“When mom says bedtime,
she means it. “
– Bolivar

Inspiration and author’s notes

BOLIVAR’S story began in a church basement.

In the early 1990s, my inspirational Sunday School teacher, Charlie, would often reference a character named “Bolivar Shagnasty” in his weekly lessons, inspired by the radio comedy “The Raleigh Cigarette Program,” by Red Skelton.

In his well-intentioned sermons, Charlie used Bolivar as an everyman; someone anyone could relate to… Whether it was sex, drugs or rock n’ roll, on Sundays, Bolivar learned a valuable life lesson.

Looking back, I sometimes question Charlie’s candor and transparency with a bunch of young, impressionable teenagers.

He often told personal stories in the guise of Bolivar; “smokin’ dope” while assembling vehicles at a General Motors factory, drunken debauchery or sexual encounters resulting in venereal disease… Don’t worry, Jesus, or Valtrex, was the answer to all these scenarios.

I loved Bolivar. His life was everything mine wasn’t, inspiring me to be… less than perfect, even if I was the “golden” child of my family. Around this same time, my family went from rags to riches after my father began practicing family medicine.

Whether it was teenage hormones, feelings of abandonment or imposter syndrome, Bolivar’s dark side began to resonate in my everyday life: logical, aloof, privileged and very much aware of the poverty I was eager to leave behind.

I began to use the character as my own dark alter-ego in high school cartoons. My version of Bolivar was dry, melancholy and sometimes stoned out of his mind, waxing poetic about the darker aspects of life, philosophy and bygone days fueled with drugs and sex.

Bolivar represented my deep and unfulfilled desire to become my own person; to escape conformity and the confines of my upbringing.

Bolivar cartoon shamelessly stealing a monologue from the character Buddy Cole of Kids in the Hall – circa 1996

Fun side note: I still order pizza using the name “Bolivar Shagnasty.”

Balancing life & death

More than 30 years later, Bolivar was a tricky character to write. As soon as I identified Maduta as the villain, I knew Bolivar was going to be her special son, and had an important role to play in the saga. And, just like me, her “golden” child needed to grow up, question everything and find his own path.

“How do you dissect, then rebuild your childhood on your own terms – accepting everything it was, yet knowing it might not have been what you needed? Carefully… and plenty of therapy sessions with a licensed psychologist.”

I found inspiration from the character Ricky Stratton, played by Ricky Schroder, in the early 1980s sitcom Silver Spoons. A young man adjusting to his privileged life with his newly-discovered father… As an aside, the episode with the Puerto Rican boy band Menudo lives rent-free in my mind.

Can the “Prince of Death” find meaning in life? Thrusting him in scenarios that would test his patience, logic and emotional intelligence felt like a compelling character arc. Especially when paired with Ghobli’s wisdom, Timmy’s cowardice and Kya’s strength.

Designing the Prince of Darkness

Concept art by Francesco Sala

In stark contrast to the character I designed in high school, as Maduta’s heir, Bolivar’s look needed to exude royalty, privilege and prestige, from his posture to his regal clothing.

As a character with such a rich thought life, his expressions needed to reveal glimpses of his inner monologue — the trappings of being the pampered “golden” child of a powerful goddess, kept secret from the world, yet longing to explore it.

My original Bolivar “headshot.”

Using Reddit, I found the amazing Cleber Junior, who helped expand upon my original “headshot” for Bolivar.

I think Cleber did a great job capturing the “royal” and studious aspects of his life. Yet, I needed Bolivar to be more nuanced in his expressions, and able to command attention without being overshadowed by his scene-stealing mother, Ghobli’s powerful magic or the unnerving Sebliss, master of potions.

Ultimately, I decided Francesco Sala could bring Bolivar to life, alongside Timmy, Kya, Tina and the others. Curious, privileged and with a lot going on between his ears… Francesco captured Bolivar’s energy perfectly!

Early concept art by Cleber Junior

Getting personal

At face value, Bolivar’s relationship with his mother, Maduta, is a funhouse mirror reflection of my own. As the youngest, and the “golden” child of the family, my mom lavished me with love, attention and affection. And, despite my protests, and being in my mid-40’s, she still refers to me as her “little baby boy.” Gah!

But, dig below the surface of the familial plot, and you’ll find Bolivar represents something deeper than a mother-son relationship.

For me, he embodies my polarities. A daily dance between my logic and emotions, strengths and weaknesses, confidence and fears, past and future, my bisexuality. Ultimately, who I am versus what I do.

Bolivar is my inner monologue, the dreamer within. He’s my intellectual horsepower, curiosity, quick wits and dark humor. He’s my tendency to deep dive into rabbit holes, my unending fascination with quantum theory, philosophy, religion, science and esoteric topics.

He’s the “magic” factor of my corporate presentations, my wizardry with a PowerPoint, my creativity and drive to make people wonder “how’d you do that?” A magician never reveals his secrets.

Bolivar’s story is deeply personal. He represents how I’m finding meaning in life, despite it sometimes feeling out of my own control.

I can’t wait for readers to discover, discuss and debate Bolivar’s mysterious backstory. From squalor to splendor, Bolivar’s life represents what many so many of us desire… but is it worth dying for?

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