Cracked Hat: The non-sports fan behind the James portrait — and a few dozen others

In early 2013, I was looking for an illustrator to draw a portrait of Bob Dylan for the Minneapolis Star Tribune’s annual Minnesota Profile. At the time, I had a limited experience with the market, so I reached out to Los Angeles Times AME Michael Whitley and sought his advice.

I asked for a list of people to consider. Whitley responded, “Robert Carter.” I said, “OK. Who else should be on my list?” His response was, “He is your list.”

Whitley is someone I trust, so I took the list and ran with it. The portrait was a resounding success, and I became a fan. Over the next year and a half, I worked with Robert Carter twice more. First, in sketching Adrian Peterson for the Star Tribune’s 2013 NFL preview, and again this past week on a breaking news illustration for the Cleveland Plain Dealer when LeBron James announced he was returning to the Cavaliers. You can read my account of that process here. As with that recounting, this is not about me.

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Carter is an Ontario-based illustrator whose canvas portraits have peppered the North American media landscape for the better part of the last 10 years. If you’re short on time, you can cut directly to his work at

Even a cursory scan through his portfolio will reveal: Stephen Strasburg for the Washington Post, James for the Plain Dealer, a breaking news conceptual illustration for the Star Tribune off of the Super Bowl announcement this spring, and just about anything you can imagine for the Los Angeles Times (from months-long planned Oscars preview illustrations to same-day breaking news portraits of Magic Johnson and Dwight Howard). Some of the figures he has drawn include: Barack Obama, Mitt Romney, Tiger Woods, Joe Paterno, Michael Jordan, Jon Stewart OK OMG YOU GET THE IDEA.

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Derek Simmons has been managing editor/visuals for the Minneapolis Star Tribune since December. Prior to that, he was deputy design director at the Los Angeles Times from 2007-13. In his role, Whitley credits him with introducing Carter’s work to the Times and helping make it a quasi-staple in the paper.

Since moving to the Star Tribune, Simmons and news presentation editor Josh Penrod have already used Carter for a pair of high-profile illustrations. The first was the aforementioned Super Bowl illustration, which was done on a single deadline.


The second was the paper’s Major League Baseball All-Star Game preview, which ran Sunday.

[stands up.]

[points toward lead-buryin’ hut.]



[goes to lead-buryin’ hut.]

The Plain Dealer’s James illustration ran on Saturday. The Star Tribune’s cover ran the next day. Carter turned both of those illustrations around on concurrent deadlines, meeting vastly different needs in the process. W. Even. T. F?

Whether you’re a fan of his work or otherwise, you can surely agree that’s some impressive time management, organization and demonstrated ability to work with multiple art directors.

For this post, I asked Whitley and Simmons about their history with Carter. And I asked Carter to break down the insanity that was his week on concurrent freelance deadlines.

This is a long-form post, so it’s going to be long. Enjoy

• • •


Michael Whitley, AME, Los Angeles Times: Robert Carter is one of a handful of illustrators we try to work with several times a year. The design of the LAT can be pretty minimalist with very spare use of color and Robert’s style feels like an natural extension of that. His work is right at home on our pages and he understands us in the way a staff illustrator might — what we are going for and what we are trying to accomplish. He is also just really great to work with, and you know you are going to get a result.

It is funny how often we have asked him to work with us on sports specials. He is not a big sports fan, but it is part of the reason I like working with him. He asks smart questions and he wants to get all the little details right. He also challenges any assumptions about what the reading masses will and won’t understand. Anything too insider will not make sense to him, but that means it will leave out a lot of readers, too. I like to think we also bring him some challenging things — imagined scenes that never really existed for example — and sometimes on crazy deadline. I like to believe the Magic Johnson and Dwight Howard pieces really opened illustration up as a breaking news tool in U.S. papers.

He has also done a lot of really smart work for other areas of the LAT. He did President Obama and Mitt Romney for A1 pieces on each candidate, a great take on sliding down the broken economy for Business and an Oscars preview that hangs on the wall at the LAT to this day.

Ultimately the reason we have a 6-year relationship with him that continues is because the quality of his work is extremely high.


(On the topic of using Carter’s portaits for breaking news visuals.)

My first choice for breaking news will always be something live from the scene, something new, something quality. But sometimes you can only get two of those three. What if there is no press conference? What if the principals don’t make an appearance at all? When there is nothing live, is something new and quality possible? That is where I think the value of a breaking illustration is.

When a group including Magic Johnson bought the Dodgers, we were facing a sports cover with a file photo of Magic. So not even a photo really related to the Dodgers sale in any way. And it needed to cary an entire cover. We kicked around ideas revolving around Magic, the very successful business man. That lead us to the idea of a portrait of Magic in a suit with the Dodgers cap on.

Robert was, for us, the only choice to pull this off. We imagined it in his finish with the Dodger blue really coming forward. I think he thinks we are crazy, but he was up for the challenge when Derek called with the breaking illo idea. Not every artist would have been. It was a risk for him as well.

I’m not sure he could have done better with a week to do it instead of a day, except it might have been more relaxing for him and us. … In the end, we got something new and something quality that pushed the story forward.

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Derek Simmons, managing editor/visuals, Minneapolis Star Tribune: I came across Robert Carter’s work in 2008. At that time his client list didn’t include any American newspapers, but I remember being taken aback by his penchant for portraiture. The level of detail in the likenesses was stunning, but at the same time there was a calming simplicity about his work. In particular, I was drawn to the spot color pieces with those beautiful backgrounds of grays and blues. Standing apart in a crowded field of portrait artists isn’t easy.

Being different in that genre often means being bizarre or sacrificing the quality of the likeness for the sake of being different. Not so with Rob. His paintings are unmistakably his yet maintain an unwavering level of commitment to the subject. You never look at his work and think about the style first and the person second. It is always the other way around, and that’s a huge tribute to his talent. The first project we worked on together was a baseball preview for the Los Angeles Times in 2008. It featured two dreadlocked players with similar roles: Manny Ramirez for the Dodgers and Vladimir Guerrero for the Angels. Rob hit it out of the park.

We’ve worked together 15 times during the last six years, most of those illustrations appearing as special section covers for the LAT, but a few here at the Minneapolis Star Tribune. I go back to him time and again not just because of his incredible talent, but because he’s fantastic to work with. He attacks an assignment with the same intensity whether it’s your idea or his. And he is incredibly fast. We once asked him to paint Magic Johnson in an L.A. Dodgers hat for use in the next day’s paper. Rob was out running some errands when I reached him, but he drove back to the studio and had the final illustration to us in about six hours. Quite amazing.

• • •

Robert Carter (On Robert Carter)

There is something I need to confess… I am not a sports fanatic. There it is, I’ve said it. Phew, it’s nice to get that off my chest. I sometimes felt like a sham. I’d think, “If they ever found out I know jack-diddly about sports, I’ll be mocked and wedgied to tears. I pray that’s not the case and hope this declaration will not hinder my career in sports illustration, because I am a big fan of that!

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(On the Star Tribune’s All-Star Game Preview)

It was a busy week. I’d been asked by Derek Simmons to illustrate a full spread for the Star Tribune to celebrate the return of the MLB All-Star game to Minneapolis’ Target field. Josh Penrod took the lead on art direction and communication as Derek was just leaving for vacation, (although he would be checking in here and there.) It was a big project with a lot of requirements.

There were two ideas for the concept, both included the stadium and cityscape as the backdrop and a depiction of all-star players from past and present (’2014 ’85 & ’65) The first concept was to show them playing on the field together. However it would be difficult to pull off that kind of scene and still maintain portraits of distinct players. So I felt the second approach would work better, which was to depict the players lined up along the dugout fence.

Derek had said “Technically there is no dugout fence but…” and gave me permission to take artistic liberties. Going this route was beneficial in that, although their backs are turned, the viewer will know by their jersey exactly who they are. Plus it makes for a great scene having all these legends (living and dead) lined up side-by-side enjoying a ball game together. I was given a wish list of players they’d like to see, names like Kofax, Carew, Clemente, Stargell, Killebrew, Mays, Aaron, Gibson, Valenzuela, Rose, Gwynn, Brett, Ripken, Gooden, Trout, Puig, Cabrera, Beltran. For the most part I had no idea who these guys were or what they looked like. So I narrowed it down to nine of the top picks and started to get to work!

There was a lot of research I needed to do first. I had to find out who these guys were, who they played for at the time and gather as much reference photos of them, Target field and the Minneapolis cityscape as I could. There was a lot going on here, but I wanted to keep it as simple as I could, not only so it was instantly readable but also to cut down on my work load, allowing me enough time to get it all done. Part of that decision was to block the actual field from view. I thought it was superfluous with everything else going on and it saved me from painting a field full of tiny major leaguers.

After submitting the rough I got some feedback. Derek and Josh are very collaborative, understanding and supportive, so this process, — which can sometimes be a grind — has never been difficult. There were some concerns about wanting to show some of the players faces (the original rough you could not see Rose, or Gwynn’s face) a change of the arrangement of a couple players and other small tweaks (all of which made sense) otherwise it was good to go! So I sat down in earnest and got to painting!

A few days later I finally got it done the night before it was due. Happy with what I’d done, I was proud to email it off and get some well-deserved z’s…

“Morning Robert, People LOOOVE the illustration” Sweet! … “but there’s a problem.” Fak! “We’ve heard from longtime Twins followers and fans here in the newsroom… That’s not Killebrew.”

In my research, I’d found some photos of Harmon Killebrew but never anything decent with his back to the viewer (which was the case for many of the older players) So I just had to do my best.

“The common consensus here: People remember him most as a guy with even less neck and more rounded, slightly beefier shoulders. Almost a guy with “sloppy” hunched-over posture. “

So with that suggestion, at the eleventh hour I made an adjustment to the Hall-of-Famer’s posture, removed the billboard signage and sent what was to be the final printed version. I hope the diehard fans approve.

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(On the Plain Dealer’s LeBron James cover)

Just as I was putting the final touches on the Tribune piece I got a message from Crutchmer in Cleveland (who, coincidentally, I first worked with while he was at the Star Tribune, and it was Derek who suggested me to him.)

“Dude, What is your week like? We are getting some ducks in a row in anticipation of LeBron James re-signing with the Cleveland Cavaliers…”

Crutch said they’d need it in a day or so as the announcement would be soon. Working with Josh has always been a pleasure, and — don’t tell anyone — to be honest, I actually like doing rush jobs. There’s no time for second-guessing yourself or over-rendering, you just have to dive in and do it! Which can be stressful but also exhilarating. Needless to say, I said I’m in!

By the time they came to me, Crutchmer and (Plain Dealer AME) David Kordalski had a pretty clear vision of what they wanted. Black & White, front-on portrait of Lebron, arms raised in his ritual chalk toss before games, wearing a Cleveland Caveliers #6 jersey and two championship rings. I suggested we make the type on his jersey gold and we were off and running.

I wanted the image to be simple, dramatic and eye catching. There are many photos of Lebron basically in the pose I needed for reference, so that wasn’t an issue. But they also wanted to see his face, so I couldn’t tilt his head back too far, as it is in many of those photos. I found several reference shots I liked and using different aspects from those various pics I sketched out my rough line work and sent it off to Josh and David. Thankfully they approved, as time was of the essence!

Because this would be breaking news, and the actual day and time Lebron was to make the announcement (assuming he was even coming back to Cleveland) was not known, it had to be ready as soon as possible. Crutch “Try and have it at a point by 10 tonight that if he does announce it’s the Cavs, we can call it good and run with it.”

Eek! Well that put my feet to the fire.

Generally, I do try and move around an illustration never spending too much time on one thing but work it all up somewhat gradually. But, in this case I was very cognizant of the fact that I had to keep the whole thing moving so that in the 3 hours or so I had, it had to be at a point they could use if necessary.

LeBron - wip

Thankfully, the announcement wasn’t made that night and I had the next day to finish it the best I could. I submitted the final and everyone seemed to really like what I’d done.

Robert Carter

Lebron did announce he was coming back to Cleveland (nice!) And the page was a big hit! (extra nice!) I’m proud to have been asked and trusted enough to contribute to the project.

• • •


(And once more, Carter on Carter)

My first real sports related illustration came via Simmons at The Los Angeles Times in 2008. He commissioned a portrait of the dreadlocked Manny Ramirez and Vladimir Guerrero. I remember telling it to my brothers Matt and Steve, both of whom are giant sport fans, and have always been there since to offer counsel when needed on any of my sports related illustrations. I guess Derek liked the portrait well enough because we’ve continued working together to this day.

It was through those projects that lead me to work with other fantastic people, and for major publications, giving me the opportunity to paint the portraits of some of the most famous athletes in the world — LeBron James, Adrian Peterson, Michael Jordan, Stephen Strasburg, Chris Paul, Dwight Howard, Tiger Woods, and Magic Johnson — which is always thrilling and stressful.

These guys have a lot of devoted fans, I don’t want to bum them out by sullying their heroes’ visage, let alone piss off the athletes themselves. It’s a privilege and I take it seriously.

I’m blessed to get to do what I do.

• • •

Crutchmer here: tl;dr Your loss. Just go to and gawk, then.

About Josh Crutchmer

is design and graphics editor at The Plain Dealer.

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