Building Cities, Bridging Borders: John E. Drew on Where Real Estate Meets Global Trade
In this episode of The Matthews Podcast, host Matthew Wallace sits down with a true pioneer of public-private urban development—John E. Drew, Founder and Chairman of The Drew Company. From shaping Boston’s iconic Seaport District to advising U.S. trade policy and guiding the World Trade Centers Association (WTCA), Drew’s multidimensional career has made an indelible impact on real estate, infrastructure, and international commerce.
From Government Service to Real Estate Visionary
Unlike many in real estate who enter through family legacy or private sector apprenticeship, John E. Drew’s journey began in government. Serving under the Mayor of Boston and the Governor of Massachusetts, Drew was tasked with repurposing surplus federal properties—decommissioned military bases and naval yards—across Massachusetts.
“I came in through government,” Drew explains. “I worked with the mayor, then the governor, leading commissions to figure out what to do with these massive, suddenly unclaimed properties. It wasn’t just redevelopment—it was about retraining people, restoring economies, and rethinking what community means.”
Navigating the complexities of military site closures, Drew helped orchestrate community engagement, stakeholder buy-in, and feasibility analysis, all of which became cornerstones of his development philosophy.
Building Consensus Amid Uncertainty
Real estate, for Drew, is as much about diplomacy as it is about blueprints. “People didn’t want the military bases to close,” he says. “So the first challenge was emotional—getting through that denial and showing people a path forward.”
His approach was rooted in realism: organize structured community feedback, work with government departments to retrain affected workers, and bring developers into public forums to introduce “reality into the discussion.”
“You can’t do everything. There’s not an endless supply of money. You have to make tradeoffs based on actual market demand.”
The Birth of The Drew Company
After leading some of the state’s most transformative projects, Drew founded The Drew Company. Drawing on his public experience and knowledge of government incentives, he began executing private developments, including Constitution Plaza and the Bayside Exposition Center.
“Once I made those connections and gained that experience, the next step was clear. I was ready to go out on my own—sometimes still in partnership with those I worked with in government—but always with the aim of doing more.”
Seaport: A Case Study in Urban Placemaking
Perhaps Drew’s most defining contribution to Boston is the Seaport District. In partnership with Fidelity and the Massachusetts Port Authority, The Drew Company transformed industrial port land into over 2 million square feet of premier mixed-use space—including the Seaport Hotel, World Trade Center Boston, and Seaport East and West office complexes.
“It was a public-private partnership. The Port Authority kept ownership, we developed on leased land—which presented financing challenges. But it worked.”
The vision was comprehensive: walkable waterfronts, transit access, mixed housing, cultural venues, retail, and office space. “We even selected the kind of trees we’d plant,” Drew chuckles. “Urban design at its finest.”
And while the location was initially met with skepticism—“People thought it was too far from downtown”—Drew’s team literally mapped out distances to prove the area’s walkability. Eventually, the market followed, and today, the Seaport is one of Boston’s most vibrant districts.
Crafting Mixed-Use Success
How do you decide what to build in a blank-slate neighborhood? Drew emphasized market analysis and sequencing. “We didn’t force it. Housing came first. Then retail followed. We added grocery stores, restaurants, and eventually luxury retail.”
As foot traffic grew, so did tenant demand. “We ended up with a retail ecosystem that rivaled Newbury Street—completely unexpected when we started.”
Global Expansion Through the World Trade Centers Association
Beyond Boston, Drew has also made waves on the international stage. As Chairman of the WTCA and Chairman of Trade Center Management Associates, he’s overseen projects in Washington, D.C., Dublin, and advised countless others globally.
“The WTCA is about facilitating trade—not logistics, but human connections. We offer exhibition halls, office space, and—most importantly—knowledge. That makes our real estate more than just buildings.”
The Boston World Trade Center drew companies like IBM and international newspapers. “We used our meeting space to attract regional trade groups. That filled our office tower faster than any broker could have.”
Navigating Global Trade Turbulence
On the topic of globalization, Drew remains optimistic—but realistic. “Trade’s been around since the Greeks. It’s not going anywhere. But we are seeing diversification. Companies are looking beyond China to Southeast Asia and Latin America.”
He warns that political volatility and shifting tariffs create uncertainty. “Businesspeople just want rules. Tell us the rules, and we’ll figure it out.”
Advice for the Next Generation
Drew’s advice to aspiring real estate professionals is clear: master finance, find mentors, and understand market fundamentals. “The more you know about private equity, debt structures, and spreadsheets—the better decisions you’ll make.”
And on a broader note, he encourages U.S. firms to consider global expansion. “We have immense knowledge here—from lease tracking to property management—that’s rare in developing markets. There’s real opportunity abroad for those willing to explore it safely.”
Looking Ahead
As chairman of the WTCA for the next two years, Drew hopes to compile and promote a global portfolio of emerging World Trade Center developments. “We’re in strong markets, and there’s phenomenal real estate abroad worth investing in.”
John Drew’s career is a masterclass in bridging government and private enterprise, local needs and global opportunity. Through vision, empathy, and technical expertise, he’s not only transformed neighborhoods—he’s helped reimagine what real estate can mean in a connected world.
