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Craig Steven O’Dear, The Story of an Athlete Becoming a High Profile Lawyer

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Being a lawyer is difficult. It is a huge responsibility since their arguments can determine the fate of large amounts of money, and who goes to jail or goes free. It requires dedication, hard work, and endless hours. Few have achieved the highest ranks of the profession, but Craig Steven O’Dear is among those few who have done so.

An American lawyer, Craig Steven O’Dear, is a corporate litigator and legal advisor who has managed to establish himself as one of the finest corporate trial lawyers in the country. Due to his passion and hard work, he has been consistently recognized for his efforts in The Best Lawyers in America, Chambers USA, Missouri & Kansas Super Lawyers since 2006.

STORY OF AN ATHLETE

Born on June 26, 1957, in Northeast Missouri, Craig S. O’Dear is the son of H.C. O’Dear and Martha Lou O’Dear. His father was a farmer while his mother was a school teacher. He spent his childhood on a hog farm south of Lewistown, where he completed his high school education. 

Craig was an accomplished athlete in high school. He was a prominent basketball player and track athlete and played quarterback on the first-ever Highland High School football team. His parents were very proud and kept records of his athletic years. His father drove him to play basketball with the  Quincy  Herald-Whig publisher’s kids on a  YMCA  team, beginning in the fourth grade, every Saturday.

When Craig was a student, the school only offered a basketball program, and there was no football program. Craig’s father was a member of the school board. He, along with other local leaders, decided to start a football program. Coach Pat Wozniak was hired as the first football coach.

Coach Wozniak formed the first football team of the school comprising the school’s star basketball players and farm boys who had never played organized sports. Wozniak led the team to a 9-0 record in their first year, acknowledging the efforts of the young and confident athlete, Craig O’Dear. The coach said, “Without the quarterback, that wouldn’t have been possible to have that record. That was a big, strong, smart kid.” He graduated from Highland High School in Ewing, Missouri.

Craig’s success in football, basketball, and track in high school landed him a football scholarship at the Missouri University of Science and Technology. O’Dear played football and ran track at the university while pursuing an engineering education. He graduated with an engineering degree in 1979.

Apart from having a stellar background in sports, his father paid for Craig’s flight lessons, and also encouraged him to learn to fly. As of today, Craig has been a private pilot for 30 years!

STORY OF A HIGH PROFILE LAWYER

Upon realizing that he had a keen interest in law, he skipped continuing the engineering field and attended Vanderbilt University Law School on scholarship. In 1982, he graduated with a law degree.

The same year he graduated, Craig went to Stinson Mag & Fizzell. He was recruited by David Everson, who praised Craig’s confidence. In a year, Craig was given the opportunity of defending Hallmark Cards Inc. and other defendants in the Hyatt Skywalk Collapse. Craig had to defend his clients against a $1.5 million claim of post-traumatic stress disorder from the opposing party.  The trial gave Craig’s career the boost it needed, and he had successfully started paving his way to a thriving career.

1988 brought Craig to a law firm headquartered in St. Louis, Missouri, Bryan Cave Leighton Paisner, where he became a partner in 1990. Craig supported the non-profit organization that exonerates wrongfully convicted people, the Midwest Innocence Project, where he has been serving on the advisory board.

Mr. O’Dear’s accomplishments have been recognized in many publications. He was recognized by the Kansas City Business Journal as “Best of the Bar” in business and product liability litigation multiple times. He was also featured in the ‘Best Lawyers in America,’ Chambers USA, Missouri & Kansas Super Lawyer numerous times since 2006. Benchmark Litigation, named Craig, a ‘Missouri Litigation Star’ and the Lawdragon magazine named O’Dear, one of the Top 500 Leading Litigators in America in 2006.

In January 2018, Craig ran for Senate against Democrat incumbent Senator Claire McCaskill. He stood in the elections as an independent candidate, and a part of a Denver-based national movement of independents called Unite America and refused to caucus with either party if he would be elected. Even though O’Dear lost the election, he gained recognition by various notable personalities as an American politician because of his determination.

Today, Craig S. O’Dear lives with his family, his wife, Stephanie, in Kansas City. They have three children, daughter Sydney, and sons Cullen and Cormac.

The idea of Bigtime Daily landed this engineer cum journalist from a multi-national company to the digital avenue. Matthew brought life to this idea and rendered all that was necessary to create an interactive and attractive platform for the readers. Apart from managing the platform, he also contributes his expertise in business niche.

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Business

Royal York Property Management And Nathan Levinson On Building Stable Rental Portfolios In A Volatile Market

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Across North America, Europe, and much of the world, rental housing is caught between two pressures. On one side are tenants facing record affordability challenges. On the other side are landlords seeing operating costs, interest payments, and regulatory complexity move in the opposite direction.

Recent analysis from Canada’s national housing agency shows how tight conditions still are. The average vacancy rate for purpose-built rentals in major Canadian centres rose to about 2.2 percent in 2024, up from 1.5 percent a year earlier, but still below the 10-year average despite the strongest growth in rental supply in more than three decades. 

At the same time, higher interest rates have pushed up the cost of acquiring and financing rental buildings, which has slowed transactions and made many projects harder to pencil out.

In this environment, the question for landlords and investors is less about chasing maximum rent and more about building stability. That is where Royal York Property Management and its founder, president, and CEO Nathan Levinson have drawn attention.

From a base in Toronto, Royal York Property Management manages more than 25,000 rental properties, representing over 10 billion dollars in real estate value, and operates across Canada, the United States, and parts of Europe. Levinson also sits on a Bank of Canada policy panel focused on the rental market, where he provides data and on-the-ground insights about rent trends and landlord stress. 

For many smaller property owners, his model has become a reference point for how to treat rental housing as a structured financial asset rather than a side project.

Rental housing under pressure from both sides of the balance sheet

In many countries, the basic rental story is the same. Construction of new rental housing has climbed, yet demand still runs ahead of supply in most major cities. In Canada, overall rental supply grew by more than 4 percent in 2024, the strongest increase in over thirty years, while vacancy rose only modestly. 

At the same time, borrowing costs have moved sharply higher compared with the pre-pandemic period. Research shows that elevated interest rates have reduced the profitability of new multifamily deals and slowed investment activity, even as structural demand for rental housing stays strong.

For small and mid-sized landlords, that tension shows up in a simple way. Mortgage payments, taxes, insurance, and maintenance rarely move down. Rents move up more slowly, and in many jurisdictions they are constrained by regulation or market realities.

Levinson’s view is that this gap will not close on its own. Landlords who want to stay in the market need more predictable income, tighter control of costs, and clearer systems for dealing with risk.

A property management model built for volatility

Royal York Property Management did not start as an institutional platform. Levinson’s early clients were owners of single condominiums, duplexes, or small buildings who were struggling with irregular rent payments, surprise repairs, and complex rental rules.

Instead of handling each property ad hoc, he built a standardized operating model that treats every door as part of a wider portfolio. Each unit sits on a centralized platform that records rent, arrears, lease expiries, maintenance tickets, and legal actions. Owners see real-time statements and performance metrics rather than waiting for year-end reports.

That structure, combined with an internal maintenance and legal team, is designed to handle stress rather than avoid it. When markets are calm, the system may look conservative. When conditions worsen, it is what keeps owners in the black.

“Execution is everything” is how Levinson often frames it in interviews. 

Turning rent into a more predictable income stream

The feature that first drew many investors to Royal York Property Management is its rental guarantee program in Ontario. Under this model, landlords receive their rent even if a tenant stops paying. RYPM takes responsibility for legal proceedings, arrears recovery, and re-leasing the unit, while the owner continues to receive income.

Independent profiles of the company describe this as one of the first large-scale rental guarantee frameworks in the Canadian market, and note that the firm manages tens of thousands of units under this structure. 

The guarantee itself is closely tied to local law and does not transfer directly into every jurisdiction. The underlying logic, however, is straightforward:

  • Treat unpaid rent as a recurring and manageable risk rather than an occasional shock.
  • Price that risk into a clear product instead of handling each case informally.
  • Use scale, legal expertise, and data to keep default rates low and resolution times shorter.

For landlords who are facing mortgage renewals at higher interest rates, having a more stable rent stream can be the difference between holding a property and being forced to sell. That is one reason rental guarantee models have started to attract interest from investors outside Canada who are watching RYPM’s approach.

Using technology to see risk earlier

Behind the guarantee and the day-to-day operations is a technology stack that tries to surface problems before they become crises. Royal York Property Management’s internal platform uses data from payments, maintenance, and tenant behavior to flag risk signals and operational bottlenecks. 

Examples include:

  • Tenants who move from on-time payments to repeated short delays.
  • Units where small repair tickets point to a larger capital issue ahead.
  • Buildings where complaint volumes suggest service gaps or staffing problems.

Rather than treating these as isolated events, the system aggregates patterns across thousands of units. That allows management to decide whether a problem is individual, building-specific, or systemic.

Levinson has also pushed this data outward. As a member of the Bank of Canada’s rental policy panel, he provides anonymized information on rent collection, defaults, and renewal behavior, which feeds into broader discussions about financial stability and housing policy. 

The same data that protects a landlord’s cash flow in one building helps central bankers understand how higher rates are affecting thousands of households.

Why the Canadian case matters for global landlords

Several recent reports underline how closely rental markets are now tied to national economic performance. Tight rental supply and high rents are feeding inflation in many economies. At the same time, higher borrowing costs are discouraging new construction, which risks prolonging shortages. 

This feedback loop is especially hard on small landlords. Many own only one or two properties and have limited room to absorb higher mortgage payments or extended vacancies. Analysts in Canada and abroad have warned that some owners are at risk of default as their loans reset at higher rates. 

In that context, the Royal York Property Management model offers three lessons that travel across borders:

  1. Standardization protects both sides. Clear processes for screening, rent collection, maintenance, and legal steps reduce surprises for owners and tenants at the same time.
  2. Risk pooling is more efficient than one-off crises. Handling arrears, legal disputes, and vacancies inside a structured system is less costly than improvising each time.
  3. Operational data belongs in policy conversations. When policymakers have access to real rental data rather than only mortgage statistics, interventions can be better targeted.

It is not an accident that Levinson’s work now sits at the intersection of private property management and public financial policy.

What everyday landlords can borrow from the Royal York playbook

Most landlords will not build a 25,000-unit management platform. Many will never interact with a central bank. The core ideas behind Nathan Levinson’s approach are still accessible to smaller owners that manage a handful of properties.

Three practices stand out.

First, treat every rental unit as part of a simple portfolio. That means using a consistent template to track rent, arrears, expenses, and vacancy days for each property, then reviewing it on a schedule instead of only when something goes wrong.

Second, write down the rules for risk in advance. Late-payment steps, repayment plans, documentation standards, and maintenance response times should exist on paper, not only in memory. Royal York’s experience suggests that clear rules reduce conflict, because everyone knows what will happen next. 

Third, invest in service as a protective layer. Multiple independent profiles of RYPM point out that faster response times and transparent communication reduce tenant turnover and protect building condition, which in turn supports long-term returns. 

For landlords and investors trying to navigate today’s volatile rental markets, the message from Royal York Property Management and Nathan Levinson is surprisingly simple. You cannot control interest rates or national housing policy. You can control how organized your portfolio is, how clearly you manage risk, and how consistent your operations feel to the people who live in your buildings.

For many, that shift from improvisation to structure is what will decide whether their rental properties remain a source of wealth or turn into a source of stress.

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