Allstate vs Cincinnati Financial: Founders, CEOs and History
Allstate was founded in 1931 by Sears, Roebuck and Co. and is led by Tom Wilson. Cincinnati Financial was founded in 1950 by John J. (Jack) Schiff, Robert C. (Bob) Schiff, Harry M. Turner and is led by Stephen M. Spray.
Company facts
Allstate
- Founded
- 1931
- Headquarters
- Northbrook, Illinois
- Current CEO
- Tom Wilson
- Employees
- 53,300
Cincinnati Financial
- Founded
- 1950
- Headquarters
- Fairfield, Ohio
- Current CEO
- Stephen M. Spray
- Employees
- 5,420
Founders
Allstate
Sears, Roebuck and Co.
Sears created Allstate Insurance Company as a subsidiary in 1931. Allstate initially sold auto insurance by direct mail through Sears catalogs, placed its first agent in a Sears booth at the 1933 Century of Progress fair, and began operating agent offices in S…
Cincinnati Financial
John J. (Jack) Schiff
Jack Schiff co-founded The Cincinnati Insurance Company in 1950 with his brother Bob and fellow agents Harry M. Turner and Chester T. Field. The company says he never stopped seeing himself as an agent first.
Robert C. (Bob) Schiff
Bob Schiff was 26 when he co-founded The Cincinnati Insurance Company in 1950. With his brother he helped build the agent-sponsored model, including working Saturdays to meet agents and policyholders, a habit associates continued for decades.
Harry M. Turner
Harry M. Turner co-founded Cincinnati Financial in 1950 alongside his brothers. He deeply understood that independent insurance agents were increasingly alienated by massive corporate carriers, leading him to base the company's entire philosophy around serving…
Chester T. Field
Chester T. Field partnered with the Turner brothers to establish Cincinnati Financial in 1950.
CEOs and their tenures
Allstate
- Wayne E. Hedien1993–1994
Former Chairman and Chief Executive Officer
Hedien led Allstate during its 1993 initial public offering, when Sears sold 19.8 percent of the company.
Source - Jerry D. Choate1994–1998
Former Chairman and Chief Executive Officer
Choate was elected president and chief executive officer on August 10, 1994 and became chairman on January 1, 1995.
Source - Edward M. Liddy1999–2006
Former Chairman and Chief Executive Officer
Liddy served as chairman and chief executive officer from January 1999 through the end of 2006 after serving as president and chief operating officer from 1994 through 1998.
Source - Tom Wilson2007–present
Chair, President and Chief Executive Officer
Wilson became CEO on January 1, 2007 and chair in May 2008. The 2025 Form 10-K identifies Transformative Growth and multichannel distribution as current strategic priorities.
Source
Cincinnati Financial
- Steven J. Johnston2011–2024
Chairman (CEO 2011-2024)
As CEO since 2011, he successfully navigated the company through severe natural disaster cycles, expanding commercial lines into excess and surplus (E&S) markets to drive higher margins.
Source - Stephen M. Spray2024–present
President and Chief Executive Officer
Appointed as President in 2024, he oversees all day-to-day operations, attempting to balance the company's historic reliance on independent agents with necessary digital modernization.
Source
Timeline: Allstate and Cincinnati Financial side by side
1931Allstate
Allstate launches
Allstate Insurance Company opened on April 17 as a Sears mail-order auto insurer. Its first policy covered a 1930 Studebaker for $41.60 a year.
1933Allstate
First Allstate agent booth
The first Allstate agent sold policies from a card table in the Sears Roebuck booth at Chicago's Century of Progress fair. Agents began working in Sears stores in 1934.
1939Allstate
Risk-based auto rates introduced
Allstate began tailoring auto rates by the driver's age, mileage, and use of the car.
1947Allstate
Illustrator Policy debuts
Allstate introduced an insurance policy that used plain language and illustrations to explain coverage.
1950Allstate
Good Hands slogan begins
Allstate adopted the You're in good hands slogan developed by sales executive Davis Ellis.
1950Cincinnati Financial
Four agents found The Cincinnati Insurance Company
Jack and Bob Schiff, Harry M. Turner and Chester T. Field organize an agent-sponsored property-casualty insurer in Cincinnati.
1952Allstate
Allstate Foundation created
Allstate established The Allstate Foundation, which initially supported driver education and community programs.
1959Allstate
Catastrophe response plan launches
Allstate created a plan to deploy large teams of claim specialists immediately after disasters.
1967Allstate
Headquarters moves to Northbrook
Allstate moved its headquarters to a 122-acre, six-building complex in Northbrook, Illinois.
1968Cincinnati Financial
Holding company formed
Cincinnati Financial Corporation is created as the parent company, enabling expansion into life insurance and other businesses.
1984Allstate
Neighborhood Office Agent program
Allstate introduced neighborhood agent offices. By year-end, 1,582 agents worked at 944 locations.
1993Allstate
Allstate initial public offering
Sears sold 19.8 percent of Allstate in what Allstate identifies as the largest U.S. IPO to that date.
1995Allstate
Full separation from Sears
Sears distributed its remaining Allstate shares to Sears shareholders, making Allstate fully independent and publicly held.
2000Allstate
Online purchasing begins
The Good Hands Network launched in Oregon, allowing customers to buy auto insurance online, by telephone, or through an agent.
2008Cincinnati Financial
Cincinnati Specialty Underwriters begins writing E&S
The company enters excess and surplus lines through its own new carrier, serving risks standard insurers decline.
2010Allstate
Drivewise begins
Allstate began offering Drivewise to reward low mileage and safe driving measured by a telematics device. Drivewise Mobile followed in 2014.
2011Allstate
Esurance and Answer Financial acquired
Allstate closed its $1 billion cash purchase of the Esurance business and Answer Financial on October 7.
2017Allstate
SquareTrade acquisition closes
Allstate completed its acquisition of consumer protection plan provider SquareTrade on January 3.
2018Allstate
InfoArmor acquired
Allstate announced on October 5 that it had completed its acquisition of identity protection provider InfoArmor.
2019Cincinnati Financial
Lloyd's entry via MSP Underwriting
Cincinnati Financial acquires MSP Underwriting, manager of Syndicate 318 at Lloyd's, later renamed Cincinnati Global Underwriting.
2020Allstate
Shelter-in-Place Payback
Allstate returned almost $1 billion to auto customers over three months after pandemic restrictions reduced driving.
2021Allstate
National General acquired
Allstate completed its acquisition of National General on January 4, making National General a wholly owned indirect subsidiary.
2024Cincinnati Financial
Stephen M. Spray becomes CEO
Spray takes the CEO title at the May 4, 2024 annual meeting; Steven J. Johnston remains chairman.
2025Allstate
Health businesses sold
Allstate closed the employer voluntary benefits sale on April 1 and the group health sale on July 1, recording pretax gains of $888 million and $715 million.
2025Cincinnati Financial
Record revenue and book value
Revenue reaches $12.631 billion and book value per share a record $102.35 despite a first-quarter loss from catastrophes.
2026Cincinnati Financial
66th year of dividend increases
The quarterly dividend rises 8% to $0.94; the October 2026 payment completes 66 consecutive years of higher annual dividends.
Acquisitions
Allstate
- National General Holdings Corp.2021$4B
- InfoArmor2018$525M
- SquareTrade2017$1.4B
- Esurance and Answer Financial2011$1B
Cincinnati Financial
- MSP Underwriting (Syndicate 318 at Lloyd's)2019$134M
- CSU Producer Resources (Specialty Lines Brokerage)2008Undisclosed
- The Cincinnati Life Insurance Company1963Undisclosed
Questions about Allstate vs Cincinnati Financial
Who is the CEO of The Allstate Corporation and Cincinnati Financial Corporation?
The Allstate Corporation is led by Tom Wilson and Cincinnati Financial Corporation is led by Stephen M. Spray. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was The Allstate Corporation founded vs Cincinnati Financial Corporation?
The Allstate Corporation was founded in 1931 — 19 years before Cincinnati Financial Corporation, which was founded in 1950. The Allstate Corporation's longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Cincinnati Financial Corporation.
How many employees does The Allstate Corporation have compared to Cincinnati Financial Corporation?
The Allstate Corporation employs approximately 53,300 people, while Cincinnati Financial Corporation employs approximately 5,420. The Allstate Corporation has the larger workforce at 53,300 employees, compared to Cincinnati Financial Corporation's 5,420. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are The Allstate Corporation and Cincinnati Financial Corporation headquartered?
Both The Allstate Corporation and Cincinnati Financial Corporation are headquartered in United States. Their local rules and tax obligations may still differ.
Who founded The Allstate Corporation and Cincinnati Financial Corporation?
The Allstate Corporation was founded by Sears, Roebuck and Co.. Cincinnati Financial Corporation was founded by John J. (Jack) Schiff, Robert C. (Bob) Schiff, Harry M. Turner, Chester T. Field.
Which company has a longer operating history — The Allstate Corporation or Cincinnati Financial Corporation?
The Allstate Corporation has been operating for approximately 95 years, making it the more established of the two companies. Cincinnati Financial Corporation has been in operation for around 76 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Allstate vs Cincinnati Financial overview