Cal 40 Sailing

Montgomery Street

Hull #55 • Fleet Gallery & Historic Record

Boat Profile & History

Montgomery Street — Hull #55


Photos

Boat Data

  • Hull Number: 55
  • Sail Number: 8555
  • Boat Name: Montgomery Street

Owner Data

  • Current Owner: David Denning (Family legacy established by Jim Denning in 1969)
  • Email: DavidJDenning@yahoo.com
  • Homeport / Location: Richmond, CA

History & Chronicles

The Denning family began their multi-decade involvement with the Cal 40, Montgomery Street, in the spring of 1969. True to his nature, Jim Denning didn’t tell anybody of his plans to trade in the 30-foot, wooden, Hurricane Class Sloop that he built and launched in 1958.

When the Cal 40 pulled into their slip on the San Rafael Canal, she looked like a gold-plater mega-yacht compared to the Hurricane. In the 1960s, a forty-footer was a large boat! Stepping aboard revealed vast amounts of room: comfortably sleeping eight without requiring someone to leave their bunk to access the head.

As the broker demo boat, she was fully equipped for ocean racing with state-of-the-art bronze Barient 2-speed winches, harnesses, strobes, and pristine new finishes, making the Dennings her first "owners." Jim dreamed of racing a Transpac, and at age 55 with limited ocean racing experience, he bought the boat. After numerous Lightship and Windjammer races, the boat embarked on a rich racing legacy spanning decades of YRA, Danforth series, Mazatlan, Cabo, and Transpac races (competing in every Transpac from 1969 through 1991 except 1979).

Over the years, Montgomery Street underwent major custom optimizations—including a complete bottom surgery in 1982 at Cal Coast Marine featuring a new custom lead keel engineered by Les Harlander, a new 2-spreader mast, modified bulkheads, and a Volvo diesel engine. Following Jim Denning's passing in 2002, David Denning undertook an extensive restoration of the interior woodwork, topsides, deck hardware, and hull coating, keeping this iconic Cal 40 vibrant and active on the San Francisco Bay.

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