Anguilla Lit Fest Blog


Anguilla Lit Fest is a Literary Homecoming for Media Entrepreneur Peter Bailey

This blog post is written by Peter Bailey. 

Like most men drawn to great endeavors, compelled to carve our names into history’s epitaph I’ve found my mother’s passions to be a great motivator. 


At 73 and more energetic than most of my millennial peers, Anita Bailey checks my tweets daily offering her “two cents” when needs be.


Alexander the Great’s relationship with his mother Olympias and her influence on his reign as then conqueror of the known world is a thing of legend. 


I’ve used the ancient leader’s ill-fated crusade through Asia as a cautionary tale applied to my own life of how we can be our own worst enemy. 


However, this mother son story began far from Macedonia on the island of St. Thomas where my mother settled to work as a maid after leaving Anguilla. She would eventually meet my father a fellow Trinidadian dreamer who turned her hopes of being a nurse into a reality. She was smitten with his brilliant mind, but I believe her Anguillian charm and beauty is what entrapped him. 

Anita Bailey

Peter’s mother, Anita, is from Anguilla.


Now stricken with Alzheimer’s he’s still alive because of her unwavering dedication and care. 


As a child I listened to her stories of growing up poor, walking barefoot to school and harvesting salt from the salt pond during the summer for coins, but she cherished it nonetheless always saying, “my hardships made me”. 


During my first and only visit to White Hill where she grew up my cousins stayed up into the wee hours retelling ghost stories. 


The one about the woman who put a spell on her cheating husband making him dance barefoot in a patch of cactus left me wide-eyed. We’re natural story-tellers in the Caribbean and some of the best ones were shared right there under the moonlight on White Hill. 


I savored the sugar cakes my great aunt Mildred Camilee Vanterpool-Hodge gave me on that trip, not knowing the soft-spoken lady was a national hero for her role in Anguilla’s Revolution and was laid to rest in a state funeral upon her death last year. 


She was married to my uncle John, himself a well-known local businessman. His sister Beatrice Stoddard, now deceased, was my grandmother. Her other brother Nathan Vanterpool was a laborer. 

Upon leaving to the University of Delaware my mother wrote Proverbs 22:29 on a napkin and stuck it in my wallet. 


“Seest thou a man diligent in his business? he shall stand before kings; he shall not stand before mean men”, has been my life’s mantra.


I took my mother’s spirit with me leading to an award-winning writing career at Time, Newsweek & Miami Herald only to become restless and at odds with a media climate not ready for my unconventional ideas.


Then hip hop legend Trick Daddy asked me to pen his life story leading to The New York Times calling the book “one of the pop music gems of 2010”, but the glory didn’t result in best-selling sales.


My vision of sitting on Oprah’s couch, making the rounds on prime-time as America’s new literary darling faded as quickly as it began. It’s every writer’s fantasy even if they’re too modest to admit.


I took a self-appointed exile of sorts from my lifelong adoration of prose, opting to create “NiteCap” my rebellion to mainstream media which would win me critical acclaim sharing some of the most provocative conversations with pop culture’s brightest stars that would air on NBC, BET, MTV and other outlets. 


I debuted the first episode on June 30, 2010 on my mother’s birthday. 


My publisher checked in with me over those years. Old colleagues wondered if I had “abandoned literary dreams for Tinseltown” after making my acting debut in an indie film alongside some Hollywood legends.


However, probing the minds of the likes of Mike Tyson, billionaire Don Peebles & 50 Cent couldn’t mute the incessant nagging of literary nostalgia. 


I began a grueling and humiliating comeback writing a weekly opinion column in Miami’s weekly black paper. Many would consider this a fall from grace, but true writers live to write, to use narrative nuance to express society’s collective fears, hopes and dreams.


We don’t care where the words are published. As a kid I scribbled down random thoughts wherever and on whatever I could. 


At my lowest point, where liquor became a destructive confidante, my mother told me: “Son don’t let anyone kill your dreams. Write your book. Sharing your story will set you free. You were born to write”.


I took her advice and began penning my memoir. Resentments and old wounds were dug up. At one point I cried, but my mother was right. It’s been therapeutic. 


It took me back to the Queens basement I lived in while writing for the Village Voice and the Brooklyn halfway house while at Newsday, evoked memories of the gangsters in Miami who embraced me when corporate society forgot about me, but most importantly it’s made me face my father’s terminal illness. 


Ironically, this process started after a break-up to which my mother, tired of my playboy lifestyle, tells me: 


“Find yourself a nice Caribbean girl who understands your culture. It’s high time you settle down. Cut out the nonsense and grow up”. 


In writing the pages of my life I’ve found myself. 


I’ve never felt so free and I’m looking forward to debuting a few chapters from my liberation at this year’s Anguilla Literary Festival with my mother and other Anguillian relatives in attendance. 


I can’t think of a better place to celebrate this literary homecoming. 

This blog post is written by Peter Bailey who will be appearing at the 2017 Anguilla Lit Fest.  For more information please visit


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