John Oswald and the education of a dealmaker

John Oswald nearly walked away from law school. He was doing well academically, but the abstraction left him cold. Business law changed that. It offered a connection between what happened in a classroom and what happened when people needed to finance, buy, sell or build something. Decades later, he was back at Brooklyn Law School, helping students find that connection sooner than he had.

In January 2025, Oswald described that early dissatisfaction to students beginning the school's Business Boot Camp. Here was a graduate from the class of 1984, now a Capital Trust executive and school trustee, explaining that being good at a subject and wanting to spend your life doing it were separate questions. For anyone privately wondering whether the profession fits, it is a useful admission to hear from the front of the room.

His involvement has been practical. He co-founded the program, contributes financial support and teaches. The course offers a compressed introduction to the language and decisions of business. Oswald's own career gives that ambition a particular weight: he has worked on the accounts, the legal arrangements and the investments. He has occupied several chairs around the same table.

An accountant enters the conversation

Oswald began his professional career as a certified public accountant at Arthur Andersen, specializing in real estate. He earned a J.D. from Brooklyn Law School and an LL.M. from New York University School of Law. At the international firm Lord, Day & Lord, his practice encompassed tax, real estate, mergers and acquisitions, and cross-border financing. These subjects would keep reappearing as his responsibilities expanded.

There is something satisfyingly concrete about that combination. A building may be bricks and glass to a passerby; to its accountant, lawyer and investor, it is also income, obligations, ownership and financing. Each discipline asks a different question of the same property. Oswald's early work put those questions in proximity. His later investment career kept them there.

Capital Trust's team biography describes him as an adviser to the group's U.S. private equity and real estate operations, a chief executive or board member of portfolio businesses, and a client representative in transactions. The work crosses the boundary between giving advice and accepting responsibility for a company. A beautifully drafted agreement, after all, still needs a business capable of living with it.

Today that biography identifies him as President and CEO of CTSA Holdings Ltd. and C.T. Capital International, Inc. Brooklyn Law School's trustee list uses President and Chief Executive Officer of Capital Trust Group. The titles sit within an international investment business, but the professional foundations remain recognizable: understand the numbers, understand the structure, understand the client's problem.

A client becomes a career

A tax assignment helped turn his work toward the Middle East. For a client facing a potential federal tax issue exceeding $70 million, Oswald secured a $7 million settlement. When he became a law-firm partner in 1991, he declined to announce the promotion, joking that he preferred his clients to assume he had held the rank already. The joke has an agreeable economy: why interrupt a favorable impression?

In the early 1990s, he moved to his client Capital Trust and helped establish its New York office. His advisory work included refinery privatizations in Sweden and Morocco and franchise negotiations in the Middle East and North Africa. The itinerary sounds varied because the underlying assignments were varied. Ownership changes, financing and expansion needed someone who could follow both the commercial plan and its legal consequences.

His SecuraCapital biography describes experience managing private equity funds in the U.S. and Europe, with mezzanine and equity investments ranging from $10 million to $100 million. The businesses involved had revenues ranging from $20 million to $1 billion. These are stated investment and company-size ranges, rather than a measure of his personal wealth or a promise about returns.

The same biography spans advisory assignments in energy, real estate, entertainment, education, construction, media and communications. That range supplies context for his classroom work. Students meeting him are encountering a career organized around transactions that cross industries. A client can change its product, country or ambitions; questions about capital and ownership come along for the journey.

A board seat is another kind of work

Oswald's career has also involved corporate governance. A 2010 regulatory filing recorded his service on the board of Kirkland's from 1996 to 2005 and his leadership of Verus International Group from late 2006 to 2009. It also described oversight of private equity investments, real estate holdings and public financing transactions. The record places him inside businesses as well as alongside clients.

In that filing, he was a director of the reporting company and chaired its audit, compensation and nominating committees. Those responsibilities cover the less cinematic side of finance: accounts, executive incentives and who gets a seat at the table. They belong in a career story because a transaction does not exhaust the demands of ownership. After the signing comes the governing.

A 2022 announcement about Fransmart identified him among its directors, alongside restaurant executive Joe Essa and strategic adviser David McClaskey. Oswald's investment-banking and office-and-retail property experience was part of the background he brought to the franchise-development company. It is another connection between finance and operating businesses, this time in an industry whose customers see the storefront before they ever think about its capital structure.

A pub with an unusually educational future

Business Boot Camp began in 2013 through a collaboration involving Oswald, Professor Michael Gerber, Deloitte's Barry Salzberg and Frederick Curry III, and Deloitte partner Anthony Campanelli. By 2023, its teaching device was a fictional business that grew from a family-owned pub into a public restaurant company interested in acquisitions. The pub had a busy future. Fortunately, its growing pains could be discussed without anyone losing a real lease.

Students followed decisions about business plans, budgets, financing, accounts and valuation. The course also addressed networking, client development and leadership. That combination makes sense for a lawyer: understanding a balance sheet is useful, and so is being able to ask its owner a question without turning the conversation into an examination.

During a 2023 conversation with Curry, Oswald suggested that graduates still deciding where they belong could explore different departments at a larger law or financial-services firm. His advice ended with a plain possibility: “you can figure out where you fit.” Coming from someone who found his own way through several professional disciplines, the suggestion has the benefit of lived sequence.

It leaves room for discovery. A student choosing a first job need not already possess a fully polished explanation of the next forty years. Oswald's advice gives exploration a place within the work itself. The first assignment can teach you something about your interests as well as your technical competence.

“you can figure out where you fit”

John Oswald · Business Boot Camp, 2023

The introductions are part of the curriculum

In January 2024, ninety students enrolled in the program's twelfth year. Its curriculum followed a hypothetical business from founding and initial capitalization through an initial public offering and the acquisition of another company. The week ended with personalized alumni breakout sessions and a larger reception. Students could put a person beside an unfamiliar job title.

Oswald also spoke with Curry about his career. Elsewhere in the program, students heard about entrepreneurship and the movement from legal training into business leadership. The format joined instruction to conversation. A financial statement can be explained in a lecture; the decision to change careers is often easier to understand when someone describes making it.

Oswald's alumni involvement extends beyond the classroom. In November 2018, he helped organize a Washington, D.C., reception at Poca Madre. He appears in the event photograph with Scott Stuart, Gerber and Hannah Cao. The following day brought a Supreme Court admissions ceremony for a group of graduates. Across these settings, the school remains a meeting place long after the diploma.

Showing up again

The 2025 Boot Camp placed Oswald on a practical legal-advice panel with alumni including David Barse, Asim Grabowski-Shaikh, Jennifer Horowitz, Stacy Kanter and Kenny Terrero. He and Curry also took part in a lunchtime conversation about their own paths. Both described working hard through college and law school, acquiring credentials and experience before building careers across law and business.

The detail matters because a career can look deceptively tidy once arranged beneath a title. Students heard about the work preceding the title. They also encountered different examples of where legal education could lead: investment, transactions, compliance and corporate leadership. Oswald's participation gave the program continuity while the surrounding experiences kept the conversation broad.

In December 2025, the school announced its fourteenth Boot Camp for January 5-8, 2026. Gerber and Oswald were named as its directors, working with Deloitte. The planned syllabus included financing, accounting, taxation, valuation, buying and selling businesses, digital assets and generative AI. Approximately seventy-five students were expected. The announcement also identified Oswald as President and CEO of Bridge Management East.

The recurring commitment is the meaningful number here. A program can be funded once; keeping it connected to practitioners requires repeated participation. Oswald's relationship with the course stretches from its beginning into preparations for its fourteenth edition. As new business questions enter the syllabus, its original purpose stays legible: help future lawyers understand what their clients are trying to accomplish.

Keeping the classroom door open

His work outside Capital Trust includes co-founding SecuraCapital Partners and AgriSecura Partners, serving as vice-chairman of both. He has also been a limited partner in Venture Philanthropy Partners, an organization supporting nonprofit institutions serving young people from low-income families in the National Capital Region. From 1990 to 1996, he chaired the New York-based Citikids Foundation, whose work included multiculturalism and environmental awareness.

These activities give his professional life another setting beyond a deal or a board meeting. The business-school exercise asks students to understand how an enterprise develops. The philanthropic work concerns organizations and opportunities in their own communities. In each case, money is accompanied by expertise, relationships or time. The form changes; participation remains tangible.

For Oswald, the return to Brooklyn brings the story back to an early question: what makes this education worth pursuing? Business law once supplied him with an answer. Boot Camp gives students a place to test their own. They can study a fictional company's next move, listen to a graduate describe an unexpected career turn, and ask how a decision works outside a textbook. It is a useful way to spend a winter break.