by Judie OronThe stage: Washington D.C., the White House, 1963. President John F. Kennedy is about to leave for Texas. In a dark hallway, he encounters President Abraham Lincoln. Each is convinced that the other is an apparition and what follows is a fascinating discussion between the two former national leaders. The above scenario is the setting for the two-act stage play, A More Perfect Union, one of several works written by Theo Caldwell and, like the man, the ideas are bold and, at times, downright fanciful.
Eminent businessmen aren’t usually spotted at Toronto’s stylish Spoke Club giving a reading of one of their plays, but, then again, most businessmen don’t possess the charm, humor, and intelligence of Canadian/American/Irishman (yes, he has three passports) Theo Caldwell. President of Caldwell Asset Management in New York, vice president of Caldwell Investment Management in Toronto, and a director of Caldwell Financial Ltd. in Toronto, his artistic and business personae are equally dominant. Writer, director, producer, actor – Caldwell wears all these hats, and more.
Caldwell, with his penchant for drama, seems to consistently speak in italics. And that’s only one of the many charming things about him. A tendency to blush is another, and woe to any female over age when that happens. Asked what it was like growing up with an IQ of 160, he explains that his older brother is much smarter but that he is the better dresser. He may be accomplished in many areas, but perhaps his greatest strength is his ability to be self-deprecating and deflect compliments.
Caldwell’s ancestors are equally colorful. A great-grandfather ran away from Bristol “in the middle of the night to get out of a wedding engagement.” His paternal grandfather came to Canada from the North of Ireland and started a sausage factory. Caldwell displays a photograph of his grandfather beside one of his trucks, pointing out the scripted capital C on the side of the vehicle, which Caldwell still uses in its logo today. His maternal grandfather, Fred A. Boylen, founded Urbana Corporation as a mining company. It is now an investment company which has recently celebrated its 60th year in business.
Caldwell grew up the younger of two boys in Toronto’s upscale Rosedale neighborhood. His parents - Thomas S. Caldwell, Chairman and founder of Caldwell Financial, and Dorothy Caldwell - met in high school and will soon celebrate their 42nd anniversary. “My father is the kind of guy that, if he’s teaching you to play chess when you’re 5 or 6, there’s no way he’ll let you win. I think, when he looks at me, he probably still sees that 5- or 6-year-old that he can stomp at chess,” Caldwell says, smiling. “My mother is an intensely private person, a woman of many skills.” Older brother, Brendan T.N. Caldwell, is president of both Caldwell Securities and Caldwell Investment Management, two companies that are among Canada’s top financial services firms. The brothers and their father “all have different skill sets,” Caldwell explains, but they work well together and share business and philanthropic philosophies.
The family recently did a very detailed DNA genealogy study. “It turns out that my dad’s mother’s X chromosome goes all the way back to that group of Europeans that today makes up 98% of all Jewish people in Europe and North America.” One family member, an officer in the Anglican Church the family attended in Theo’s youth, was a convert from Judaism, and the congregation studied Jewish culture and celebrated many Jewish holidays, including an annual Passover seder. Caldwell recalls his intense disappointment when Brendan was, for some reason, chosen to recite the tradition “four questions” although Theo was the youngest.
Caldwell attended Upper Canada College, and is still in touch with his former classmates whom he likens to “a sort of Diaspora of [brilliant young people] who later fanned out in Toronto and across the globe, doing many different things.” He did his B.A. in English at Trinity College, University of Toronto and his Master’s degree in Public Policy and Management at the University of London [England]. “I could see that I was going to be spouting off about policy and politics for the rest of my life,” he says wryly. “I figured that I ought to have at least one post-nominal degree so that if I was really stuck in a debate, I could whip out my degree and say, ‘Hey pal! I have a master’s degree in public policy.’”
In 2000, at the age of 27, Caldwell ran for Parliament in Canada. During the campaign, Eleanor Kaplan, [then-immigration minister for the Liberal government], “called all of us who were running for the Alliance [Party] bigots and Holocaust deniers. I said, ‘I would rather not use the Holocaust as a political tool and lose the election, than bring it up and win.’” He grins. “It turns out I didn’t use it as a political tool and I didn’t win the election.”
Caldwell ponders the fact that North American Jews don’t always vote for the people who are their staunchest supporters – i.e., conservative politicians. “I remember hearing from fellow conservatives, ‘Oh we’re going to swing the Jewish vote.’ But it didn’t move the needle an inch! At every election, I keep thinking, ‘This time the Jews will see who their friends are, they’ll see who is defending Israel’. But I haven’t seen it yet. I hope, some day, they will recognize how much we value the Jewish community and the State of Israel and reward us with their vote.”
When asked, in the light of his many acting and writing endeavors, whether he had planned to be a businessman in his youth, he answers: “I wanted to be a movie star. I wanted to be a writer. I wanted to be in politics. I wanted to do lots of different things. But I also wanted to do business – that was in the mix. And we had a bit of an advantage, obviously, it being a family business.” Caldwell tried his hand at acting, wrote plays and film scripts, directed and even had a pretty successful stint on Jeopardy. He shrugs, “I think my acting was like my hockey,” he says, smiling. “I worked really hard at it but I don’t know that the result was there.”
Caldwell’s plays, screenplays and his latest endeavor, a novel (the first of five parts – “anybody can write a trilogy,” he comments) about a legendary Irishman named Finn - may suggest the personality of a risk taker. “It took me more than a year to research my play on Tchaikovsky. My Kennedy-Lincoln play I really researched. Finn the half-Great was a profound amount of research over the last three years or so. King Arthur is only what he is because Geoffrey of Monmouth in the 12th century said, ‘Look, I’m going to take all these fables about this chieftain that existed 500 years ago and I’m going to make up my own story.’ And that’s why we know who King Arthur is. In the same spirit, I’m going to take all this stuff floating around – it offends me personally that people think Finn McCool is a bar – and I’m going to create something that is fun and enjoyable for people to read. And yeah, it’s a risk, because I’m not sure I’ll be able to go back to Ireland again! But I don’t care! It’s fun and it’s my hobby. While my dad is sailing or riding Harleys and my brother is planting trees, I’m writing.”
From afar, Caldwell may appear as somewhat of a dilettante, but that perception couldn't be further from the truth. When it comes to business, Caldwell is all focus, “You asked how many hats I wear. I wear, at the end of the day, one hat and that is looking after people’s money. That’s it. The rest is hobby. I had someone offer me a TV show recently, but I thought, ‘You know what? My clients don’t make a dime from me sitting around and making a television show.’ So I wear one hat but I do lots of different things. It’s easy to take a risk if it’s just your hobby,” he concedes.
About the family businesses, Caldwell says, “My old man started this company in 1980, with the idea of looking after high -net-worth people, of providing full service brokerage. And we’re still here, which is something, because my father has a list somewhere of all the firms that started when we did and I think there’s maybe two left. We are now largely an investment management firm, here and in the U.S. I am the person in charge of wealth management in the U.S., based in New York City - partially because I’m an American, partially because I used to work in that market before I came to the family firm. We also have Urbana Corporation, that’s sort of a closed-end vehicle, trading on the Toronto Stock Exchange. In the last few years, we’ve bought up stock exchanges: We have equity ownership in stock exchanges around the world. We were the second largest owner of the New York Stock Exchange before it went public. We made a good deal of money for people doing that,” he says. “We’re still the only people in this country, and possibly in the industry at all who buy exchanges for our clients. Even if the markets are plunging hundreds of points the volumes are still high because they take a piece of the trade. So it’s a little like going to a casino,” he says, smiling.
The idea of buying seats on stock exchanges around the world started with one seat on the Toronto Exchange, bought by Thomas Caldwell for $30,000 in 1980. In 2002, the seat was worth $50,000. “But then, when the Toronto Stock Exchange de-mutualized, that $30,000 investment became worth around $28 million [today] - that’s $50,000 to $28 million in about 5 years. So that was the ‘subtle’ way in which the idea crept into my father’s mind, that perhaps purchasing not-for-profit mutual type exchanges might be a good idea.”
As for where he sees the business in the future, Caldwell explains, “Obviously, I want to grow the business. I’d like to be a household name across this continent and throughout Europe and I think we’re doing the right things to make that happen. The way we get there is to maintain the philosophy that Dad has had from the beginning, which is that you get what you want if you help enough other people to get what they want. My brother has been gangbusters at helping other people get what they want – which is more money – with stock exchange investments. Whenever people come to us to do business, often the first question they ask is, ‘What’s your minimum?’ We always say to them, ‘We have no dollar threshold.’ What we do have is a personality requirement. We do business with people we like.”
Perhaps no cause is nearer to Caldwell’s heart than canine rescue. He’s dedicated his novel to Harvey, a purebred boxer, and even named his home Harvey Manor. “I don’t have human children,” he explains, pulling out a photo of a group of dogs on a lawn. In the photo, the dogs have custom metal contraptions built around them that Caldwell calls ‘wheelabouts.’ “Harvey developed what’s called degenerative myelopathy, where the back legs just stop working. He’s not in pain; he just can’t move his back legs. So, he can use his front legs and [his] dad’s got the caboose.”
The other dogs in the family have all been rescued by Caldwell from some nasty fate. Colby was blind when Caldwell found him at Boxer Rescue Ontario. After a recent operation, he can now see and lives quite joyfully, despite his 28 separate allergies. “I’ve made it clear to [Boxer Rescue Ontario] that whatever money is needed for whatever dogs they can get hold of, that’s the way it’s going to be,” he says.
Among Caldwell’s many philanthropic initiatives is a fundraising project for an integrated playground in Toronto called Neshama [soul in Hebrew], with accommodations for children with and without special needs. This subject has been close to Caldwell’s heart since his teenage years. “I went to a Christian camp in Muskoka called Pioneer Camp. It was then the only camp in Ontario with an integrated special needs program. I taught swimming to a group of kids who had Down’s syndrome and other disabilities. One guy would have a grand mal seizure every class and fall into the lake,” he recalls. “But he wanted to swim, so I said, ‘Okay, we’re going to have an inner tube right behind him and, when he has the seizure, we’ll be ready.’ It was a formative experience for me, to see the kids playing together. Just because a kid’s born with a disability doesn’t mean he can’t have as much fun as anybody else.”
Neshama’s budget is $1 million and the vision is that it will be designed to integrate play experiences for all children, including those with physical, cognitive, and developmental disabilities, as well as accommodating disabled parents. He hopes it will become a model for other similar playgrounds in the future. “I am gobsmacked that it does not already exist in Toronto,” Caldwell says, adding that they are planning a festive ceremony in spring 2008, with British royalty in attendance. The Caldwells are also large contributors to a hospital in Angola, and a Free the Children leadership center in India.
Caldwell remarks that the Neshama project began as a predominantly Jewish endeavor and is now a collaboration of the community at large. “[The Judeo-Christian] philosophies are the basis of Western society. So I hope that the common ground will continue to be recognized. I think the applications can be large, as in the future of the State of Israel and the Jewish people, or it can be small, as in the case of working together to achieve a small aim, in a neighborhood that we both share. We’re all part of the same community. I hope that they are as pleased to see me as I am to see them.”
