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Portrait Artist James Middleton Donates Gallery Proceeds To Jamaican Relief

Nov 15, 2025 | Arts & Culture, Business

By Andrew Macdonald

Bridgewater portrait artist James Middleton, who was born and grew up in Jamaica. has been a resident of Nova Scotia since 2012.

He now plans to donate all of his earnings from the sale of gallery paintings at Secord Gallery on Quinpool Road.

“I have been thinking about the terrible situation in Jamaica with the havoc from Hurricane Melissa. Many people have lost everything. It’s difficult for people in Canada to fully understand….the poor people have lost their homes, all their possessions, and have nowhere to turn. Heartbreaking,” he writes to The Macdonald Notebook.

“For the rest of the year, I will take 100 per cent of my portion of all of my paintings at Secord Gallery to go to a charity for Jamaican relief. I really hope this will help,” Middleton notes, although he admits it is a drop in the bucket.

“I have already sent a donation to the United Cajun Navy. I have been told they are reputable,” and he has already “sent them a nice chunk of change.”

“I was watching TV and saw the extreme poverty of people. Their shacks are all blown away, and their furniture is all soaking wet. They don’t have jobs. And I thought for the next two months to give up money from Secord – it’s not a big deal.”

I suggested to Middleton that it is a big deal, given that artists in general struggle financially, no matter their talent.

“True, good thing I have the portraits.” He has more than 20 pieces of artwork at Secord, and over the years “has sold quite a few.”

Middleton has painted some of the movers and shakers in the province’s business community, working with the Nova Scotia Business Hall of Fame’s annual event, and has drawn portraits of the late great John ‘Nova’ Chisholm, an Antigonish road builder, and also the late great nursing tycoon Brian MacLeod. He has also painted portraits of pollster Don Mills and his brother Jim Mills.

At Secord Gallery, he currently has artwork featuring iconic singers Joni Mitchell, Tom Petty and Mick Jagger. They retail for $2,900 and Secord Gallery keeps 45 per cent of the sales price, with the rest going to Middleton, so that is a significant donation to the Jamaica relief.

The Macdonald Notebook chatted with Middleton, who first moved in 2012 to LaHave with his spouse before going on to Bridgewater, where his artistic studio is located.

He has no relatives remainingh in the Caribbean country devastated by the hurricane. His siblings now live in Canada or the United States.

Middleton has been showing at Secord, which is owned by Phil & Wendy Secord, for a number of years. They took to the iconic singers that Middleton has painted because the gallery owners are also musicians. Phil plays bass in a part-time band. “They really like having those faces – legends and icons. I call them funky portraits.”

Middleton has also painted portraits of Keith Richards and Andy Warhol, as well as Queen, Freddie Mercury, and actor Clint Eastwood. Some of those paintings are now in private collections with some of Halifax’s top business leaders.

Middleton, now 69, grew up in Jamaica, went to high school there, and attended a year of art school on the island before going to Sheridan College at York University.

He is currently working on a commissioned portrait of Nova Scotia Supreme Court Chief Justice Michael Wood, which will hang in the courthouse on Upper Water St.

Some of Middleton’s portraits have previously been featured in The Macdonald Notebook, including one of Geoff Regan, which was displayed on Parliament Hill when Regan was Speaker of the House.

He also teaches landscape drawings, including taking participants of his class to Blue Rocks, a fishing village near Lunenburg. “People come from all kinds of different countries. The last class had participants from the U.S., Hawaii, Montreal and Australia. Those classes are advertised on his website, a link to the which is at the end of this article.

Middleton also teaches classes on life drawing, and those models come from the South Shore.

On his artistic website, Middleton talks about his approach to a portrait, including an initial meeting.

“Successful portraits are a true collaboration between client and artist. Prior to the start of the portrait, we discuss the details of the portrait, such as size (head and shoulders, 3/4 figure, etc.), mood, clothing and setting. We also discuss possible items to be included in the portrait that are especially meaningful to the subject, and where the portrait will hang,” he explains.

“We also discuss the ‘spirit’ of the portrait. The subject may want to be portrayed as dignified, important, or warm and approachable or perhaps a combination.”

Often, he works with a professional photographer who takes the client’s picture, and then Middleton draws and paints the subject from a photo.

On his website, he lists fees for the portraits, done in oil on canvas.

“I paint my subjects approximately life size, and fees are determined by how much of the body is to be included and the complexity of the background. Prices start at $5,000 for a simple head-and-shoulders oil portrait and can go as high as $50,000, or more, for a major institutional portrait. Multiple subjects will affect prices. I find that clients often have budget ranges and I always try my best to accommodate reasonable requests,” he states.

“No portrait is complete until both client and artist are completely happy. Nobody receives a portrait they are not thrilled with,” his guarantee states.

There is more on the process of painting a portrait on his website, as well as samples of his Nova Scotia and iconic legends’ artworks. The URL of his website: https://www.jamesmiddleton.ca/

 

Joni Mitchell, a portrait by Bridgewater’s James Middleton, is for sale at Secord Gallery for $2,900.  

Tom Petty portrait by James Middleton, on sale at Halifax’s Secord Gallery for $2,900.

 

James Middleton did this portrait of Antigonish road builder John ‘Nova’ Chisholm, who was inducted into the province’s Business Hall of Fame.  

A portrait of contractor Earle Casey, founder of Casey Concrete. Casey was inducted into the province’s Business Hall of Fame.  

James Middleton’s portraits have been recognized as award-winning. 

 

A portrait of business leader John Bragg, owner of Eastlink and Oxford Frozen Foods.  

 

Halifax business leader Mickey MacDonald’s portrait by Bridgewater resident James Middleton.  

James Middleton, right, with former House of Commons Speaker Geoff Regan. Middleton drew a portrait of Regan, that hangs in Parliament.  

Former Halifax West MP Geoff Regan helped to create his official portrait as a former House speaker. Regan created a beach scene, which is part of his official portrait as commissioned by South Shore portrait artist James Middleton. Contributed photo

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