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Gary Charles Tolman

CIK 1324265 · Pres & CEO - Esurance · last filed 2025-01-03

Gary Charles Tolman is a Pres & CEO - Esurance who has filed 27 SEC Form 4 insider transactions across 2 companies since 2007. The most recent filing shows the insider was granted $119.0K of GBLI on Jan 3, 2025. Across all open-market trades the lifetime net is +$3.5M, making them a net buyer over the disclosed history. Current disclosed insider exposure totals $10.5M across reported positions. 13 SEC filings were submitted jointly with WHITE MOUNTAINS INSURANCE GROUP LTD.

"Disclosed insider exposure" sums this person's most-recently-reported share counts across each company they're an insider in, multiplied by the current underlying price. It is not net worth — it misses retail holdings, private investments, real estate, index funds, and any company where the person isn't an SEC-reporting insider. For informational purposes only.

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Disclosed Exposure

$10.53M

Companies

2

Total Filings

27

Lifetime Open-Market Net

$3.46M

Filer Profile

Reported Address
C/O GLOBAL INDEMNITY GROUP, LLC
112 S. FRENCH STREET, SUITE 105
WILMINGTON, DE 19801
Related Filers
WHITE MOUNTAINS INSURANCE GROUP LTD — 13 joint filings, latest 2018-05-25
Profile details as reported on the filer's SEC submissions — for individual insiders the address is often in care of the issuer. Related filers are identified from jointly filed SEC submissions and shared reported addresses. View filings on SEC EDGAR.

Holdings By Company

Latest on-record share count from this person's most recent non-derivative Form 4 transaction in each company. Disclosed exposure = shares × current underlying price.
Symbol Role Shares Price Disclosed Exposure Lifetime OM Net Filings Latest Filed
GBLI Director 186,587 $27.51 $5.13M $3.53M 18 2025-01-03
WTM Pres & CEO - Esurance 2,620 $2058.32 $5.39M -$71.2K 9 2018-05-25

Recent Filings

27 filings
Insider activity across all companies, newest first. Form 4 rows are post-trade confirmations (buys, sells, grants, exercises). Notice (144) rows are pre-trade notices of intent to sell restricted or control stock under Rule 144 — they may not all execute. Compare adjacent dates to see which notices became actual sales.
Filed Symbol Action Net Shares Net $ Link
2025-01-03 GBLI Grant (A) +3,411 $119.0K EDGAR
2024-10-02 GBLI Grant (A) +3,821 $119.1K EDGAR
2024-07-02 GBLI Grant (A) +3,812 $119.0K EDGAR
2024-04-02 GBLI Grant (A) +3,984 $119.0K EDGAR
2024-01-03 GBLI Grant (A) +4,286 $133.1K EDGAR
2023-10-03 GBLI Grant (A) +4,105 $138.9K EDGAR
2023-07-05 GBLI Grant (A) +4,599 $138.9K EDGAR
2023-04-04 GBLI Grant (A) +5,455 $138.9K EDGAR
2023-01-04 GBLI Grant (A) +3,114 $72.3K EDGAR
2022-12-16 GBLI Buy (P) +138,151 $3.34M EDGAR
Showing 1–10 of 27
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Form 4 codes: P = open-market purchase · S = open-market sale · A = grant/award · M = option exercise · F = tax withholding at vest · G = bona-fide gift · D = disposition to issuer · J = other (see filing footnote). Only P / S codes carry directional signal.
Notice (144 / 144/A): Form 144 is a notice of intent to sell restricted/control stock under Rule 144, filed before the sale; 144/A is an amendment. Many notices are pre-scheduled under Rule 10b5-1 plans. A Form 4 with code S typically follows within a few days when the planned sale executes; missing follow-up Form 4s suggest the notice was cancelled or modified.