Jerrine Kaiulani Jeffries

A personal history:

My name is Jerrine Kaiulani Madayag aka Jerrine Jeffries. I am a transgender female. My birth name was originally Clifford Alika Halemano, which I later changed to Jerrine Kaiulani Madayag in 1987.  I got my SRS (sexual reassignment surgery) in 2018.

Let me start from the beginning. I was born on May 1, 1953 to Mary Halemano and Isabelo Galima Madayag of Wahiawa, Oʻahu, who were not married.  My parents met each other at a dancehall in Chinatown sometime during the 1950’s. My mother was underage and was on the run from Girl’s Detention Home, which my father did not know. They left the dancehall and went to my dad’s place in Wahiawa, and my mom lived with him for a couple of weeks until the police came knocking on my dad’s door and took my mom back to the Girls Detention Home. And that’s where my mother gave birth to me.

Because of my mother’s situation, and that she and my father were not married, I was placed in a foster home two days after birth.  I lived in a very loving foster home from May 1953 till May 1960, with two very caring individuals, Antone and Flora Souza.  My foster father was a head foreman at Waipahu Sugar Mill and my foster mother was working as a babysitter.  At the time they also had their own children, who were already at an older age.  When I was sent to their home they also had been caring for two other foster children, Barabara and Chihuahua.  We grew up together like normal families.

As a child, I was already feeling like I knew I was different.  I would sit at the front living room window and watch my neighbor from up the road walk in front of our house and have this feeling of “uuuuuuu.”  As I got a little older, I remember being teased by my friends about me acting very “sissy” and “mahu.”  I would get embarrassed and cry a lot because of that.  But that still didn’t stop me from the way I was feeling. 

Living with my foster parent and foster siblings was a happy and fun time.  Those days, back in the 50’s & 60’s, were the best years of my life despite all the teasing and stuff.  Unfortunately, after I turned seven years old in 1960, the social worker notified my foster parents that she had found information about the whereabouts of my biological father, and that if I would be willing, that I should spend time with him to get used to my new family.

At the time I really had no choice, so I agreed, little beknown to me that my biological father had been seeing a divorced woman with six children living in a two-bedroom home in rural Waialua.  Life from that point on became very difficult, aside from me being a stepchild to a new family and being the way I was, feminine, soft, I was really feeling uncomfortable.  I didn’t quite get along with my new stepmother, who sent me to the hospital after hitting me on the head with a kitten heel shoe which left me with five stitches.  The doctor told us that, whatever happened, it was just centimeters away from my brain. 

I got along with my stepmother’s other children (sort of).  Her older son Lawrence was a little standoffish towards me, but later we got along.  She would constantly pick on me, make me do chores and anything and everything in the house, babysit my step brothers and sister, do the laundry, cook for my older stepsisters and family, and she would constantly abuse me verbally and tell my father, “Look he acting like one Mahu.”

So many times, I ran away from home and rode my bike to my foster parents in Waipahu. They would ask me why, and I would cry and explain. They would say, “they’re your new family now, so you have to listen to them.”  Then, they would call my father, and he would drive to Waipahu and pick me up.  I ran away from home a lot, which landed me in Juvenile Home at least twice a month. At one point I asked to stay with my second oldest stepsister.

Growing up in my teens and young adulthood was another hardship.  School was not for me.  I started to cut school as early as grade six.  I was sexually assaulted more than once.  I started cruising the park restrooms and bus station at an early age, 13 or 14. I think around age 17ish, I walked into the Glade Cocktail Show Lounge and was amazed at what I saw!! Showgirls in beautiful costume and big hair.

As I walked in the club, the bartender took a liking to me and asked if I wanted a drink, “of course I do,” was my answer, very butch and cocky. That was my first experience upon seeing my “dream.” I thought to myself, “that is what I want to be, A Showgirl.”  Shortly after that, I got arrested and sent to Juvenile Home again.  At around the same time, after I got out of juvey, age 17, I was sent to another foster home, which was ok for the time being.  It was through that foster home that I met up with my birth mother.  She tried to make up for the lost time, but it really didn’t work out.

During my short stay with the Celoza family, (foster parents #3), they had me volunteer for Army National Guard.  I was so excited at the time, but I couldn’t leave for basic training because I was still underage. At age 18, I was able to go to my basic training in South Carolina, where I went through my Advanced Individual Training and was then transferred back to Hawaiʻi to my National Guard unit, 442 Infantry Battalion located at Fort DeRussy, Waikiki.  Unfortunately, I missed one too many drills and was put on active duty and sent to Colorado Springs, Fort Carson.  I was stationed there for one year, then got orders to be sent to Germany. I finished my tour in 1-1/2 years, got an honorable discharge, and returned home to Hawaiʻi.

During my time in the military, I was more gay than gay and I became notorious and such a “slut” - lol. I had sex with everyone and anyone I could. It was easy, but also scary, being I was in the military. I had guys approach me more. At the time while I was in the military, I tried to commit suicide but couldn’t, but I remember thinking, I’m really messed up and what am I going to do with myself. I was starting to doubt myself. It was scary, but I stuck it out and continued my time in the service.  Fortunately, when I received an honorable discharge from the military, I got my bearings together and I tried playing the “straight” role by having a girlfriend. That didn’t work out, but till today, we are best friends.

By the time I got out of the military I was around 24 or 25 years old, and that’s when I was having more and more thoughts of being a woman. I revisited the Glades in early 1974 and started hanging out in the downtown area again, this time as an adult.

At this point in my life, I wasn’t quite sure what to do or what to expect. As time passed, I was getting to the point of “damn, this is a hard life,” living from house to house and trying to figure out if I was gay or wanted to become a transsexual.  Even being trans was hard, coming out to my family and physically showing up at the front door of our house in drag.  I was surprised that they accepted me right away. And that unexpected reaction made me confident enough to pursue being that person I’ve always dreamt of.

There was a time when I got into a relationship with someone which lasted for seven years, and I did get a temporary job with the state welfare office as a receptionist.  That lasted about six months or so after at which time we moved back to Wahiawa with my family.  It was back to the “streets,” which continued for the next couple years.  After that relationship, I got a job as a hostess at a Korean bar. Money was good for the time being, then I got tired and moved on to Chinatown with a friend. I started working as a server at Elsie Club Polynesian.  Ironically it was across the street from the Glade, where I also worked as a tape girl for a time.  But it was at Elsie Club, in 1989, when I won my first pageant, and from that day on my career took off and my glamorous life began.

I was invited by Empress Jovann Sarte to be a cast member of the Imperial Court of Hawaiʻi’s Ladies of the Diamond Cattleya (right), and my aspirations of being a showgirl and entertainer were set.

In 1997, I entered Golden Goddess (Mature, 40+) division of the Hawaiʻi Boa Arts Ball, and I won the title. I continued to pursue my dream and was asked to do guest appearances with various drag shows, including being a “Paperclip”in the cast of The Paperdoll Revue at Fusion Waikiki. That’s when my dream as a showgirl became a reality for me.

Ladies of the Cattleya, L to R, Valerie Keahiwong, Jerrine Kaiulani Jeffries, Libra Zamora, and catherine Lee Alphonse. Photo couresty of Jovann Sarte.

In 2000, I entered and won the title of Queen of Queens of the Hawaiʻi Boa Aarts Ball.

In 2006, Jeremy Lau and I were approached by Imperial Court of Hawaiʻi Queen Mother Charmaine Lee Anderson and King Father Bill Char and asked if we would consider becoming formal members.  After a couple of days of thinking it over we decided to go for it. And that’s when I realized what the court system does. At the time we were both Employees of Fusion Waikiki nightclub, and with the help of various venues and friends we were able to raise funds for various charitable organizations.

I became very passionate in what our mission and purpose was in the LGBTQI community. In order to keep up the momentum of this work, and to encourage and mentor the younger generation, I asked my two Crown Imperial Prince’s, Marshall Tokunaga and Harley Davidson, if they would join me.  They agreed, and in 2007 they became Emperor and Empress of the Imperial Court System Hawaiʻi.

In 2009, I became Empress, able to serve our community, loving every moment. By this time, I had introduced many of the younger generation to the important mission of the ICOH. Today, it is flourishing and serving our communities well.

Jerrine with Charmaine Lee Anderson

From 2006 to 2010, I was also involved with the Triple M Organization, Mr., Miss, and Ms. Gay Pride. I held the title of Miss Gay Pride Hawaʻi, another position I was proud and passionate about.

During this same time, I entered The Universal Showqueen Pageant (Vegas Showgirl Themed) and placed second runner-up, in 2006 and 2007.

I would like to thank the many friends who have helped me along the way with my goals and endeavors. Being a part of community groups and organizations taught me to be tough skinned and able to take punches, getting people to listen to what I had to say, and to receive advice that was offered.

I have met so many wonderful and very akamai (smart) individuals who have been an inspiration to me in so many ways.  And so many of these friends have made it possible for me to live my dream, showing me that anything is possible if I just put my mind to it. Believe in myself and I did. I hope to continue these long and loving relationships with each and every one of you and hope to see you all in the circuit soon.

Till we meet again, A Hui Ho, and Mahalo,

Jerrine Kaiulani Madayag, aka Jerrine Jeffries

Great Grand-Daughter to Empress Nicole The Great of All America

Recipient of The Double Eagle Award

Member of the Board of Directors of The Imperial Sovereign Court of Hawaiʻi

To my family who has been through this with me thru thick and thin, I love you for accepting and loving me for who I am. Thank you mom and dad for giving me life (in spite of all), and thank you to my lifetime partner David for putting up with me for 32yrs, (hopefully 32 more), I love you honey.

Images courtesy of Jerrine Kaiulani Jeffries, unless otherwise noted.