An Interview with Theo Caldwell

Kaleem Hawa


Recently, TBAW staff has discovered an unpublished interview that was held by Old-Boy Kaleem Hawa in 2011 with Theo Caldwell. In anticipation of TBAW’s 7th anniversary on February 2nd and with Kaleem’s permission, we have decided to share the discussion today. In the interview, Kaleem talks fashion, the IB, and the environment with businessman and writer Theo Caldwell. 

Theo Caldwell

KH: Hi Mr. Caldwell.

TC: Hi Kaleem.

KH: I appreciate you coming in to do this interview with me.

TC: It’s my pleasure.

KH: So Mr. Caldwell, you graduated from UCC right?

TC: Yes, in 1991.

KH: And are any of the teachers that taught you still at the school?

TC: Yes. Don Kawasoe was my 6th grade Math teacher and Blair Sharpe was my Grade 11 English teacher. Oh…Mr. Miller was around then too, and everyone was still scared of him…

KH: And would you have described yourself as a strong student?

TC: Strong?

KH: Let me rephrase: what would you say your aptitudes and strengths were when you were at UCC?

TC: Oh, I think, when I was at UCC, it was always about joining as many clubs as possible and benefitting as much as I could from the various extracurricular programs that UCC had. I figure that it’s the same thing for you Kaleem. I was in so many clubs that by the end of IB 2, I had been awarded the Class of ’62 Trophy for extracurricular commitment.

KH: What were some of those activities you were involved in?

TC: Choir, Theatre, Football (though I was one of the worst players on the team) and, of course, Debating.

KH: You were the Head of the Club, were you not?

TC: Yes, and I carried my love of debating with me my entire life.

KH: And now, you are the McLeese Chair of Debating. Can you please explain to me what it is exactly that you do?

TC: Sure. It took me a long time to figure out what exactly the role required me to do, but the mandate is quite simple – to get students to debate.

KH: Oh and is part of that mandate inciting controversy?

TC: I prefer to say that part of my job is challenging the common conceptions that UCC students hold.

KH: I know that you’re trying to bait me into talking about the Global Warming Assembly, but I promise we’ll get to it.

TC: (Laughing) Okay.

KH: So, after graduating from UCC, what career path did you find yourself embarking on? Do you still do the same things?

TC: Well…I spent 16 years as an investment advisor, but now I mainly just go on T.V. and give financial updates. I was – and still am – a columnist for the National Post and Sun Media. I also became an author of 5 young-adult novels.

KH: And now you’re back at UCC.

TC: Right.

KH: And do you find that anything major has changed at the school?

TC: (Dismissively) Lots has changed, but probably the most evident change is the new system of education – the IB Program.

KH: You say that as if you’re not in favour of it.

TC: Actually, Kaleem, I’d say that I’m not. The IB Program has its problems. I think that after having it for so many years, maybe the school should attempt to reconsider it.

KH: And why would you say that?

TC: Well, our mutual friends in Debate Club have made it aware to me that it seems like the IB Program, which set out to facilitate easier acceptance into European schools, has actually made it more difficult

KH: And you’re sure that the IB Program is responsible for them not being able to get into the school of their choice?

TC: Well I mean, nowadays, you need to have 5 or 6 schools of choice, but yes. The way I see it is this: why have assignments marked overseas, when the faculty here know their students so much better?

KH: Well there you have to consider fairness. Teachers here realize early on which of their students are strong and which aren’t and, as a result, can have predetermined notions about that student’s quality of work. Marking overseas preserves the impartiality and the fairness of the marking.

TC: Yes Kaleem, but life isn’t fair.

KH: So wait. Are you saying that because UCC kids pay more to get into school, they should have a better chance of getting into university?

TC: (Firmly) No, no. That’s not what I said at all. I know how you do that sometimes. Let me be perfectly clear. Families who sacrifice so much to send their kids to this school –

KH: You mean monetarily?

TC: Well of course, in terms of tuition, but also the long commutes that some have to deal with. Anyways, I think that because they are sacrificing so much, their children deserve some sort of advantage.

KH: Isn’t this advantage present in the quality of teaching here at UCC?

TC: Why would you say that?

KH: I don’t know…I was under the impression that the quality of teaching here is better than in other schools.

TC: Well, I’m not going to comment on the teaching here, but all I’m going to say on the issue is that maybe the IB Program needs to be reconsidered. That’s all.

KH: And do you have the power to bring these problems to the administration’s attention? It seems like they’re very content with the IB Program.

TC: (Stoically) Unfortunately, this is true. But maybe it’s worth listening to another point of view.

KH: Okay, about viewpoints. Being a debater, I can safely say that one of our dominant characteristics is the belief that we are always right.

TC: (Chuckling) Well…

KH: We are also very politically minded. Were you like that?

TC: I really hope not. I think that 16 is way too young to have made up your mind about your politics and political opinion.

KH: So it was only later that you developed your political opinion. You mentioned being a writer for the National Post and the Toronto Sun…

TC: Yes, all the Sun Media newspapers. I have a column.

KH: The politics of those newspapers is very well known. Where would you say you got those values from? Did you adopt them from your parents or did you develop them on your own?

TC: That is an excellent question. I base my political beliefs on what I deem to have worked best. I am a free market guy. I’d love to support socialism and its high taxes, but in my opinion it just doesn’t work. Someone once said that Capitalism is the best of the worst. And I agree to some extent. Capitalism has it flaws, but no one that I know has ever been able to show me something that works better. In terms of my parents, I’d say that they weren’t political people and that even if they were, they wouldn’t have held the same opinions that I do.

KH: And do you think your time at UCC influenced your opinions in any way?

TC: Not at all. They acted against them if anything. You have to remember that we are living in Liberal Toronto – capital and lower-case “l”. I was in an academic institution with its own predominant mindset. Let’s just say that my opinions often made it feel like I was blowing against the wind.

KH: You were at UCC though. You make it seem like the school population didn’t agree with Capitalism. It doesn’t appear to me to be a minority opinion.

TC: Really? Well that wasn’t my experience. But let me give you a better example of something that I didn’t agree with which was present in overwhelming amounts when I was at school – recycling. When I was at UCC, the most important thing was being told to recycle. My parents began to worry about the opportunity cost of having to learn about recycling.

KH: Sorry, the opportunity cost?

TC: It’s an economics term. It means what you did instead of doing some thing else.

KH: Oh.

TC: Anyways, my parents started to think that I could be spending my time on something more useful than learning the benefits of recycling.

KH: But you didn’t have a course on it…

TC: No, but you know…I had my Geography teachers constantly preaching to me the importance of recycling. Environment this, environment that…

KH: Preaching you say… So would is it safe to assume that you felt indoctrinated?

TC: (Passionately) Definitely. All I wanted was a little open-mindedness.

KH: Sounds like the principle that we kept hearing when the Global Warming speaker came in.

TC: (Energetically) Kaleem, you wouldn’t believe it. It took me almost 5 months of lobbying to have that one 30 minute speech. 30 minutes of challenging the most cherished belief systems that the school holds – and yes, environmentalism is the school’s most cherished belief.

KH: So how did it all start?

TC: Every Old Ties issue that I received highlighted UCC’s successes in sustainability. I just thought that the students could be spending their time on something more useful. So I went to the administration and asked to have Dr. Ball come in. Normally, there is no problem. But the issue just snowballed.

KH: Yah, there were a lot of people who didn’t want him to come in, or at least wanted to see some other opinion be brought in alongside him.

TC: But you know what? I was empowered by the vote Dr. Power had in assembly. I think it showed that the student body wanted Dr. Ball to come in.

KH: Well you are forgetting the possibility of mob mentality.

TC: That’s true, but I think for the most part, people had no objections to him coming in.

KH: You also have to remember that Dr. Power phrased it as if a vote against Dr. Ball coming was tantamount to a vote against free speech.

TC: Kaleem, don’t be melodramatic – I was in the front row.

KH: Okay, assuming that the majority of students wanted Dr. Ball to come in, why didn’t he?

TC: He wasn’t in the city.

KH: So after Dr. Ball said he couldn’t come in, did you use your connections at the National Post to get Mr. Solomon to come in? He’s a columnist there too.

TC: Yes. I didn’t know him personally, but he offered to come in for free. That was a great gift to the College and something that I am personally indebted to him for.

TC: He represented a chance for people to be open-minded and to hear the other opinion.

KH: It appears that this was the main thrust behind the opening remarks you made in assembly.

TC: Yes, if you’ll remember, I wanted to be sure that the students’ belief in Global Warming wasn’t a result of that same indoctrination I encountered when I was at school. I didn’t care what their opinion was; all I cared about was the process they used to come to that conclusion.

KH: Except, if I remember correctly, you used a very different wording: you said that you didn’t care if someone rode their solar-powered unicycles to school everyday and that the only thing that mattered was that they heard both sides of the issue. Some people found the comment arrogant and offensive.

TC: Well I think that those people need to get a sense of humour.

KH: (Incredulously) What?

TC: No, I’m serious! It’s something that is severely lacking nowadays. But anyways, I think the assembly accomplished what it set out to do. I gauge this based on the number of people – including you – who came up to ask questions.

KH: Okay… Something that I, and many others had a problem with was that while Mr. Solomon claimed that the whole point of his speech was to be open-minded, he then turned around and went on to say how everything that we believed was wrong and that we were being brainwashed by our learning institutions.

TC: (Pausing). Yes, well, I think that part of argumentation is saying why the other side is wrong. Al Gore discredits the other side constantly.

KH: Yes but the burden lies on you both. Rather than drawing confidence from the other side’s misgivings, both of you, as advocates for open-mindedness, should accept some truth in the other’s opinion while also providing some reasoning of your own.

TC: I think that the whole point of our side’s argumentation is to prove why Al Gore and the environmentalists are wrong.

KH: Fair enough. One more question on this topic: would you say that Mr. Solomon’s speech was a success?

TC: (Indecisively) Yah, it was a success. Many questions were asked.

KH: You don’t seem too sure about that.

TC: Well, you see, I have spoken in front of many audiences, and there is none more difficult than UCC boys on a Monday morning. You need a talent to keep them engaged with your speech.

KH: So you think he was boring?

TC: I think he could have been more interesting.

KH: All right. Any new assemblies that you are planning for?

TC: Yes, I’m pretty sure there will be. Look forward to them. I’m going to continue challenging those conceptions that UCC boys hold so dear.

KH: One final question: how important would you say it is to be well dressed?

TC: Rather.

KH: And do you think you can tell something about someone from the way they dress?

TC: I’m not sure if you can tell something about their personality, but I think you can tell how much they want to be where they are. For example, if you’re having a meeting with someone and they show up in jeans and a T-Shirt, then it’s obvious that they don’t value being with you.

KH: So, does that mean I merit the three-piece suit, gold watch and the silk pocket chief that you’re wearing?

TC: Yes, Kaleem. You mean that much to me.

KH: Thanks for coming in.

TC: Thanks for having me.

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