Episode 6: Zippy Chippy—Legendary Loser to Champion of Champions

Zippy Chippy: Legendary Loser to Champion of Champions

Zippy Chippy ran 100 races and lost 100 times. But he was a star, one of People magazine’s 50 Most Intriguing People. And so many fans bet on him that he routinely went off as the favorite. Now, in retirement, champion thoroughbreds who earned millions of dollars owe their lives to this ornery old cuss.

Zippy ChippyZippy Chippy ran 100 races and lost 100 times. But he was a star, featured in People magazine and on “Good Morning America,” among many others. So many fans bet on him that he routinely went off as the favorite. Most of those fans didn’t know that Zippy was hardly a lovable underdog who goshdarnit gave it his all but wasn’t good enough.

“Nobody got too close to him,” says William Thomas, author of the horse’s biography: The Legend of Zippy Chippy. “Even the grooms and the hotwalkers were very leery.”

Listen: Apple Podcasts | SpotifyStitcher | Overcast (links soon!)

Zippy was, and at 26 still is, an ornery cuss. He’s been known to bite, and he once caught his owner and trainer, the late Felix Monserrate, by the back of his jacket and held him suspended in midair for 15 minutes. Track workers came running at the sound of Monserrate’s screams, but they weren’t able to help him. They were laughing too hard.

Zippy Chippy had a champion’s bloodlines. He’s a direct descendent of Man o’ War, three Triple Crown winners and the greatest broodmare of the 20th century, La Troienne. Bloodlines are everything in thoroughbred racing, but Zippy Chippy parlayed that advantage into a career of futility that began at Belmont Park in New York but ended at fairground tracks in Massachusetts. His career winnings were about $30,000.

Zippy Chippy lives now at Old Friends at Cabin Creek, a thoroughbred retirement farm in upstate New York whose owner, Jo Ann Pepper, refers to herself as Zippy’s mom. And here’s the twist: Zippy is so popular that, through donations and merchandise sales, his presence pays for the upkeep of a small herd of horses who won millions of dollars and stood in the winner’s circle at major races.

“This is the most beautiful irony of any story I’ve ever come across,” Thomas says.

As you’ll hear in the story, what happens to thoroughbreds when they come off the track is a serious issue in the racing industry. The Old Friends retirement farms are supported entirely by donations, volunteer work and merchandise sales. Please consider donating or, if you’re in the area, volunteering. Visit OldFriendsEquine.org to learn how you can help these magnificent animals.

This summer Can’t Win 4 Losing visited Zippy, his caretakers and his fellow retirees, including his bosom buddy, Red Down South. Click on Zippy’s smiling face for a gallery.

Zippy's face

Note: All links to Amazon on this page are affiliate links, meaning we get a fee if you use the link to make a purchase.

Music

Opening Theme: “Big Swing Band” by Audionautix. (CC by 3.0)
Closing Theme: “Can’t Win For Losing” by Johnny Rawls, courtesy of Deep South Soul Records. Visit Johnny Rawls’ website and Facebook page.

His latest album is called Waiting For the Train.

Other Songs Used

“William Tell Overture” by Rossini
“Ipanema Daydream” by Bird Creek
“The Creek” by Topher Mohr and Alex Elena
“Dreamland” by the 126ers
All are either public domain or used under a Creative Commons license.

Learn more

 

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

Episode 5: Breaking Up — San Diego’s Life After the Chargers

Breaking Up: San Diego’s Life After the Chargers

One of the most painful ways to lose in sports is a city losing its team. San Diego Chargers fans were heartbroken when their team moved to Los Angeles. But not all of them. Maya Kroth reports from San Diego. Plus: King Kaufman on one of several teams that have left St.

Johnny Bolt PrideOne of the most painful types of losing in sports is when a city loses its team. San Diego Chargers fans were heartbroken and angry when their team moved up the freeway to Los Angeles this year. They burned jerseys and threw eggs at the team headquarters.

But not all of them. “Not having the NFL be in your city is a win,” said writer and sports commentator Dallas McLaughlin. “There’s no way it’s not.” With the Chargers struggling to convince an indifferent L.A. to pay attention to them, Maya Kroth reports from San Diego now that the Bolts have bolted.

Listen: Apple Podcasts | SpotifyStitcher | Overcast (links soon!)

Plus: The St. Louis Browns check off two boxes for this show. Their city lost them when they left town and became the Baltimore Orioles after the 1953 season, and in their half-century in the Lou, they were consistent losers.

You’d have to be at least 70 or so to even remember the Browns existing. But there’s still a St. Louis Browns fan club, and the guy who runs it, Emmett McAuliffe, isn’t even 60. Host King Kaufman talks to him about the appeal of a team he never saw — at least not before the Orioles wore throwback Browns uniforms during a road series against the Cardinals in 2003.

Also, author Burton Boxerman talks about growing up as a Browns fan, and how, once they left, he had to find a new team to root for and he picked the Chicago Cubs, because their relentless losing reminded him of his beloved Brownies.

And Ed Mickelson, 91 years old and one of 14 living former Browns, talks about his brief but memorable time at Sportsman’s Park. He wasn’t a Brown for long, but he did drive in the last run in the team’s history. It was the only run they scored that day as they went down to their final defeat.

Note: All links to Amazon on this page are affiliate links, meaning we get a fee if you use the link to make a purchase.

People in the episode

Chargers

Maya Kroth is a freelance print and audio reporter based in Mexico City. She’s available now for reporting on the aftermath of the Mexico City earthquake. You can find her work at mayakroth.com. Editors seeking coverage should contact her via Facebook messenger.

Dallas McLaughlin is a writer and performer in San Diego. His debut standup album is called An Evening of This!

Matthew T. Hall (referred to as Matt Hall in the story) is the editorial and opinion director at the San Diego Union-Tribune.

John Abundez, pictured above, is a lifelong Chargers fan better known as Johnny Bolt Pride. He says he has never worn a jersey with an owner’s name on the back. He roots for his team, and remains a Chargers fan even though they’ve moved to Los Angeles.

C-Siccness is a San Diego hip-hop artist whose song “Save Our Bolts” was used in this episode with permission.

Maya Kroth
Kroth
Dallas McLaughlin
McLaughlin
Matthew T. Hall
Hall
C-Siccness
C-Siccness

 

 

 

 

Browns

Emmett McAuliffeEmmett McAuliffe is an intellectual property lawyer in St. Louis and a member of the board of the St. Louis Browns Historical Society. His law office is filled with Browns memorabilia. Click his photo for a gallery.

 

Burton BoxermanBurton Boxerman is the author, with his wife, Benita Boxerman, of many books about baseball history and other subjects, including Jews and Baseball, Volume 1 and Volume 2; and Ebbets to Veeck to Busch: Eight Owners Who Shaped BaseballThey are working on a biography of Bill DeWitt Sr., who was a Browns executive and owner, and the father of the current Cardinals owner, Bill DeWitt Jr.

Ed Mickelson is one of 14 living former St. Louis Browns. He was a first baseman who spent the last few weeks of the 1953 season with the Browns, driving in the last run in team history during a 2-1, 11-inning loss to the Chicago White Sox on Sept. 27, 1953. Mickelson, 91, had a solid, 11-year career in the minor leagues and played briefly in the big leagues for the Cardinals and the Cubs in addition to his stint with the Browns.

After retiring from baseball, Mickelson was a football and baseball coach and a counselor in St. Louis-area high schools, retiring in 1993. His 2007 memoir, Out of the Park: Memoir of a Minor League Baseball All-Star, is notable for its honesty about his post-career depression. This photo from a Browns Reunion Luncheon on Sept. 26, 2017, shows Mickelson, left, talking to his friend and the most famous living ex-Brown, Don Larsen.

Ed Mickelson and Don Larson
Photo courtesy of Julie Mickelson Drew.

Music

Opening Theme: “Big Swing Band” by Audionautix. (CC by 3.0)
Closing Theme: “Can’t Win For Losing” by Johnny Rawls, courtesy of Deep South Soul Records. Visit Johnny Rawls’ website and Facebook page.

His latest album is called Waiting For the Train.

Other Songs Used

“Movie Piano Theme” by EK Velika
“St. Louis Tickle” by Heftone Banjo Orchestra
“Hot Swing” and “Gaslamp Funworks” by Kevin McLeod
Used under the CC BY 3.0 Creative Commons license.

 

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

Episode 4: At Long Last – The Cavaliers, the Warriors and the Cubs

At Long Last: The Cavaliers, the Warriors and the Cubs

You spend a lifetime as the long-suffering fan of a losing team. It shapes who you are. And then: They win it all! Authors Scott Raab (“The Whore of Akron,” “You’re Welcome, Cleveland”) on the Cleveland Cavaliers and Barry Gifford (“In the Neighborhood of Baseball,” “Wild at Heart”) on the Chicago Cubs.

LeBron James
LeBron James (Photo: Keith Allison/CC BY-SA 2.0)

You spend a lifetime as the long-suffering fan of a losing team. It shapes who you are. And then: They win it all! Authors Scott Raab (The Whore of Akron, You’re Welcome Cleveland) on the Cleveland Cavaliers and Barry Gifford (The Neighborhood of Baseball, Wild at Heart) on the Chicago Cubs. Plus: Host King Kaufman visits yet another championship parade for his once-hapless Golden State Warriors.

 

Listen: Apple Podcasts | SpotifyStitcher | Overcast (links soon!)

Note: All links to Amazon on this page are affiliate links, meaning we get a fee if you use the link to make a purchase.

Scott Raab
Scott Raab
Barry Gifford
Barry Gifford, 2006

I interviewed Barry Gifford at his writing studio in Berkeley, Calif., the in-law apartment of a house he owns there, and Scott Raab in the attic of his house in Glen Ridge, N.J. In both cases, I made the rookie podcaster mistake of forgetting to ask if I could take a photo. I had a quick selfie Raab had texted me so I would recognize him when he picked me up at the train station. I told him I realized that probably wasn’t for public consumption and asked if he wanted to send me a different photo. So he sent me a different quick selfie. The Gifford photo is by Tabercil (Creative Commons CC BY 2.0).

Read and watch more

Warriors Championship Parade

Warriors parade
A vendor at the Golden State Warriors championship parade in Oakland, June 15, 2017. Click for a gallery of photos from the parade.

Music

Opening Theme: “Big Swing Band” by Audionautix. (CC by 3.0)
Closing Theme: “Can’t Win For Losing” by Johnny Rawls, courtesy of Deep South Soul Records. Visit Johnny Rawls’ website and Facebook page.

His latest album is called Waiting For the Train.

Other songs used

Cavaliers
“On My Life” by Letter Box
“Walking the Dog” by Silent Partner
“Bluebird” by E’s Jammy Jams
“Down n’ Dirty” and “Right to Be” by Jingle Punks
Cubs
“Sing Swing Bada Bing” by Doug Maxwell, Media Right Productions
“Bar Crawl” by JR Tundra

 

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

Episode 3: Casey Stengel — How to Learn By Losing

Casey Stengel: How to Learn By Losing

With the Yankees in the ’50s, he had the greatest run in managerial history. But before that, Casey Stengel skippered a series of relentlessly terrible teams. Host King Kaufman asks: Did the Old Perfessor learn to win by losing?

Casey Stengel
With the Yankees in the ’50s, he had the greatest run in managerial history. But before that, Casey Stengel skippered a series of relentlessly terrible teams. Host King Kaufman asks: Did the Old Perfessor learn to win by losing? Plus: What if the worst player on the worst team in a league met the best player on the best team in that league 40 years later? And what if one of those guys was the host of a podcast about losing?

Listen: Apple Podcasts | SpotifyStitcher | Overcast (links soon!)

Casey Stengel
Stengel in 1935, his second year as manager of the Brooklyn Dodgers. They finished fifth.
Casey Stengel
Stengel in 1938, his first year as manager of the Boston Bees. They finished fifth.

 

 

 

 

 

 

 

 

Casey Stengel managed the Brooklyn Dodgers from 1934-36 and the Boston Braves from 1938-43. The Braves were known as the Bees from 1936-40. Stengel’s teams in Boston and Brooklyn went 581-742, a .439 winning percentage, and never finished higher than fifth in the eight-team National League.

Note: All links to Amazon on this page are affiliate links, meaning we get a fee if you use the link to make a purchase.

People in the story

Steven GoldmanSteven Goldman is a baseball columnist for FanRag Sports and the author of Forging Genius: The Making of Casey Stengel. He is also the host of The Infinite Inning podcast. He was a pioneer of the blog format with his long-running The Pinstriped Bible, and was the editor and co-writer of the books Mind Game, It Ain’t Over ‘Til It’s Over and Extra Innings: More Baseball Between the Numbers. He was editor in chief of Baseball Prospectus and edited seven editions of the Baseball Prospectus annual.

Marty AppelMarty Appel is a longtime baseball author, publicist and historian and the author of the 2017 biography Casey Stengel: Baseball’s Greatest Character. He was George Steinbrenner’s first public relations director with the Yankees, the youngest person ever to hold that position for a major league team. He’s also led public relations for WPIX in New York and the Atlanta Olympic Committee. His many other books include Pinstripe Empire: The New York Yankees from Before the Babe to After the Boss and Slide, Kelly, Slide, a biography of Mike “King” Kelly, who was mentioned in Episode 1.

Steve JacobsonSteve Jacobson was a reporter and columnist for Newsday for four decades. He covered Stengel when the Old Perfessor was manager of both the Yankees and the Mets. He’s the author of several books, the most recent of which is All Bets Are Off with Arnie Wexler, about Wexler’s life as a gambler.

2nd story: Extreme Little League

Vince Beringhele
Vince Beringhele.

At 7, I was the worst player on the worst team at North Venice Little League in Los Angeles. I’ve told this story before, including the part about how the funky rules forced me to play as officially one year older than I really was. The dominant player in that league was a kid named Vince Beringhele. When he was 11, coaches around the league were talking about how he’d probably play pro ball someday. We were the extremes of the league.

He did play pro ball. He spent three years in the Dodgers organization before knee injuries ended his career. I decided to try to talk to him. He’s the head baseball coach at Cal State Los Angeles, and I caught up with him as he was getting his team ready for the 2017 conference tournament in Stockton, California. He was a lot less scary than when I was trying to hit against him!

We talked about how in sports, everybody, even the best player in the league, loses eventually.

Music

Opening Theme: “Big Swing Band” by Audionautix. (CC by 3.0)
Closing Theme: “Can’t Win For Losing” by Johnny Rawls, courtesy of Deep South Soul Records. Visit Johnny Rawls’ website and Facebook page.

His latest album is called Waiting For the Train.

Other songs used

“Aces Hight” and “AcidJazz” by Kevin McLeod (CC BY-SA 3.0)

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

Episode 2: The Stanley Can—The Washington Capitals and the Worst Season Ever

The Stanley Can: The Washington Capitals and the Worst Season Ever

The Washington Capitals were the worst team in NHL history in their inaugural year. By late March they’d played 37 road games without earning so much as a point, and they’d lost 17 straight overall. Then they got a win.

Washington Capitals goalie Ron Low
Ron Low

The Washington Capitals were the worst team in NHL history in their inaugural year. By late March they’d played 37 road games without earning so much as a point, and they’d lost 17 straight overall. Then they got a win. “The reaction was totally frickin’ crazy,” says goalie Ron Low, who with teammates Ron Lalonde and Jack Lynch helps tell the story of the Stanley Can Caps. Plus: The No Whine Timeline lets you know when it’s OK to complain about your lousy team.

 

Listen: Apple Podcasts | SpotifyStitcher | Overcast (links soon!)

People in the story

Ron LowRon Low was the starting goalie for the 1974-75 Capitals. His record was 8-36-2 with a 5.45 goals against average, more than two goals above league average. “If that would have ever bothered me,” he says about that figure, “I would have liked to quit hockey.” Low, who was in his second year in ’74-75, spent 13 years in the NHL with the Toronto Maple Leafs, Washington Capitals, Detroit Red Wings, Edmonton Oilers and New Jersey Devils. He had a long career as an assistant coach and scout and was the head coach of the Oilers from 1994-99, and the New York Rangers from 2000-02.

Ron LalondeRon Lalonde was a third-year center who was traded from the Red Wings to the Capitals on Dec. 14, 1974. He played that season and four more for the Caps before winning an American Hockey League title with the Hershey Bears in his last year as a player. He’s been a financial planner and investment counselor for 36 years.

Jack LynchJack Lynch was a defenseman in his second year in the league when he was traded from the Pittsburgh Penguins to the Caps on Feb. 8, 1975. He sustained a devastating knee injury in 1977 and was never the same player. Like Lalonde, he played with the Capitals through 1979. He is now retired after a long career in public and media relations with the Ontario Ministry of Tourism and Recreation.

Career stats: Low | Lalonde | Lynch — (Courtesy Hockey-Reference)

Historical Figures

Milt SchmidtMilt Schmidt was the general manager of the expansion Washington Capitals. He had been a Hall of Fame center for the Boston Bruins, a member of the famed Kraut Line. He won Stanley Cups in 1939 and ’41 and the Hart Trophy, the NHL’s Most Valuable Player award, in 1951. He coached the Bruins for 11 seasons before becoming general manager in 1967. He was the architect of two Stanley Cup-winning teams in Boston before taking the Capitals job in 1974. He died in January 2017 at the age of 98.

Read More

Music

Opening Theme: “Big Swing Band” by Audionautix. (CC by 3.0)
Closing Theme: “Can’t Win For Losing” by Johnny Rawls, courtesy of Deep South Soul Records. Visit Johnny Rawls’ website and Facebook page.

His latest album is called Waiting For the Train.

Note: All links to Amazon on this page are affiliate links, meaning we get a fee if you use the link to make a purchase. 

Other songs used

“D.J.” by Jahzzar (CC BY-SA 4.0)
“Disco High” by UltraCat (CC BY-SA 3.0)
“Hustle” by Kevin McLeod (CC BY-SA 3.0)

 

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.