An insurance company can sell the right to its next chapter and still have to finish the previous one. In October 2025, Everest agreed to transfer renewal rights for its global retail commercial insurance business to AIG. The business represented about $2 billion in annual premiums. Existing liabilities would stay with Everest, along with responsibility for administering claims on its policies. A corporate change of direction would leave a substantial amount of work pointing backwards.
Three weeks later, Everest announced that Gary Haase would join as executive vice president and CEO of Legacy Operations. His appointment took effect on December 1. He would report to president and CEO Jim Williamson and join the executive leadership team. The assignment was to manage the legacy insurance portfolios, improve the use of capital and bring operating discipline to the business.
It was a job for someone who understood what happens after the announcement. Haase had spent more than a decade at Catalina, an insurance run-off specialist, before becoming chief operations officer at CNA. His experience ranged from actuarial work and reinsurance to acquisitions, technology and analytics. He had also taught statistics. Insurance had given him several ways to examine the same uncomfortable object: an obligation whose eventual cost remained uncertain.
Everest now lists his title as Executive Vice President, Capital Solutions. The wording suits a career in which old portfolios and future decisions keep meeting. A promise made years ago can still determine what a company is able to do tomorrow.
The work after the acquisition
Haase began his career in actuarial and reinsurance roles at Aon Benfield and Quanta U.S. Holdings. Those are useful places to learn that a premium collected today and a claim paid later belong to one transaction, even when they sit years apart. The arithmetic comes with a calendar attached. Assumptions have to survive the interval.
By the time he left Catalina for CNA in 2021, he had become Group COO. His responsibilities included due diligence, integration and the continuing management and performance of acquired companies. He also held CEO and director roles within the group, including leadership of its U.S. and Bermuda businesses. It was experience in buying a business and then living with it.
That last part deserves some attention. An acquisition announcement compresses a company into a name and a price. Integration restores the missing detail: people doing particular jobs, systems holding particular records, businesses operating in different jurisdictions. Haase’s Catalina remit extended across that less photogenic territory. There is no ribbon-cutting ceremony for making inherited operations function together.
A Connecticut regulatory decision supplies a concrete example of the responsibilities behind those group titles. In the proposed acquisition of Sparta Insurance Company, the post-acquisition leadership list named Gerald “Gary” Haase as both a director and chief executive officer. The document puts him inside the governance of an individual insurer, beneath the broader Catalina organization.
That is a different level of detail from an executive biography. A group operating role can encompass several businesses. A company directorship and CEO appointment attach the work to a particular legal entity. Haase’s record includes both perspectives, which helps explain why later employers could describe his experience in terms of transactions as well as continuing management.
Run-off gives the work a particular shape. A portfolio can stop taking new business while its existing obligations continue to require management. Claims, reinsurance arrangements and operating costs still matter. The calendar keeps moving even when the sales machine has stopped. Haase’s later appointments repeatedly drew on this combination of liability knowledge and practical operating experience.
About $2bn in aggregate premiums was associated with the renewal rights. That figure describes the business, not the purchase price.
A teacher’s other classroom
There is an academic strand running alongside the operating jobs. Haase holds a bachelor’s degree from the University of Iowa and an MBA from New York University’s Stern School of Business. His MBA studies included quantitative finance and general management. He also served as an adjunct associate professor of statistics at Stern, teaching graduate-level statistics and data analysis.
He became a Fellow of the Casualty Actuarial Society in 2006. The credential places formal actuarial training underneath the later executive titles. It also helps explain the range of his professional vocabulary: he has worked with both the estimates used to understand insurance liabilities and the organizations responsible for managing them.
The teaching connection offers an interesting way to read that career. A statistical result needs an explanation before somebody else can use it. An operating decision needs one too. In each setting, the calculation has to reach people who are expected to act on it. Haase’s record puts the classroom and the executive role unusually close together.
An assembly line for old data
CNA hired Haase in 2021 as part of a leadership change intended to expand its use of analytical technology. He succeeded Michael Costonis as chief operations officer as Costonis moved into a role covering marketing, strategy and innovation. Then-CEO Dino Robusto connected Haase’s arrival to the wider use of data in operational decisions.
At CNA, Haase’s responsibilities stretched across technology, analytics, operations, procurement, real estate and resiliency. The list is a useful corrective to the idea that an executive interested in data spends the day considering models. There were also buildings, suppliers and the continuing business to consider. The analytical ambitions sat inside an operating job.
In a May 2022 interview, he described an automated approach to moving CNA’s accumulated data into the cloud. Migration speed had increased tenfold over the preceding year, he said, and the company was roughly 90 percent through a three-year plan in half the expected time. Data from different claims systems was being organized into a common format using Google BigQuery.
The intended applications included identifying potentially fraudulent claims and spotting liability cases that might develop into large verdicts. These were uses he discussed, rather than a claim that every proposed model had already delivered a result. He also described the importance of human service alongside digital portals and chatbots.
In July 2022, he joined CNA’s data and analytics leader Santosh Bardwaj for a Casualty Actuarial Society webinar on cloud analytics. That pairing put an operating executive and a data executive in the same educational conversation. It also returned Haase to an audience familiar with the problems behind insurance numbers.
Historical progress reported by Haase at the time; these are migration figures, not investment returns.
An actuary at the AI table
After CNA, Haase advised private equity and technology firms on insurance acquisitions and transformation. The combination brought together two familiar parts of his working life: transactions and the operations expected to make them worthwhile. His advisory experience also included artificial intelligence.
In June 2025, Exelixi AI announced an advisory board that included Haase, Edward Altman and Walter Gontarek. Altman is associated with research into corporate financial distress; Gontarek brought financial-services and academic experience. Haase brought insurance operations and analytics. His own announcement emphasized AI applications for insurers and financial services.
The appointment places his interest in AI before the move to Everest. It follows the earlier work of making insurance data available for analysis at CNA. The technologies had moved on; the practical setting remained recognizable. Insurance businesses had records, decisions and obligations for which better information could be useful.
The June announcement also identified him as a board member of Bermuda-based Fleming Insurance Companies. By that point his career included running operations, overseeing acquired businesses, teaching and advising. The breadth stayed concentrated around insurance and financial services, where an attractive idea still has to work inside an existing institution.
The past earns its place
At Everest, the corporate circumstances gave that background a clear application. The company was sharpening its focus on reinsurance, global wholesale and specialty insurance. Haase’s appointment followed the decision to transfer retail renewal rights. Williamson pointed to his combination of actuarial, claims, transaction and technology experience when explaining the hire.
The chronology matters. Haase arrived after the renewal-rights agreement was announced. His assignment addressed the portfolios that still needed to be managed as Everest changed direction. A company can choose where it wants to write new business. Its existing policies have their own timetable, and policyholders retain an interest in how that timetable is handled.
By the 2026 Monte Carlo reinsurance gathering, Haase was discussing the relationship between legacy business and active insurance markets. Speaking at PwC’s Legacy Live event, he framed legacy operations as a contributor to the rest of the company’s capacity to act. Everest shared his description of legacy as a capital engine.
“legacy is a living capital engine for the rest of the company”
Gary Haase · PwC Legacy Live, RVS Monte Carlo, 2026
In his own account of the Monte Carlo discussion, he thanked Andrew Ward and the PwC team and described an opportunity to build a long-term legacy platform around expertise, talent and technology. The formulation brings people into a conversation easily dominated by capital. An operating platform needs judgment and execution as well as a financial purpose. Read alongside his earlier responsibilities, the ambition has a recognizable scope: acquired businesses to understand, information to organize and portfolios to manage over time. The latest role gives those accumulated skills another setting, within an insurer whose new-business strategy has changed while its earlier commitments continue.
That is a useful place to leave his story for now. The actuary’s concern with liabilities, the operator’s concern with execution and the teacher’s concern with making information usable all appear in his career. At Everest they meet around portfolios that belong to the company’s past and continue to influence its choices. Insurance promises are rather stubborn that way: they expect somebody to stay until the business is finished.
Follow the working life
Appointments, conversations and further reading.