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May 5, 2018 16 mins

Today's episode revisits the story of Jimmy Winkfield, who won the Kentucky Derby twice. When this podcast was published originally, he was the last African-American jockey to win the race. Winkfield moved abroad in 1904 to continue his career, but it wasn't until 2005 that Congress honored his work. 

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Episode Transcript

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Speaker 1 (00:02):
Hey, I hope everybody is having a great weekend. It
is Kentucky Derby weekend, so we thought this might be
a good time to revisit previous hosts Sarah and Deblina's
episode from eleven on Jimmy Winkfield, who won the Kentucky
Derby twice and no other black man has won the
Derby since. We also talk about the Derby in our

(00:22):
episode the Kentucky Derby's First fifty Years, which you can
find in our archive if you want some more Derby
stories today, So put on your fancy hat and enjoy.
Welcome to Steph you missed in history class from house
stuff works dot com. Hello, and welcome to the podcast.

(00:49):
I'm to blame a choko reboarding and I'm say and
the Kentucky Derby is coming up on May seven, and
so I thought this would be an okay time to
confess that I have an inexplicable bowl fascination with horse racing.
Really surprised me about you you told me this earlier
in the day. Yeah, I don't even know what it is.
It's not like I mean, I've ridden horses before, but

(01:10):
I wasn't really very much into it growing up. I
had some friends who were, but even they weren't into racing,
so I don't really know what it is except for
just the stories behind the jockeys, behind the horses and
the trainers. It always seems whenever I tune into the
Kentucky Derby every year, I hear all these stories of

(01:30):
triumph over adversity, and I don't know great comebacks. I
imagine you have like a secret hat collection you bring
out for the Kentucky Derby, Sarah, I only wish. But
before we go any further, for those who aren't familiar
with the Derby, it's one of the classic American horse
races and probably the most widely known in the US.

(01:51):
It started in eight seventy five and it takes place
annually the first Saturday in May at Churchill Downs in Louisville, Kentucky.
The race stist In says about one point to five
miles one mile and a quarter and it's often called
the most exciting two minutes in sports. Yeah, and like
I mentioned, we do associate things like big hats with
the Kentucky Derby, mint juleps, high rollers, that kind of thing.

(02:14):
It's a very elite event and at least in the
last one hundred years or so. It's not that racially diverse.
Certainly that's not the way you think of it. But
as we're gonna learn, there was a time in the
early days of the Derby when African American jockeys dominated
the US horse racing scene. Yeah, and so here we're
going to talk about the last black jockey to win

(02:36):
the Kentucky Derby, Kentucky native actually, whose name was Jimmy Winkfield.
And we'll take a look at his short but successful
US career and the events that brought that to a close,
and his remarkable experience as abroad. But first, um, we
want to look a little bit at this history of
African Americans and horse racing, so we can trace African

(02:58):
Americans participation in this board to colonial times when the
British brought their passion for horse racing to America, and
according to an article in The Smithsonian by Lisa Kay Winkler,
even founding fathers George Washington and Thomas Jefferson frequented the track,
and former President Andrew Jackson had his own thoroughbreds and
black jockeys so very much a part of our an

(03:19):
illustrious start but the first black jockeys were slaves, and
they got their skills and their affinity for horses, their
connection to horses from doing sort of the menial we're
cleaning the stables or grooming the owners valuable animals. And
Winkler points out that being on the racing circuit once,

(03:39):
once black jockeys did start making it big, gave them
a sort of false sense of freedom. It was one
of the few ways that they could achieve real status,
and a lot of them did. They went all the
way to the top in American horse racing. In the
first Kentucky Derby in eighteen thirteen, out of fifteen jockeys
were black, and among the first twenty eight Derby winners,

(04:02):
fifteen of them were black. So they were they were
dominating the horse racing scene. Yeah, exactly. And this was
the environment that James Winkfield was born into on April twelfth,
eighteen eighty two, in Kentucky, and he was the youngest
son of George and Victoria Winkfield, who had a total
of seventeen kids. They were farmers, basically sharecroppers, and lived

(04:22):
in a shotgun shock so some of the kids actually
had to spill out on the porch at night to sleep. Yeah,
but little James definitely got interested in horses and racing early,
probably in no small part because he was growing up
in bluegrass country and he heard he probably saw the
horses and also heard the stories of black jockeys making

(04:42):
a name for themselves and getting big, and lucky for him,
he didn't get big. He's stayed small, which is of
course a requirement for professional jockeys. Even though he had
some siblings who were six ft tall, this is quite
a discrepancy because by his teen years he was only
five ft tall and less than one pounds, so perfect
build for a jockey. Yeah. And he started out just

(05:05):
bugging other groomers in his area until they finally gave
in and let him do some of their work for free.
Sounds like a pretty good deal to me if you're
one of those workers. But Jimmy then got hired on
as a groomer and an exercise boy, so he got
his own gig and this is how he got his
experience in training and kind of got discovered just riding
horses as an exerciser. And there were some trainers who

(05:27):
were looking out for opportunities all the time. To turn
riders into jockeys, looking for people who just seemed to
have that natural talent. And that's how Jimmy got his
first break in at age sixteen. Yeah, so he rode
a race at Chicago's Hawthorn race Course. But it didn't
turn out to be the big break he was really
looking for it. In fact, it was quite a disaster.

(05:48):
His horse broke next to last at the start, and
then when he thought he saw an opening, he broke
fourth from the rail and cut across the path of
three horses and he took them all down in the
process and got suspended for a year because of it.
He came back though in eighteen nine, strong as ever. Yeah,
he started winning races in Chicago. For example, in nineteen

(06:09):
hundred he rode in his first Kentucky Derby, and that
was out of four races four Kentucky Derby races. I
should say that he would ride in total. In nineteen
hundred he placed third. The next two years he placed
first in the Kentucky Derby, first on a horse called
His Eminence and then on Allan a Dale, And this
made him only the second jockey to win two successive

(06:29):
Derby's and I mean there's still really aren't that many
jockeys who can claim that our feet indeed, and in
nineteen o three he finished second because he made his
move too soon, and it was a loss that always
bugged him. I mean, he was hoping to go for
three in a row there, it seems. Yeah, I've read
that he actually talked about that loss until his death.
You know that he should have won it, Yeah, the

(06:49):
one that going away. So by that time, the US
horse racing scene was already changing thanks to racism, segregation,
Jim Crow laws and the economy me played a part.
Two recessions at the time really shrunk the number of
race tracks and the attendance at the race tracks that
were still open. And they were also anti gambling groups
going around, so that was further shutting down the number

(07:12):
of race tracks that were operating. Yeah, definitely, they went
down from three fourteen tracks in eighteen ninety to twenty
five by nineteen o eight, so really big dive and
white jockeys also didn't like competing with black jockeys for
the best mount so at times there was outright violence.
I mean during races on the track, black jockeys would

(07:32):
sometimes we pushed towards the rail um. There was even
a riot in Chicago between the white and the black jockeys. Yeah,
so times were definitely changing, and you can really tell.
Even though Winkfield one more than one hundred and sixty
races in nineteen o one, Goodwin's annual Official Guide to
the Turf admitted his name, so he he wasn't even
a player even anymore, even though he was still winning. Yeah,

(07:56):
and perhaps more seriously, or definitely more seriously, I should say,
he received death threats from the ku Klux Klan. So
it was getting really hard for a black jockey to
work in the United States anymore. And all those reasons

(08:18):
were contributing for sure. But he really sort of put
the final nail in his own coffin for his US
career because in nineteen o three, he was scheduled to
ride for one owner in the Futurity Stakes in New
York City and then he accepted a three thousand dollar
offer to switch horses and ride on the favorite. And
this was a big faux pot. I mean, as you

(08:40):
can imagine, switching horses at the last minute, and it
really hurt his reputation. Yeah, so after the horse switch incident,
Winkfield's number of rides dropped by a third. So he
ended up moving to Russia in nineteen o four, where
he accepted a position with an American owned stable, and
there his career really took off again. His first year
there he won the Czar's trip Crown, which is the Moscow,

(09:01):
the St. Petersburg and the Warsaw Derby's and he was
also the nineteen o four Russian national writing champion. Yeah,
and over the years he just kind of kept on,
winning the Moscow Derby four more times on one horse alone,
and then several other times on different mouths. He rode
on and off for different owners of Polish Prince the
German Baron, so he wasn't just riding in Russia. He

(09:25):
was riding in Austria and Germany and France too, and
making a lot of money doing it. Yeah. His salary
at one point was seventeen thousand roubles, so it would
have been equal to about eight thousand, five hundred dollars
at the time per year, plus ten percent of every
purse that he won, so he was pretty well off
to say the least. He was living in this fancy

(09:46):
schmancy hotel, the National hotel in Moscow and having caviare
for breakfast. As we know, though, by nineteen seventeen or so,
there was trouble brewing in Russia and the Bolsheviks and
the Communists are getting organized, and the racing community was
really at risk because it was something that rich people did.
It was a symbol of the aristocracy, and so Winfield,

(10:09):
to protect himself had to walk around in tattered clothing
to avoid getting arrested by Bolsheviks. I still think that's
quite I don't know, it's it's hard to imagine this
five foot tall guy walking around and what did they
think of him? Like he would still stick out? I
think definitely. He was working in Odessa for Prince Louma,

(10:31):
miss Key of Poland and nineteen nineteen when the Russian
Revolution finally caught up to him, when they started hearing
the sound of cannons, he and the rest of the
racing community, which included horsemen and their families and about
two fifty two and sixty horses something in there, they
all took off an escaped to Poland. It was a
really hazardous journey one thousand, one hundred miles to Warsaw.

(10:53):
They had to cross the Transylvanian Alps, and they had
to actually unfortunately eat some of the horses along away
because they got desperate for food. But they did make
it eventually. Yeah, and once he was in Poland, Wingfield
again resumed his riding career and started to recoup his fortune,
most of which he lost when he left Russia. Even

(11:14):
though he was getting older, he did become a successful
writer again. He continued as a jockey through the nineteen twenties.
He won several stakes races and altogether he ended up
winning two thousand, six hundred races in his entire riding career.
That was one amazing thing I thought about this story.
I kept expecting some sort of sad end, but he

(11:37):
keeps bouncing back time after time. He does. In two
even when he was as he was building up his
racing again and still writing, he built a stable in
a home near Paris in Mason Lafitte. He had a
little family there with him too, by then, a son
and a daughter with his third wife, who was an
exiled Russian aristocrat named Lydia de Mickowitz. So when he

(11:58):
finally retired from writing in nine teen thirty, around the
age of forty eight, he decided to devote his life
entirely to training horses at his stable in France, so
he stayed put there, settled there instead of traveling around
racing all the time, and he trained his own horses
and horses for other owners too, and he ended up
doing really well by it. But unfortunately he loses his

(12:19):
fortune once again when the Germans invade France in ninety
one and the Red Cross evacuates his family to the US.
He's home, so he's back home again. And black jockeys
had pretty much disappeared from the racing scene by the
early twenties, and Winkfield was looking for work and signed
up with the Works Progress Administration working on a road

(12:40):
crew and later had to work as a groom and
an assistant trainer for a living, So I mean a groom.
That's back to where he where he started as a kid. Finally, though,
he got to return to France in nineteen fifty three
and start up his operation, his racing and training stable again,
and he died in France March nineteen seventy four at

(13:01):
age one, again just bouncing back. It's so impressive that
he had he had it in him to keep going
and try again. Yeah. It was a phenomenal life and
a phenomenal career really and very impressive. But it took
Winkfield a long time to get recognition that he deserved
in his home country. In the US, there's a story
that's often told about he and his daughter attending the

(13:24):
nineteen sixty one Kentucky Derby. Actually it's really sad. They
were invited to a Sports Illustrated event, a dinner at
the Brown Hotel in Louisville, but they almost got turned
away at the door by the doorman, and they had
to have him go check several times and insists that
they were guests and they were supposed to be there,
and they finally got in. But then even when they
did get there, they were essentially ignored by the people

(13:46):
at the dinner. The dinner kind of the people at
the dinner kind of came up to them and said
high and shook hands, and then they didn't talk to
anyone the rest of the time. His daughter said in
a two thousand two NPR Weekend Edition interview that the
only person who talked to us was a previous jockey
who had won the derby, and that was Roscoe Goose.
He was the only one who was friendly enough to

(14:06):
talk to us. Nobody else talked to us the whole time.
That's so sad and tragic and disappointing. I guess, very
that's the perfect way to describe it. Disappointing, And I
think you mentioned that. I thought this was a neat
counterpoint to it. Even though he's so disrespected at this event,
he said he still really enjoyed the race because that's

(14:28):
his element. He liked it, he liked being there. Again, Yeah,
from what I've read, he really enjoyed being at the
race and kind of didn't care that people had treated
him that way, or really didn't seem to care. I
guess because he had been through so much in his
life anyway, Transylvanian Alps probably puts things in perspective. Yeah,
that would definitely change your perspective on the whole thing.
I think that he was more embarrassed and worried about

(14:49):
his daughter in that situation, necessarily than himself. But regardless,
things have changed a lot over the past decade. Wingfield
finally got inducted into the National Racing Hall of Fame
in two thousand four, and in two thousand five, the
House of representatives passed a bill honoring him, and in
two thousand Marlon St. Julian became the first African American
to ride in the Derby. Since there's been a few

(15:11):
since then, so maybe things are starting to change, starting
to get back to how they were at the end
of the eighteen hundreds. Yeah, it's interesting to think of
going backwards as progress, but I guess in a weird way,
that's kind of what it would be. Maybe. Thank you

(15:32):
so much for joining us for this Saturday classic. Since
this is out of the archive, if you heard an
email address or a Facebook U r L or something
similar during the course of the show, that may be
obsolete now. So here is our current contact information. We
are at History Podcast at how stuff Works dot com,
and then we're at Missed in the History. All over

(15:52):
social media that is our name on Facebook, Twitter, Tumbler, Pinterest,
and Instagram. Thanks again for listening. For more on thiss
and thousands of other topics, visit how staff works dot com.
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