New Canaan Man Is Buying Up Heritage Hill Road Condos

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A New Canaan man through a limited liability company he controls has spent about $3.7 million in 2016 to acquire 10 of the Heritage Hill Road condominiums, as well as four garage units there, land records show.

The condominiums at Heritage Hill Road. Credit: Michael Dinan

The condominiums at Heritage Hill Road. Credit: Michael Dinan

Thomas Hudson of West Road, identified as a financier and former hedge fund manager in national news stories about him, is principal of Captain Jack LLC, according to records on file with the Connecticut Secretary of the State.

Through Captain Jack—Hudson has been described as a pirate enthusiast—he acquired the following units at the ‘Oenoke Apartments Condominium’:

Captain Jack-Acquired Heritage Hill Road Condos

UnitSelling PriceProperty Transfer Date (all 2016)
62C$435,000Jan. 27
83A$362,500June 2
64C$275,000June 14
72B$354,000July 8
167A$382,500July 8
76B + garage$325,000Aug. 10
86 + garage$450,000Aug. 10
66A + garage$300,000Aug. 31
80C$300,000Aug. 31
61 + garage$495,000Sept. 23
*Source: New Canaan Land Records


It isn’t clear whether the purchases represent a straight real estate investment—single-level units close to the downtown are in demand, officials say—or if something more involved is planned for the 1960s- and ‘70s-built complex.

Hudson could not be reached for comment. A local attorney who has handled the property transfers for him—Michael Murray of Ivey, Barnum & O’Mara LLC—said “No comment” when reached by The head of the Oenoke Association, a homeowners’ group at the condos, also declined to comment on the matter.

Hudson is founder of the hedge fund ‘Pirate Capital LLC,’ according to multiple news articles that appeared in the New York Times and other national publications. The company employed pirate imagery and used the term “surrender the booty” in activist investor dealings, one article said. According to a 2014 Wall Street Journal article, Hudson also had been owner of a pirate-themed estate on St. Thomas that he named ‘Villa Whydah’ after a sunken 18th-century pirate ship near his childhood home.

It could be that ‘Captain Jack LLC’ refers to Johnny Depp’s character, Capt. Jack Sparrow, in the “Pirates of the Caribbean” film series. There also is a Billy Joel’s “Captain Jack” (see video below), though the reference there appears to be to substances—perhaps Jack Daniels whiskey—and the song itself describes a feckless 21-year-old whose mother still makes his bed.

According to tax records, Hudson purchased his home in New Canaan three years ago. Town officials last year cited violations of New Canaan’s Inland Wetlands regulations at his property.

Billy Joel – Captain Jack (from Live at Shea Stadium)

In 2008, Billy Joel commemorated the closing of the New York Mets stadium, Shea Stadium, with a legendary two-night concert of his top tracks as well as amazing guest performances. Watch here as Billy and his band perform ‘Captain Jack’ off the 1973 album Piano Man.


8 thoughts on “New Canaan Man Is Buying Up Heritage Hill Road Condos

    • Thanks Mike. That does make more sense than whiskey, though I will say in either case there is no obvious connection to pirates, who are said to like rum, so Billy Joel probably did not inspire the name of this LLC.

  1. He is probably buying these units in the expectation that he will be able to obtain a waiver to a P&Z rule and will replace them with twice as many. Why can’t P&Z ever say no to a developer? How can we have any confidence that the rules will be applied fairly? Who is running New Canaan? The town residents or the developers?

  2. I lived in one of the apartments he bought. He is going to buy them up and make it 3 x’s as big. Just get ready for it and too bad if P+Z receives thousands of letters in opposition, they don’t care. Build em high!

    The only recourse we have is to VOTE OUT our leaders who appoint people that don’t care about conserving our town’s charm and character. They will say we don’t have the ‘facts’ or the ‘data’, but we don’t need 500 more condos in NC, we just don’t. Improvement? Yes, overdevelopment? NO.

  3. The rest of the owners in this complex should pay close attention to this. If one owner owns more than 10% of all units in the complex the complex becomes unwarrantable with regard to conventional lending. If that is or becomes the case owners may have difficulty selling to buyers with conventional mortgages who won’t lend for that complex. Why does that matter? If this one individual is able to control the market in this complex he may be able to start forcing prices here down if sellers are unable to to sell to anything other than all cash buyers.

  4. Two quick notes for the reader who submitted a comment under the username ‘Scally Wag’ and email address ‘’ that ends with this sentence: “… It’s a family business with family values.” First, please know that our CMS captures your IP address when you submit a comment. As a rule, we do not publish comments from aliases—even hysterically funny ones like yours—and we need a working email address to verify identities. Second, if I’m reading your comment right and you feel defensive of this company, please just phone or email me (cell is 203-817-1278, email so that we can discuss it. In your submitted comment you identified a minor in a negative context, and we do not allow that either, which is why I chose not to reproduce the full comment here.

  5. Our P+Z Commissioners’ unanimous approval of M2Partners development of Merritt Village from 38 units to 110 units, despite public outcry from over 1,000 residents who signed petitions, despite over 150 letters and e-mails gathered in just 3 weeks, has now opened the floodgates for other developers to do likewise. The threat of 8-30g is just a bully tactic. Heritage Hill will be another.
    EB’s comment is spot on. The writing is now on the wall for more high density pocket development throughout town, more traffic congestion, lower property values, and higher school enrollment.
    And, yes indeed, the P+Z decision will change the small town character and charm of New Canaan forever.

  6. Interesting article Mike, gone is the stigma of New Canaan known for their “McMansions”.
    The new name going around is “New Condo”.

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