Inseparable: The Late Gregory Isaacs And His Wife, June

When Gregory Isaacs and his wife, June, were arrested for illegal possession of firearms in 1983, the Cool Ruler‘s young wife remembers being scared. Very scared.

“I remember a lot about that arrest. It still stands out….we were badly beaten …two firearms oh my God…young girl…had no idea. They found 2 firearms in our house. We were in jail for awhile at the HWT lock up…no bail….then Gregory took the rap. He pled guilty. I was freed and he paid a fine,” she told DancehallMag.

At the time, Isaacs had just released his commercially successful Night Nurse album. Even though his incarceration meant that he was initially unable to promote the album, Night Nurse hit No. 32 on the UK Albums Chart in September 1983 and was certified Silver in the country, almost 40 years later.

That jail stint was just one of his many infractions over the years. The troubled singer was also arrested repeatedly for possession of cocaine and struggled with addiction for many years. However, it is the love story between Isaacs and a quiet teacher, June, which is part of his endearing legacy.

June and Isaacs tied the knot on December 1, 1983.

By all indications, it was a whirlwind romance. At that time, she had just graduated from the Shortwood Teachers’ College at the age of 24. She was swept off her feet by the debonair Cool Ruler, a snappy dresser.

“Gregory was very classy. He loved fine suits. Most of the suits he wore were bought in designer stores in London. He loved getting dressed. He would tell me , “mummy step out like a millionaire …even if you’re going to the market’….I still do that up to this day…,” she said, laughing.

Isaacs was a bit of a dandy, topping off his suits with fine hats. Fans will remember his cameo in the 1978 film “Rockers” where he wore a powder-blue tuxedo and black fedora.

“He was always dapper, he had hats and suits like no one. I still have some. My favorite is seeing him in full suit of white with his hat leaned to one side smiling with a little of his gold teeth showing,” she reminisced.

However, unlike the movies, it wasn’t love at first sight.

“I met this man while shopping downtown Kingston one Saturday. It was in Randy’s Records. I was a student of Shortwood Teachers College.
Our eyes made direct contact for a little while and so he came over.
He came so close that I become uncomfortable,” she said.

June was a bit flustered by Gregory’s attention.

“He was whispering in my ears and I didn’t like it….worst he was a rastaman….no way was I entertaining him. I couldn’t wait to get out of the shop and it seemed like he couldn’t wait for me to get out too,” Mrs. Isaacs said.

Despite her initial discomfort, Gregory turned on the charm.

“I was uncomfortable. He was persistent. I watched him keenly. He wasn’t the typical Rasta….He was clean as a whistle…his locks barely visible …and his cologne could tell he had good taste He was nine years my senior and that was worrying…he treated me like a child. He was on campus every day. He was one sweet caring intelligent guy that I couldn’t wait to see at visiting time,” she reminisced.

Before she knew what was happening, Mrs. Isaacs had fallen in love with the phlegmatic reggae music icon whose aching vocals, stage swagger and obsession with true nature of love, loss and heartbreak had made him a hero to global music fans. And her life would never be the same again. She had found a love that only the poets of old seemed to write about: enduring, all-encompassing and dangerous.

“He was on campus every day. He was one sweet caring intelligent guy that I couldn’t wait for visiting time,” she said. “I loved everything about him.”

Eventually, they became – as she put it – ‘an item’.

It was that endearing love story for the ages that inspired Mrs. Isaacs to host an annual concert dubbed ‘Red Rose For Gregory’ which was held annually on Valentine’s Day. This year, the concert will be held on Mother’s Day at Hope Gardens in Kingston on May 14.

“Red Rose was shifted to Mother’s Day this year after getting information that there was going to be a massive show headlined by Shaggy with international acts on my same day culminating with the music conference held here. So with Gregory having a song, ‘Thank You Mama “, I quickly shifted to host this year’s concert on Mother’s day using that song as my theme,” she explained.

The show will be headlined by the Manhattans, and will feature performances by Deniece Williams, Etana, JC Lodge, Robert Minott and Errol Dunkley.

She’s unsure if she will return to the traditional Valentine’s Day date.

“I will see how it goes as the ‘lovers’ look forward to a prestigious concert during Valentines and it also enhances our involvement in Reggae and Black History month,” she said.

Isaacs is known for hit songs including Feeling Sad Tonight, Love is Overdue, Mr Brown, Night Nurse and All I Have Is Love.

June and Isaacs separated seven years before his death in October 2010 at age 59, from lung cancer. Though separated, they remained married.

He made his recording debut in 1968, but came to fame in the mid-1970s with a string of hits in Jamaica. In the wake of Bob Marley & The Wailers’ commercial breakthrough, he soon became one of the leading live reggae acts internationally.

Known as the “Cool Ruler,” Isaacs recorded numerous albums – some sources say 500 – for a wide range of Jamaican and U.K. labels. He was once signed to Virgin Records subsidiary Front Line Records, for whom he recorded 1979’s “Cool Ruler”. He released 1980’s “Lonely Lover” and 1981’s “More Gregory” for Pre Records, a short-loved subsidiary of the UK label, Charisma Records.

His Night Nurse album, was recorded at Marley’s Tuff Gong studio and released in the United Kingdom by Island Records. The album’s title track was later famously covered by Sly and Robbie and Simply Red and went to No. 13 in the U.K. singles chart in 1997.

Another of his most enduring albums was Red Rose for Gregory, an 11-track album released in 1988 by RAS Records. It combined the style and sound of lover’s rock with roots reggae and featured the hit, Rumours which peaked at 98 on the UK Singles chart.

In 2016, he was posthumously awarded the Order of Distinction (Officer Class) in recognition of his contribution to Jamaican music.