Edmund Ashford opened the firm in 1932 with a hand-painted shingle, a Royal typewriter, and three accounts: the New Hope Fishing Cooperative, the Mead family estate on Round Hill Road, and his own cousin's automobile policy. The Mead family is still a client.Founder · First Generation
Edmund Ashford, 1932–1958
Edmund Ashford was a Greenwich High School graduate, a Yale undergraduate, and a Hartford-Aetna trainee before he opened the firm at thirty-one in a brownstone on Greenwich Avenue. His first office was two rooms above a fishmonger; the smell of the harbor came in through the windows in summer and the cold off the Sound in winter. He kept the same address until 1948.
The Hurricane of 1938 was Edmund Ashford's first stress test. Forty of the firm's policyholders had property damage; eleven had total losses. He drove a borrowed truck up Long Island Sound for five days adjusting claims on behalf of his carriers, sleeping in the cab between visits. The firm did not lose a single client in the year following.
The wartime years were difficult — carriers placed moratoria on new commercial lines, gasoline was rationed, the local fishing fleet was conscripted for coastal patrol — but Edmund kept the firm intact by writing the personal-lines and farm-property programs for the families whose sons had gone to Europe and the Pacific. He hired Theodore Whitcombe Sr. (his nephew through his sister Eleanor, who married into the Whitcombe family of New London) in 1947 as the firm's first full-time producer beyond the founder.
The postwar boom in coastal property — Greenwich's transformation from a fishing village into the leading edge of New York's exurban wealth — was the wave Edmund rode through his last decade in the business. By 1958, when he retired, the firm represented fourteen carriers and held approximately one and a half million dollars in premium across roughly four hundred and forty households.
Second GenerationTheodore Whitcombe Sr., 1958–1989
Theodore Whitcombe Sr. — Edmund's nephew and the second generation by lineage if not by surname — took the firm through what was, in retrospect, the formative thirty years of modern American property-and-casualty insurance. Long-tail liability emerged. Commercial general liability replaced the older comprehensive personal liability form. Personal umbrella policies were invented. The firm wrote its first such umbrella in 1962 — for the family of a Stamford pharmaceutical executive who had begun keeping horses on his property.
In 1967 the firm moved to its current Field Point Road address — a four-story Federal-style brownstone built in 1872 that had been a doctor's office, a small bank, and a Greenwich Realtors' Association headquarters before Theodore Sr. bought it. The conference room is still in the front parlor; the partners' offices are on the second floor.
The 1970s brought the first commercial-account practice as a distinct service line. The firm's longstanding personal-lines households — the same families whose grandfathers Edmund had insured — were now running operating businesses, foundations, and family offices. Theodore Sr. recognized that the firm needed an integrated benefits practice; he hired the firm's first dedicated benefits producer in 1973. By 1989, when he retired, the firm wrote approximately seven million dollars in premium across personal lines, commercial, and benefits.
Third GenerationTheodore Whitcombe Jr., 1989–2014
Theodore Whitcombe Jr. — Theodore Sr.'s eldest son, Edmund Ashford's grand-nephew — took the firm into the modern HNW-private-client era. In 1991 the firm was appointed a Chubb Cornerstone Agency, joining an invitation-only roster of approximately sixty agencies nationally that Chubb identified as its premier private-client partners. The appointment defined the firm's trajectory for the next thirty years.
Theodore Jr. formalized the Private Client practice as a distinct service line in 1994 — separating the HNW households, with their fine-art schedules and coastal-secondary-home programs, from the commercial accounts that the firm had grown alongside since the 1970s. He authored what is now the Ashford Review™ methodology, originally as an internal training document for the firm's producers.
The 2001 acquisition of the Devanney Agency — a five-producer firm in Stamford with deep relationships across Westchester County and a strong workers-compensation book — brought Patricia Devanney into the firm as a partner. (She remains one today.) By 2014, when Theodore Jr. retired to teach insurance at the University of Connecticut, the firm wrote approximately twenty-six million dollars in premium and represented eleven carriers.
Fourth GenerationTheodore Whitcombe III, 2014–present
Theodore C. Whitcombe III — Ted, to most of the firm and most of his clients — assumed the senior partnership in 2014 at the age of forty-nine. He holds CPCU, CIC, and AAI designations; he serves on the Big "I" Best Practices study committee; he has chaired the Connecticut Independent Insurance Agents association's Coastal Property Committee since 2018.
In 2017 the firm received its first Big "I" Best Practices Agency designation — an annual recognition awarded to roughly the top five percent of independent agencies nationally on operational excellence, financial health, client retention, and growth. The firm has been on the list every year since.
In 2019, Ted's daughter Margaret Whitcombe-Lockhart opened the Newport office to extend the private-client practice into Rhode Island. The same year, the firm formalized the Ashford Review™ as a named program, with a written methodology distributed to producers and a standardized client deliverable.
The firm has received three acquisition offers from national rollups since 2014 — each declined. The most recent, in late 2023, would have given the named partners a comfortable exit and made each producer materially wealthier. The partners voted against the transaction.
We were offered three acquisitions in the year leading up to the Newport opening. Each would have given the partners a comfortable exit and made each producer materially wealthier. We declined them — not because the offers were unfair but because the work the firm does is not the work a roll-up does. The work is conducted at conference tables, with read-out reviews of existing programs, with carriers who answer the phone when a claim moves to a coverage dispute. Selling the firm would have ended that work — and we are not done. — Theodore C. Whitcombe III, Insurance Journal interview, 2024Fifth Generation
Margaret Whitcombe-Lockhart, 2019–present
Margaret Whitcombe-Lockhart — Ted's eldest daughter and the first of the fifth generation — joined the firm as a producer in 2011 after Ohio State and Northwestern Kellogg, and completed the CPCU coursework while carrying a full personal-lines book. She holds CPCU and ARM. She opened the Newport office in 2019 with a single account executive and a Marine producer; the office now holds four producers, one CSR, and writes approximately nine million dollars in premium.
The Newport office's specialty is marine and aviation. Helena Burroughs, a CPCU and former Travelers Yacht underwriter, joined as a partner in 2020 and runs that practice — placing watercraft and aviation programs that the standard private-client carriers will not write. The office serves Rhode Island, southeastern Massachusetts, Block Island, Nantucket, and Martha's Vineyard.
Margaret authored the Cornerstone Coastal™ program in 2022 — formalizing a coordination methodology the firm had practiced informally for over a decade — and is co-author, with Robert Tan, of the Steward's Brief™ document delivered quarterly to family-office clients.
RecognitionThe Best Practices designation
The Big "I" Best Practices study is conducted annually by the Independent Insurance Agents & Brokers of America and Reagan Consulting. It identifies agencies in four revenue tiers that demonstrate top-quartile performance on a range of operational, financial, and growth measures — client retention, producer productivity, organic growth rate, EBITDA margin, balance-sheet strength, and reinvestment in technology and staff development.
Agencies on the list are reviewed annually; designation is not automatic. The firm has appeared in the study every year from 2017 through 2026. For a Northeast independent agency of our size, the recognition is significant — but it is also, internally, used as a yardstick: we ask the same questions of ourselves every year that the study asks of us.
Awards and memberships
- Big "I" Best Practices 2017, 2018, 2019, 2020, 2021, 2022, 2023, 2024, 2025, 2026
- Chubb Cornerstone Agency (1991–present)
- PURE Insurance Cornerstone Partner (2008–present)
- Cincinnati Insurance Diamond Agency
- CPCU Society (multiple producers)
- Risk and Insurance Management Society (RIMS)
- International Risk Management Institute (IRMI) — Premium Member
- Council of Insurance Agents & Brokers (CIAB)
- National Association of Professional Insurance Agents