The house that Jack built

imageJack’s house, Woodbury, Connecticut © Steven Willard

I never met Jack. In fact I don’t even know if that is real name, but around town he is known as Cadillac Jack. I didn’t get it until I stopped to take some photographs of his place the other day.

Jack’s place isn’t far from town, but it’s on a road I don’t frequent, and so I was surprized, when I drove by recently, by just how derelict it had become; windows broken, weeds grown up all over the place, and no sign of recent work. Clearly something had happened to Jack and that didn’t bode well.



Around the property there was evidence of Jack’s work in progress, but work in progress halted, almost in mid stride. I-beams, left half in, half out of a window, as if he had been called away in the middle of a project. Slate for the roof left on the barrow, and the barrow dropped on the path.




It had been some time since Jack had paused to sit down for a moment to look upon his handiwork. Did he reflect on what a large undertaking he had set for himself? To set out out to build a house, a very large house of stone, all by himself.  Everywhere I looked there are projects started, seemingly on a whim, but nothing actually finished. The place had become a folly by all definitions. But there was more….




Around the side of the house I see where he got his name; Cadillacs in very sorry shape, obviously wrecks that he had claimed, roofs crushed, doors caved in and windows broken. These were cars that would need a lot of attention (and a lot of money) to make whole again. What was he thinking? That he would live forever?*

Here was a man who set himself gigantic tasks, impossible tasks; a modern man of La Mancha, who dared to dream impossible dreams. I would have loved to have known him.

*I do not know if is still living, but I fear he is not. The property has the look of neglect I can only imagine existing if he were no longer around.

Olympus OMD EM5 wit 14-42mm kit zoom, processed on my iPad Air.


7 comments on “The house that Jack built

  1. Marc Isolda says:

    great shots and great dialog very insightful !


  2. dmglostne says:

    fantastic shots and great blog love your format. When did you take the photographs I would like to go check it out David lostinnewengland


  3. nikkorbacher says:

    Aretha Franklin?


  4. nikkorbacher says:

    Your title reminded me of the Aretha Franklin song of the same title:


  5. I’ll have to take your word for it.


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