Convicted swindler tries again in Tisbury

Jeffrey Windle charged with passing a bogus $2 million check.

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Tisbury Police department in Vineyard Haven.

Updated Feb. 23

Tisbury Police have charged a convicted embezzler with larceny over $1,200 and larceny by check for $1,200, both felonies, for placing a deposit on a $15 million Edgartown property with a $2 million check that was drawn on an account with insufficient funds. Jeffrey S. Windle allegedly signed a purchase and sale agreement at Geoghan Coogan’s law office in Tisbury on Jan. 18, and provided a personal check for $2 million to that law office on Jan. 22 that was dated Jan. 23, according to a police report. Windle allegedly attempted to delay the deposit of the personal check by promising a cashier’s check, a report states, but that never came. He later allegedly provided excuses that his father had died to both the law office and the sellers. At some point in dealing with Coogan, he allegedly also employed the name Jeffrey Leonard, according to a report.

On Jan. 29, Attorney Coogan brought the check to Martha’s Vineyard Bank, where the check hailed from, and attempted to deposit it, but was told there were insufficient funds to cover the sum, a police report states. 

On Feb.12, Oak Bluffs Police assisted U.S. Marshals task force members in locating Windle at an address in Oak Bluffs and apprehended him, according to a report. 

“Officers knocked at the door, Windle came to the front porch, and Windle was taken into custody without incident on a federal probation violation,” a report states. “[U.S. Marshals Service] officers took Windle into custody and transported him to Plymouth for booking.”

On Saturday, Coogan declined comment on Windle. 

In 2009 Windle admitted to embezzling millions, including one lump sum of $647,000, from the Congregational Church of South Dennis, the Patriot Ledger previously reported. He received a 15-year sentence, the Cape Cod Times previously reported.

Updated with additional details from Oak Bluffs Police.