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Over the past 25 years, he’s worked closely with Don Cherry and several past and current NHL stars, designed World Series cover art for the Toronto Sun, worked for the Toronto Blue Jays and most recently, was commissioned to produce this piece for the Greater Toronto Hockey League’s All-Century Team.

Later this fall, MacDougall will be launching a line of T-shirts in conjunction with the 40th anniversary of the Toronto Maple Leafs’ last Stanley Cup win.

We recently caught up with MacDougall over the phone at his Oakville studio.

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sportsnet.ca: How did the Mets project come to you?

MacDougall: I was contacted by Paul Cartwright. He’s someone I’ve worked with on a few projects in the past. He initially came to me to design his logo for his sports celebrity company. He was pretty familiar with all the sports art I’ve been doing in the Toronto area. I’d spent quite a few years doing paintings in and of baseball.

For the Jays I was their so-called “official artist,” so when they had a special commemoration I was commissioned.

And this went all the way to the early ‘90s when the Blue Jays were winning the World Series.

sportsnet.ca: How involved were you with the Mets day-to-day? Did they just leave you with the assignment? Did they give you a photo to work off? Did you talk to Mookie and Buckner?

MacDougall: I actually had no conversations with them at all. A lot of images were forwarded to me that Major League Baseball allowed me to use. There were certain parameters that I had to adhere to. I had to make sure that the World Series logo was used in some part.

The play itself? I basically got carte blanche on that.

In my situation you have to be a designer as well as an illustrator. You have to figure out sizes and shapes and decide what’s going to work. If you look at that painting, I decided to make the play the centre of the attraction so when you look into that painting, it’s there, but it’s offset by the portraits of Mookie Wilson and Bill Buckner.

I always found that it was kind of odd that Bill Buckner would want to sort of glorify a moment that wasn’t such a highlight of his life. It’d be like me getting a phone call from (Vladislav) Tretiak saying he wanted to commission me to do a painting of (Paul) Henderson’s goal in the ’72 Summit Series on him and he was going to go on a circuit and sign all of these autographs.

At some point in time I guess they just have to come to terms with the fact that, “hey, you know what? I was part of history. It was a big screw up, but you know what? I think I can make a few bucks off of this.”

That’s how I’m seeing it.

sportsnet.ca: Were you watching the game back in ’86?

MacDougall:: Oh yeah, I was watching that game, for sure. (Ray) Knight was on second, there were two out and Mookie hit that ball through Buckner’s legs and it was done.

I immediately thought of The Curse, how Boston just couldn’t get the break. They had the championship and they lost it. It’s the Curse of the Bambino, I thought.

sportsnet.ca: Your Toronto Sun cover art during the Blue Jays World Series years were pretty popular. Whose idea was that?

MacDougall: Working in the newspaper business you never know what’s going to get thrown at you at every day.

In this case, my sports editor was Mike Simpson and he said, “Listen, we’ve got an opportunity to do a cover wraparound. Are you interested?”

My next question was always, “How much time have I got?”

And they usually come back with, “No time.”

I never turned down a job because if you start turning down jobs, you lose your job.

Paul Godfrey was the president of the Toronto Sun at the time and he was a big fan of my work. He purchased the originals of both wraparounds from me. So when he went from the Sun and eventually ended up with the Blue Jays, I started getting work doing paintings for Robbie Alomar, Paul Beeston, Dave Winfield, Clemens, Tom Cheek even.

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TORONTO SUN COVERS: World Series '92 | World Series '93

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sportsnet.ca:Tell me about your relationship with Don Cherry?

MacDougall: It began in 1985 when I graduated from art school. I wound up working for his television show in Hamilton, Don Cherry’s Grapevine. I wound up doing all of the caricatures of the guests on the show. Every time they went to a commercial, they zoomed in on the caricatures.

Then I designed his Don Cherry’s restaurant logo, a bunch of T-shirts for him and about five Rock ‘Em Sock ‘Em covers.

It was one of those cool experiences that I didn’t really realize how cool it was until you get a chance to sit back. We did many projects sitting at his kitchen table while (his late wife) Rose would be looking after my kids in their basement.

I learned a lot about Don Cherry. People really don’t have any idea of the type of things he does behind the scenes for kids and for people that are in the hospital. He does so much.

I just really learned to appreciate all the things that he’s doing. A lot of people don’t care for him, but if they actually saw the good things that he does, I think they’d change their minds.

sportsnet.ca: What’s been your strangest assignment?

MacDougall: I’ve had some crazy assignments, but some fun ones too. I did a painting for Geddy Lee from Rush for Alex Lifeson’s 40th birthday years ago. That was fun to meet them. Big baseball and hockey fans as well.

sportsnet.ca: Are there any projects, or dream assignments you’d like to take on? Maybe someone that you haven’t worked with yet, but would like to?

MacDougall: I used to do paintings for the Conn Smythe celebrity dinner in Toronto. This one year I had contacted Muhammad Ali in Kentucky and worked out a deal to do a painting of him fighting (George) Chuvalo as a commemorative from 1966 when they fought in Toronto.

I thought it would be a great painting. I got the agreement from Chuvalo and Ali to sign 100 prints for the dinner, but unfortunately George Chuvalo’s son had passed away and within a week George’s wife had decided she didn’t want to live anymore.

So after that happened, that deal was gone. I’ve always thought about resurrecting that again, but who knows?

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Below: MacDougall takes you inside his studio as he prepares a special project:

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