Eulogy By Hon Asot A Michael For Sir Rupert Willeston Valentine Philo

All photos by Antigua & Barbuda Festivals Commission

To his children, his family, love ones, friends, and fans in Antigua & Barbuda, Caribbean, and internationally I extend my deepest condolences for the loss of this cultural titan – Caribbean musical ambassador, a national and regional treasure, a respected and celebrated grandmaster of the calypso and soca art form – the legend Sir Rupert The Mighty Swallow Philo.

It was George Washington Carver (the great African-American educator, scientist, and inventor) who said, “When you do the common things in life in an uncommon way, you will command the attention of the world”. Sir Rupert not only achieved that, but he was also a trailblazer, fondly called the Mighty Swallow, King Swallow, De Birdy, De Garjo, High Flying, Soldier, The Cancer man, and to this day ‘King.’

From a humble beginning to a household name, at home and abroad; to international stardom, achieving world recognition and fame for himself; but more pleasing to him, for his twin-island nation. Apart from the ceremonial knighthood at home, the social benefits that should have been accorded him by the state to reflect the standard and quality of life he was deserving of, from the land he loved so dear, and gave his creative all, and represented in the acknowledged and phenomenal way, he never received.

He lived and died, the experience of societal ingratitude with the unkindest cut of hollow mockery for one who gave so much, to so many, and for so long, and so selflessly, and in the grandest of ways.

The mischievous may ask and so too the innocent inquirer: why is Asot Michael the one delivering the Eulogy? Is it because he is a parliamentarian or a former Minister of Government? No. For clarity and elucidation, Sir Rupert King Swallow Philo and his family and mine have been inextricably twined from time immemorial. His late sister Algeta grew up with my mother and father from the birth of my first sister Teresa-Anne in the early 1960’s and was part of our family for over thirty years.

It may be a forgotten fact. But one this moment requires revisiting to place me in the context of being here and to perform this sad and painful task to a loving and long life, lost friend.

I was one of a very select few privileged to listen to his unfinished and unmastered compositions. And when Sir Rupert King Swallow would land in Antigua with the finished first pressed LP 33 or 45 from Charlies Studio New York, his very first stop would be the Patrick A Michael Department Store on High Street, where the monster speaker boxes were outside on the sidewalk in front the store and the turntable at the ready to blare out Swallow’s new release. DJ Patrick would send the sweet music, lyrics, rhythm, melodies, and tempo blaring and blasting in deafening decibels. And the dancing crowds would gather, emptying the Golden Peanut and Brother B’s restaurants. I remember the frantic phone calls from Ivor Bird. Swallow has a red hot, new release and big, bad ZDK radio does not have a copy. So my late father would ensure that ZDK had the new hit to be aired the same day. Yes, Patrick Michael Store on High Street was where King Swallow Philo songs would be first released before the radio stations.

When his loud cry pierced the midnight hour to announce his arrival on planet earth on Valentine’s Day in 1942, the midwife immediately proclaimed “this bouncing baby is going to be a singer”.

And what a singer he turned out to be! King Swallow… Sir Rupert Willeston Valentine Philo… One of the most loved composers and performers of calypso the world has ever known. Seventy-eight years later, the good and faithful servant has been called home to rest. As loving and humble as he was born in the trash house by the St Bartholomew Church in Willikies, richer in the quality of his life than any millionaire, more loved than any big-time celebrity and more respected than any politician.

A few days after his birth, his grandmother Mathilda went to Mr. Michael in town and ask if he had any cot cause her grandson born and sleeping space was tight. When she got the cot, the other siblings couldn’t touch it, or it would be 6 lashes each, so the other siblings just stand by and watch their brother. Sir Rupert Philo was christened and confirmed at the St. Stephens Anglican Church.

As a child he attended the St. Baths school and helped on the farm tending to the animals especially his donkey Dandy Ball that he was particularly fond of. His childhood companions were Oneil Joseph, Robin Yearwood, Cordell Daniel, Bentlet Cornelius, Edmund Cornelius, the late Jerome, and Dr. Prince Ramsey; he attended the Goodwill Academy and made friends with James Tanny Rose, Clarance Crump, MP Cutie Benjamin, and many more.

After leaving school he taught at the Goodwill Academy (Henry School); with the help of Mr. Bird, he learnt the trade of carpentry at Mill Reef Club; he served in the Antigua and Barbuda Defense Force; he went back to the books and passed his Cambridge exams with flying colours; he worked in the airline industry; He spoke Spanish and French; He was a Sunday School teacher and acolyte at the St Stephens Anglican Church.

Sir Rupert Philo met his love of 55 years at the AYPA meeting at St. Batholomew in Willikies. They produced two (2) children Shennette and Derry Philo, he would always travel abroad, but nevertheless would always return home to Lornette (Edith). They had their ups and down, ins and outs, but the relationship was always there. She would also travel with him abroad or just to accompany him on his shows. Nothing was too good for his Edith and the kids. In fact, his song ‘Loraine’ was dedicated to her. After he wrote it, he told her ’this one is for you’. When he took sick, she visited him at his home in Gambles he told her he wanted to come home. Her reply was ‘you are home’. Then he replied “home with you. I’m not staying here all the days of my life”. And so he went home and was cared for by his daughters and Lornette (Edith) Thomas, who was by his side until he passed.

The father of seven – Wayne, Shennette, Randy, Derry, Kevin, Renee and Dwight – Sir Rupert was 5th of eleven children and the 1st of four boys, born to Zachariah and Maudestina Philo. He loved siblings, he laid down his life for children and he adored his grandchildren. He was the little prince to his sisters – Hildred Thomas Carlos, Rosa Philo Baltimore, Eugenie Philo Coates, Algeta Philo, Sybila Philo Henry, Valerie Philo Barton and Hillarine Philo. He was the proud, protective big brother to Glenor Philo, Vernon Philo, Shelly Philo and Terrance Philo.

Sir Rupert was a kind, gentle soul who grew up shining the light of love through the changing scenes of life and giving a helping hand to family, relatives, neighbours, friends and people in need. He rode the tensions of success and failure, thirsty for truth, in fear of God and strengthened in the conviction that the flame of his little candle would always be powerful enough to dispel the darkness of evil and negativity. A wonderful husband, father, grandfather, brother and friend. We give thanks and praise for the blessing of his life… for the bright soul that rejoiced in musical creations to bring us joy, peace and perspective.

His musical journey began with singing in Church and at school concerts and learning to play the keyboard. Then one day Sir Rupert’s long-time school friend Jerome Ramsey, whose sister Amy paid him his first 25 cents to sing a calypso, said to him that he could make money like the Mighty Sparrow, because he was always singing the songs of the Calypso Maestro. “A sparrow is a bird”, Ramsey said, “and there is also a bird called Swallow”.

The both laughed. Unknown to them at the time, they had just initiated a giant of the calypso artform with the stage name Swallow.

He worked at LIAT for at least 2 years, from 1974 to 1976. Swallow then decided to turn his love of music into a full-time career. Terminated from one job, and with a choice between the airline industry and carpentry, Swallow picked up the microphone and entered his “Soca Kingdom,” convinced that he could survive in the entertainment arena.

Teenager Swallow entered the calypso competing ring in 1961 and immediately gave birth to the political calypso in this country with a song about Dominican Republic dictator Raphael Trujillo and his oppressive treatment of migrant workers from Antigua and Barbuda. He slammed Trujillo as ‘a wicked man’ who forced migrant workers ‘to put every cent’ in the tyrant’s hand, before they could leave the land’.

A four-time calypso king, Swallow first took the crown in 1973 with “March for Freedom” and “Push Yah Push Dey”. He won again in 1977 with “One Hope, One Love, One Destiny” and repeated in 1978 with “Dawn of a New Day” – one of the greatest social commentaries in Antigua and Barbuda calypso. After six years seeing the monarchy land the hands of his rivals, King Swallow roared back to the top spot for the final time 1985 with “Town Mash Down”.

Through the years, his competitive nature coupled with the unwavering support of the followers from the east, forged a legendary rivalry with the other two internationally recognized champions of Antigua and Barbuda calypso – King Short Shirt and King Obstinate. Their titanic contests fuelled his growth, sharpened his competitive edge, drew some of the largest crowds at Carnival City for any calypso competition of the day or subsequently. Without a doubt that rivalry was not only responsible for establishing the highest standards of calypso competitions in the region but for making Antigua’s Carnival one of the most sought-after global Carnival events and one of the greatest summer festivals anywhere.

Swallow credits those moments as some of the most satisfying and inspiring of his career.  But he created an even greater legacy in conjunction with his calypso colleagues and sponsors by hosting Antigua’s oldest and most consistent calypso and cultural entertainment institution – Swallow’s Calypso Pepperpot, the University of Calypso and Soca. It was the greatest calypso institution ever in the history of Antigua & Barbuda which was the incubator and nursery for calypso and calypsonians.

Swallow’s genius as a composer and performer of classic calypso party music won Five Road March titles and made him the first calypsonian to grace the stage at Radio City Music Hall in New York. Dubbed the king of the annual Labour Day Street Jam in Brooklyn, the pride and joy of Willikies is still the reigning Caribbean Calypso King.

The impact of his irresistible soca and calypso music was arguably bigger abroad than it was at home. Indeed, several Trinidad and Tobago soca stars, grateful for the value of his contribution in the Mecca of the artform have paid glowing tribute to the GARJO, a real boss in the Soca Kingdom.

He was a complete calypso and soca artist, more complete than most. A great writer and melody maker, a commanding and imposing stage presence, a master at delivering and commanding crowd response. In competitions, he was spellbinding with his social commentary, and it was almost a certainty that Sir Rupert King Swallow’s sartorial elegance was going to be pleasingly imposing; his was a visually striking, impactful, and captivating attire. What a compelling fusion of artist sartorial elegance, command of the stage, a master of delivering his songs, the party rocker, the one who always ignites the spirit of the dance hall with his sweet melodies and jumpy rhythms, while on the road his music is sure to mash down tung.

He was a great creative and imaginative lyricist, a dynamic composer who was able, almost always to fuse his creative lyrics with an almost incomparable consistently sweet and captivating melody. Making the people “want to wine on something,” and “whole night in the fete,” or on the way to or from the fete “in the back seat.” Having penned the lyrics for all his songs, Swallow lent his composition skills to the Department of Culture and the Carnival Committee. This musical pioneer has made promotions through music his mission. Swallow’s inspiration has always been fueled by his love for calypso, Carnival, and ultimately Antigua and Barbuda.

He received a knighthood – the Grand Cross of Princely Heritage – along with the Order of Merit in Antigua and Barbuda. His long record of recognition also includes numerous accolades from Trinidad and Tobago, Grenada and the US where he received an award from Senate Majority Leader Dean G. Skelos and a most prestigious induction into the Sunshine Awards Hall of Fame.

As much there was “Fire in the Backseat” of the “Subway Jam” with “Satan Coming Down” and fans screaming “Don’t stop the Party”, the use of a super power’s launch of a satellite in space to fill the galaxy with witty lyrics, haunting melody and compelling rhythm, lives with us as arguably his finest work:

“Uncle Sam send up some men on a space mission

In this crew was Sally Wright the first space woman

The mission was to plant some satellite up in space

So the challenger take off from Canaveral in a haste

But before the mission could be accomplished…

The whole of orbit like now is foreign music

The astronaut and them was feeling to party

So they turn the mission in a space party…

Everybody happy, jumping up and down in the party

Wailing up their body everyone enjoying the party

Fire! Fire! Fire! The galaxy is on fire!


Sir Rupert fell ill in August of 2017 just about the time when he usually travelled to New York for Labour Day.  He would usually call his children to let them know he had arrived in New York and was safe.  After realizing he didn’t call, his eldest daughter took it upon herself to call, after calls went unanswered she got worried and then decided to call Mr. Rawlston “Charlie” Charles his manager who advised her to get to New York. She gave up her job to be at her dad’s side. After Sir Rupert was released, it was months of being back and forth for follow-ups, both dad and daughter hitting the streets heading to Kings County Hospital. Swallow was known all around, even the nurses from around the Caribbean knew who he was as they came to his room with cell phones playing his songs on You Tube.


As the days went by and he started looking gloomy, he would remind his children to look to God and always pray. In his own words, “don’t be afraid to call on God, talk to him like you talk to me, ask for what you want, God is there for you. The girls would get a good scolding but for the boys he always wanted to know if they were alright because he “doesn’t have the time with WhatsApp, ‘lol’, and Facebook. He loved all his children, but would always mention his handbag, Shennette.


In his last week in the hospital, he would always cry when his daughters arrived and mentioned about going home. He never wanted them to leave or leave without him. He would hold his daughter’s hands and told them how much he loved them and to tell their mom how much he loved her and he’s coming home soon and to be safe on the road.


In his final days, as the exemplary musical astronaut prepared for lift off to the heavenly space, he reminded his children of their upbringing as Christians of good conscience focused on the priorities of Mathew 25 – help your brother, help your sister, help your neighbour. Food for the hungry, water for the thirsty, shelter for the stranger, care for the sick, clothes for the needy, comfort for the heavy burdened…


“For I was hungry and you gave me something to eat, I was thirsty and you gave me something to drink, I was a stranger and you invited me in,

I needed clothes and you clothed me, I was sick and you looked after me, I was in prison and you came to visit me.’


“Then the righteous will answer him, `Lord, when did we see you hungry and feed you, or thirsty and give you something to drink?

When did we see you a stranger and invite you in, or needing clothes and clothe you? When did we see you sick or in prison and go to visit you?’


“The King will reply, `I tell you the truth, whatever you did for one of the least of these brothers of mine, you did for me.’


He urged his children to live God’s word, look to Him and keep praying. In his own words “don’t be afraid to call on God; talk to Him like you talk to me; ask for what you want; God is there for you.


Sir Rupert Willeston Valentine Philo, an exemplary family man, was born to greatness. He was blessed with the talent of music and the capacity for love and human kindness. There were times when he questioned why man to man is so unjust and struggled with difficulties over who to trust. Indeed, there were times when the injustice for this rock-solid supporter of the Antigua and Barbuda Labour Party was brutal even from his own comrades of Labour Party while we blindfolded ourselves in the sound of silence

We were there singing along with Swallow “V.C. 50 Years at the Wheel” and “If You Can’t Run The Country: Give It To Labour Party” We were there when Swallow voted for the Labour Party in every election until he could vote no more. We were there when Swallow religiously joined Labour Party pickets and marches against the George Walter and Baldwin Spencer administrations.

But, were you there, when political victimization by those he criticized brought him to his knees? Were you there when the broken promises from the party he steadfastly supported deprived him of just compensation for government’s acquisition of the property on which an entertainment centre on East Street and Independence avenue was built from his sweat and toil?

Were you there, when this quintessential national treasure was being shamed and served up one humiliation after another in his unending efforts to gain partnership rights to Woodberry Park property on Old Parham road as he sought to establish a public entertainment and cultural (Pepperpot) Centre?

Where you there, when he refused the offer his dear friend Winston “Gypsy” Peters’ offer, who was then Trinidad and Tobago’s Minister of Arts and Culture, to have the Trinidad & Tobago government sponsor and hosting his 50th anniversary celebrations because he felt this historic event was for the people of Antigua and Barbuda?

Were you there, when because of that patriotic and nationalistic love and commitment to his nation and his people, he personally bore a great deal of those expenses for that event, which left him in debts up to his neck, allowing for mean-spiritedness, envy, and jealousy to take its course in prosecution accompanied by the greatest humiliation of his life – that this national treasure, this Caribbean Cultural Icon and Ambassador, was ordered to be held in a public cell in St. John’s City?

Were you there, as he wept, as his heart bled, as his pride was imprisoned with accused and hardened criminals?

Were you there, when the State should have assumed the full cost and expenses for hosting his 50th Career Anniversary celebrations so that he would not have had any responsibility for goods or services?

We owe him so much, not only for the international publicity he gave to this nation but also for the joy, happiness, entertainment, economic and financial benefits that his life work bestowed on Antigua and Barbuda.

Today, as our nation and the Calypso world stand in honour of the life and times of Sir Rupert “King Swallow” Philo, let us do now what we did not do for this great national icon and Caribbean Cultural Ambassador’s priceless contributions to this nation when he was alive. In honour of his memory, let us agree to settle all outstanding debts owed to him by government so that his children can derive the benefit of his legacy that he did not receive, but should have. Let us also agree to the erection of a life size statue of Sir Rupert at the entrance of Willikies Village.

Go in peace and righteousness, my friend, my Bro, Sir Rupert King Swallow Philo, a classical and grandmaster exponent of the Calypso and Soca art forms, a most distinguished national, regional, and international cultural ambassador you were. You gave the best of yourself for the enjoyment of all of us. We are all eternally grateful to you. May you find your place and peace in glory land.

Somewhere up there in the melodious voice of a King we hear the words:

“Come, you who are blessed by my Father; take your inheritance, the kingdom prepared for you since the creation of the world”.

May flight of angels sing him to the eternal party in space in the heavens above.

May his soul rest in peace

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  1. I greatly appreciate the sentiments given at Swallow’s funeral, but I need to add that Swallow was a labour party supporter and supported many fights against the UPP and the PLM. Now in any good conscience have these political never done any good for Antigua? I would have liked to read a more unbiased account of anyone’s life without any impingement in political commentaries. It was under the UPP that Swallow got his knighthood, and the UPP gave him an entertainment job at Ffryes during labor day when many Labour Party supporters tried to persuade him not to go. His reply was,” ah work me ah work.” He took the job and was paid like all other singers. The UPP has never been partisan when it come to The Antiguan and UPP always looks after the Antiguan first. Swallow is an Antiguan and an important man in all our lives. UPP gives honour unto whom honour is due. It never corrupted the country in anyway, but it tried to run a clean government full of justice and fair play.

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