By the time you read this, Jack Matthews will have won. The Dallas City Council will have chosen him, after reviewing the proposals of the five other developers vying for the opportunity, to build its much-debated convention center hotel. He will be sitting down with his design partner, London-based Foster + Partners, to decide exactly how he’ll change the city’s skyline and, to hear hotel boosters tell it, rebuild the city’s economic engine and revitalize downtown and bridge the racial divide between North and South Dallas.

Or not. This story was written in late April, a month before the Council was scheduled to vote on the matter. So maybe Matthews didn’t/won’t win. He’s certainly the underdog developer. Say the Council went with Beck or Woodbine Development or any of the other bigger developers with their plans on the table. Pick one. It doesn’t matter. Jack Matthews still wins.

If another firm gets the nod, Matthews will still own a prime, developable parcel of land just south of the Convention Center. And he’ll still own an even bigger chunk of property a short walk away—more than 1 million square feet on and around Lamar Street, from Interstate 30 to his signature project, the South Side on Lamar loft complex. He had already planned to develop the entire thing, long before the hotel was a reality; the Convention Center deal only speeds up that process. He’ll do just fine, thank you.

So how did a Canadian expat come to Dallas and wind up saving our city? It wasn’t by accident, and he didn’t come out of nowhere. Prevailing in the convention center hotel skirmish is merely Matthews’ most public victory. The 50-year-old developer has been buying land in the Cedars area since the late 1990s. 

But to answer the question more succinctly: it’s probably because he wears khakis.

When picturing a big-time developer, you might conjure the image of a man in an immaculately tailored suit topped off by an expensive haircut, a sharp wheeler and dealer who moves through life like a shark—never sleeping, always hunting. Or maybe you think of a different sort of alpha male, a boots-on-the-ground wildcatter, the kind of plainspoken cowboy with dirt beneath his fingernails and permanent hard-hat hair, Jock Ewing reanimated and armed with a fistful of tax abatements.

Jack Matthews fits neither of those archetypes. He dresses like the manager of a Best Buy. He breaks out a suit for groundbreaking ceremonies and the occasional meeting, but it mostly stays in the closet in favor of khakis and dress shirts. His hair is wispy and gray. His physique leans toward doughy. He looks, well, he looks soft—like the sucker at a card game.   

And that’s just it. No one sees him coming, this shark that looks like chum. No one expects the genial Canadian with the soft voice to be behind the biggest office tower under construction in North America. But Matthews is. The Bow—a 58-story, curvilinear skyscraper in Calgary—is set to open in 2011. In person, Matthews doesn’t look like that guy. At best, he looks like the guy who reports to that guy.

So if you’re wondering how Jack Matthews came to Texas and made a pile of money off land no one else really wanted, maybe that’s how. When he made that first big bet in 1997, buying the old Sears, Roebuck & Co. catalog center and saying he planned to turn it into lofts, maybe everyone looked at him and just saw another poor schlub blowing his cookie-jar money. Maybe that’s how he was able to amass more than 30 acres of vacant lots and neglected warehouses fortuitously positioned between the potentially revitalized Convention Center and the Trinity River.

How else to explain—when every new real estate project in the city is met with squinty-eyed skepticism from the community—that Matthews has yet to wake up on the wrong side of a Jim Schutze column? His plans for Lamar Street keep moving along while he hides in plain sight.

That camouflage extends well beyond Matthews’ wardrobe. His casual-Friday, just-folks appearance permeates his entire company, Matthews Southwest, a small operation headquartered in Lewisville. The place is as mom-and-pop as a major development concern can get. About 40 people work for Matthews, with 10 doing business out of the main office. He says they like to refer to it as “a small company that does large deals.”

It’s been that way ever since Matthews and his wife, Laura, and their four children moved from Mississauga, Ontario, in 1994. Shannon, 22, graduates from St. Edwards University in June; John, 20, is in his third year at SMU; Samantha, 18, and Tori, 16, are still in high school. The kids are all more or less Texans.

“The kids were very young when we moved, and I think that made it easier,” Matthews says. “We had some adjusting, but it has been great fun the last 14 years in Texas. In Toronto, you put the garbage in the trash, and here you put the trash in the garbage. People also like to hear me say ‘out’ and ‘about.’ It is somehow funny.”

It is, because the way he says it, it’s “oot” and “aboot.” His accent is like a pair of khakis for his voice, another part of his makeup that helps him sandbag the competition. You never think to get “oot” of his way.