Convicted swindler tries again in Tisbury

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

Tisbury Police are pursuing a larceny by check case. –Rich Saltzberg

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.


  1. Wait a minute! His name is Jeffrey (S.)Windle and nobody gives it a second thought? Is that an alias or is he just living up to his name? It occurred to me that perhaps the MV Times was having one over on us but it’s not April Fool’s Day yet.

    • Seriously! Reminds me of cracking up as a kid when I saw a skywriter spell out I.J. FOX — FINE FURS. What were his parents thinking when they gave him a middle name beginning with S? (D wouldn’t have been so good either.) Or maybe he picked it out himself?

  2. Dondondon .. I was doing the math as I read this story … how much time did he do for the crime? It sounds to me like all he learned for however long he was incarcerated was how to close on a bigger deal with an even bigger check with no funds to back it up. So, my question is who accepts a $2 million dollar personal check at closing and could it be that he was Caucasian? I have closed on property and was told well in advance I had to bring a cashiers check because personal checks were not accepted … and the amount was significantly less than $2 million … this begs the question: was I viewed as a higher risk of insufficient funds to back up that personal because I am not Caucasian and was he viewed as a lower risk or no risk individual because he wore a business suit to the closing and looked more trustworthy than me? Is this yet another prime example of institutional racism in the banking system? Maybe it is and maybe it isn’t but from my lens, it sure feels like it. It’s like going into Saks and immediately being followed by the security guard who is so busy following me they get robbed by a small crew of two innocent looking Caucasian women who entered the store directly behind me because they knew I would immediately be under surveillance by store security giving them free access steal them blind.

    • Read the article. It was a deposit not a check at closing. Personal checks are very common for a deposit. How you ever got race involved in this is perplexing.

    • I agree with John, How in the world does anyone walk away with a race issue!! I’m Caucasian and have always been required to bring a certified check. And my dealings were well under 2M.

    • P Washington —-I am sure being Caucasian helped passing the check . It likely helped him get out of jail sooner also. I doubt the racism it is as blatant as you are portraying here, but it is certainly built into the system.
      To address John Axel’s comment — just try to imagine a person of color successfully passing off a 2 million dollar post dated check after a fraud conviction.

  3. Good for Attorney Coogan! Stopped that puck! A recidivist defrauder…. 15 year sentence, probably served 1/3rd of the time which I hear is standard, then got out on parole… then what? …. please provide more history. The Vineyard seems to get one of these folks (or has homegrown its own – a real estate agent and then an attorney from Edgartown as I recall over the prior 30 years since I started coming here) every few years… More recently I recall stories about one who called herself some sort of royalty and scammed a fancy inn in Edgartown.. then there’s a lady who got control of an older house near the Tisbury School… We are part of the world after all….

  4. Jeff’s middle and last name S. Windle
    Has the potential for a good alibi at trial
    S. Windle the jurors into a not guilty finding

  5. It’s kind of hard to think anyone took this guy seriously, what with his name and prior record. But it’s a good laugh on a cold, snowy day; thanks for that!

  6. Commenters – I understand the temptation to make these jokes – but please be aware that Jeffrey has a wonderful family with deep ties to the Vineyard and these comments can sting. They are, no doubt, going through a lot now.

    • Kate you are so right…Jeffrey’s family is dear to so many of us and my heart breaks reading these comments. What Jeffrey did will be handled by the courts…if all could just take a deep breath and give his family space that would be a great blessing.

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