so many poor Black families who lived in the South, could afford to cater to his son's whims and desires. "He got new bicycles for his birthday and cameras for Christmas," wrote Don Terry in a 2002 Chicago Tribune story about the man who became a local hero. "At family gatherings, when his cousins were dressed in jeans and t-shirts, he was often decked out in a suit that matched his dad's.
"Olive loved taking photographs with his father, who made a few extra bucks snapping newlyweds and church picnics. Stuck inside the pages of his (Skipper's) Bible was a business card his father had made for him years earlier: Milton Olive III, Chicago's Only 12-year-old Professional Photographer."
Miles away from Chicago, Skipper had a "second-family" in Mississippi, and during his summer school vacations he frequently returned to his grandparent's farm. When he was ready to begin high school Skipper opted to remain on the farm. For the next two years he attended an all-Black school that was an extension of a local Pentecostal church.
While living in Mississippi Skipper could not help but become intimately aware of the glaring disparity between the rights and opportunities afforded to White men and women as opposed to their Black American counterparts. He was quickly caught up in the Civil Rights movement. During the summer between his freshman and sophomore years some 200,000 civil rights advocates marched on Washington, D.C., to hear Dr. Martin Luther King deliver his famous "Dream Speech." As he began his sophomore year trouble continued to broil in the South. On September 13, 1963, a bomb exploded at the Sixteenth Street Baptist Church in Birmingham, Alabama, a key site of many civil rights organizational meetings. The explosion killed four young girls: Denise McNair, Cynthia Wesley, Carole Robertson, and Addie Mae Collins, who were attending Sunday School that morning. The tragedy prompted immediate riots in Birmingham that resulted in the death of two more young Blacks.
On January 23, 1964, while Skipper was mid-way through his second high school year, the requisite three-fourths of the 50 United States ratified the 24th Amendment to the U.S. Constitution that had passed the Congress a year and a half earlier. While that amendment said NOTHING about the rights of Black Americans, it was in fact a sweeping reform. The Amendment reads simply:
"The right of
citizens of the United States to vote in any primary or other election for
President or Vice President, for electors for President or Vice President,
or for Senator or Representative in Congress, shall not be denied or
abridged by the United States or any State by reason of failure to pay
poll tax or other tax."
Poll Taxes had been enacted
in eleven Southern states after Reconstruction as a measure to prevent
poor people, who included the vast majority of Southern Blacks as well as
poverty-stricken and uneducated White people, from voting. While the Poll
Tax violated a provision of the 14th Amendment insuring
"equal protection under the law", and despite having been found
unconstitutional by the U.S. Supreme Court, at the time the 24th
Amendment was ratified FIVE southern states (Virginia,
Alabama, Texas, Arkansas, and Mississippi) still used the illegal tax as a
means of silencing the voice of their Black and poor White populations.
of the 24th Amendment could not have occurred at a more
opportune time. For two years the Congress on Racial Equality (CORE), the
Student Non-Violent Coordinating Committee (SNCC), and the Nacional
Association for the Advancement of Colored People (NAACP) had struggled to
strengthen the political voice of Black Americans in the South through
organized voter registration drives. The three diverse organizations found
strength in uniting under the umbrella of the Council of Federated
Organizations (COFO), and in September 1963 sponsored a highly successful election
experiment in Mississippi. The Freedom Vote was intended to
illustrate the desire of Missippi's poor black population to be involved
in the political process. More than 90,000 of them voted in a mock
election pitting candidates of an unofficial Freedom Party against the
official State Party Candidates. It set the stage for a turbulent, but
historic change in the tide of the Southern political process over the
next year in a stirring, and often dangerous, clammor for civil rights
that caught up young Skipper Olive in its enthusiasm.
became one of 3,000 students who attended one of the 50 "Mississippi
Freedom Schools" as part of the Mississippi Project led by COFO in an
effort to educate the state's Black population about their rights, and
their potential to change their society by making their voices heard at
the polls. Though these youths were too young to vote, (in the election of
1964 the National age for voting rights was 21), COFO concentrated largely
on 10th, 11th, and 12th grade students.
the traditional school year ended in the Spring of 1964 the Mississippi
project evolved into a massive voter registration campaign that was called
the Freedom Summer Project. It was an effort in which Skipper was
an ardent supporter and active participant. As project volunteers spread
out across Mississippi to visit Black homes and register new voters, they
needed "guides" to help them get around the largely rural, poor
Southern Communities. Skipper became one of those guides, despite the
danger of escalating violence.
violence was in fact, both real and extreme. On June 21, 1964, Michael
Schwerner and Andrew Goodman, two White student civil rights activists who
had come to Mississippi from Northern colleges for the summer project
disappeared. Along with them was a local CORE volunteer, a young Black man
much like Skipper Olive and only 4 years his senior, James Chaney. Though
the three men's bodies went undiscovered until August 4, it was an
immediate certainty after their disappearance that the three men had been
retaliation against the Freedom Summer Project, during June, July, and
August Mississippi's most ardent segregationists and white supremacists
burned 37 Black churchs and the homes or businesses of 30 Black families.
More than 1,000 CORE volunteers, many of them white students from Northern
universities, were arrested; 80 volunteers were viciously beaten.
the violence could not deter Skipper from his new-found mission in life,
it certainly became a concern for his grandmother. Because the young man
refused to quit his volunteer duties with the Mississippi Project, Grandma
Olive sent him back to his father in Chicago with the comment, "He's
going to get killed, and get us killed." Her fears were not
unfounded; the violence of that hot summer in Mississippi often spilled
over to destroy the family of those who sought to change America at the
Skipper returned to his father's home he was much like many 17 year old
boys, both Black and White, of any generation; shiftless, uncertain about
his future, and still seeking to find himself. His father sought to
provide guidance by offering Skipper three alternatives. The young man
could either go back to school (in Chicago), get a job and go to work, or
join the military.
Skipper opted to return to school. When he attempted to enroll for his
Junior year at Chicago's Highland High School however, he learned that
some of the credits he had earned during his first two years in a
Mississippi Pentecostal High School would not transfer. At Highland High
he would not be an upper classman scheduled to graduate in 1966. Rather he
would have to repeat much of his Sophomore year.
Skipper then turned to his father's second option. Quickly he learned that
there were few jobs available to a 17-year-old Black boy who did not have
a high school diploma. Before considering the third alternative, Skipper
borrowed money from a cousin and took a train back to Mississippi to
rejoin the Mississippi Project. Shortly after his arrival word reach his
grandmother that Skipper was back, living temporarily with a school
employee and continuing his dangerous activities in the civil rights
chain of events that wound up sending Skipper BACK to Chicago left him
feeling both disappointed in himself and embarassed in front of his
family. He had dropped out of school, joined a growing but not always
popular civil rights revolution, failed to find a job, and bounced back
and forth from one family member to another. At last, shortly before his
18th birthday, Milton Lee Olive, III, decided to prove he could
do something positive. With a cousin he joined the United States Army.
determined to prove his worth, Skipper applied for jump school in order to
become a paratrooper. He was proud of his uniform, wearing it regularly
when he came home on leave, and was doubly proud of his jump wings.
Writing home to the family he noted, "You said I was crazy for
joining up. Well, I've gone you one better. I'm now an official U.S. Army
Paratrooper. How does that grab you? I've made six jumps already."
June 5, 1965, one month after the Sky Soldiers arrived at Bien Hoa
Airfield, Private First Class Milton Olive joined the 173d Airborne in
Vietnam. Within a month he earned his first Purple Heart when he was
wounded in action, an incident he hid from his family in order to spare
them undue concern for his safety. Already back home there were subtle but
divisive whispers about the wisdom of Skipper's father having sent his
only son off to war. Milton Olive, Jr., indeed had to question his own
wisdom in that action. In his defense, it was of little comfort to him to
point out that when he had offered his son that option, there was no real
war in Vietnam and few Americans even knew that the Southeast Asian
First Class Olive was a good Sky Soldier and well liked. His somewhat
cerubic countenance, his quiet demeanor, and his tendency to avoid brash
and vulgar language made him stand apart. Combined with Skipper's
propensity to constantly quote scripture, in Vietnam he earned a second
nickname. The men of Bravo Company's third platoon often called him
Skipper made it a point NOT to communicate things that would worry his
family, such as the wound that had earned him a Purple Heart, he wrote
home regularly and not only to his father and step-mother, but to his
cousins as well. Early in October he sent a letter to the farm in
Mississippi in which he wrote, "Grandma, please send me some
cookies." In a letter penned later that same month he wrote a
poignant line reveling much of what he felt about life in the war zone. "We
all do a man's job and wear a man's clothes and call ourselves men," he
noted, "but some of us are still little boys."
as Skipper wrote those words, a package with the previously requested
cookies was on its way to Vietnam. They would not arrive in time. Weeks
later when the unopened package was returned by the Postal Service to the
farm in Mississippi, it was a traumatic moment for an aging grandmother
whose heart had already been broken.
on the morning of October 22 Army helicopters inserted Bravo Company at
the edge of the dense jungle outside Phu Cong. Quickly the heavily-loaded
troopers fanned out in a sweep towards the hidden enemy. The enemy did not
remain hidden for very long. Amid a hail of gunfire that for a time pinned
down the platoon, one of Skippers buddies was killed. The "little
boys" of 3d platoon had little time to grieve the loss of their
comrade. There was still a man's job to be done. Attacking into the
jungle, they drove the enemy backward and into retreat.
the enemy withdrew backward into the jungle, Lieutenant Jimmy Stanford
rallied his men to give chase. Following their leader, Platoon Sergeant
Vince Yrineo and three men of the 3d platoon gave chase. The three were
John "Hop" Foster, a 19-year old Black private from Pittsburgh,
Pennsylvania; 20-year old Private Lionel Hubbard, a Black kid from
Brownfield, Texas, and Private First Class Milton Lee Olive, III.
the five soldiers pursued the fleeing enemy they suddenly found themselves
racing into an ambush. An enemy bullet crashed into Foster's steel pot and
glanced downward to draw blood above his eye. "How bad is it?"
he shouted above the din of battle to his nearby comrade.
live," Milton Olive shouted back with a grin as he continued to rake
the hidden enemy with his rifle. The smile quickly vanished and Skipper
shouted again, "Look out, Lieutenant, grenade!" 
five members of 3d platoon were in a tight perimeter and the enemy
explosive might well have cost all five men their lives--but for the
subsequent actions of an 18-year old boy from Chicago. Quickly Milton
Olive reached out to grasp the deadly orb, hugging it to his body and then
falling on top of it. It exploded almost immediately, tossing the slender
paratrooper's body into the air and flipping him over on his back. Red
blood flowed from the multiple wounds of a shattered Black body, but four
men survived and continued to battle the hidden enemy. Before the contact
was broken Stanford, Yrineo, Hubbard, and Foster were all wounded. But all
four men survived to return home, raise families, and to never forget they
had been spared by the sacrifice of a comrade.
On April 21, 1966, the elder Milton Olive and his wife Antoinette were honored guests at the White House. On that day President Lyndon Johnson read a citation detailing the heroic acts of their son just six months earlier, while Lieutenant Jimmy Stanford and Private John Foster looked on. Then, with Chicago Mayor Richard Daly, members of Skipper's extended family, and other dignitaries gathered for the somber but impressive ceremony, President Johnson presented Milton Olive the Medal of Honor posthumously earned by his only son. In that moment, Milton Lee Skipper Olive, III, became the first Black soldier of the Vietnam War, and the third Black American since the Spanish-American War, to receive his nation's highest honor. He was also the first Black American in history to be awarded the Medal for actions performed while serving in a non-segregated Army combat unit.
Before the ceremony
concluded the President read a letter, revealing for the first time the
text of a letter Skipper's father had sent the President upon receiving
word that his son would receive the Medal of Honor. Milton Olive, Jr., had
 Special thanks to Don Terry and The Chicago Tribune, for permission to re-print these and other selected quotes from the May 12, 2002, article: The Men Of Olive Company; Four Soldiers Survived Vietnam Because Milton Olive Didn't
 On July 1, 1971, the 26th Amendment was ratified, lowering the voting age to 18 years of age.
 These were Milton Olive's last words as told by Jimmy Stanford. John Foster remembers events slightly differently. According to his account Olive shouted, "Look out, Hop, grenade!"
The Defining Generation: Copyright © 2006 by Doug and Pam Sterner
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