Look, let’s get it straight up front: Harlan Crow is still young as executives go, extremely active in his business, and the real estate mogul is planning to helm Crow Holdings for a long time to come.

Checking it twice: Raymond with her list of signatures. photography by Joshua Martin
Still, people can’t help but notice the increasingly prominent role Anne Raymond plays as Crow’s “right-hand man” (her words) for the bulk of the last 25 years. She’s second only to Crow in the power she wields, and it seems to several commercial real estate veterans like she’s taking an increasingly public role in the company. Aside from being Crow Holding’s second-in-command (managing director is her title; capital markets, portfolio management, and financial reporting are her charges), Raymond also heads up the organized effort to derail the planned city-owned and subsidized convention hotel.

Her role with the anti-hotel group isn’t some honorary, lead-from-the-rear generalship. To back her position, she coolly rattles off facts, figures, and studies like a pink-suited Mr. Spock to anyone who will listen. Yes, her effort has a strong self-interest and there is corporate money behind it. But Raymond is also out building neighborhood-level support most mornings before she even hits the office.

“I’m meeting tomorrow with a neighborhood mom group to talk about this after we drop off our kids,” she says.

Later that day, Raymond will be back in her managing director role, discussing the $950 million private equity fund Crow Holdings just started to look for post-crash real estate opportunities.

“We sold most of our stuff in 2006 and 2007 when it peaked,” she says. “We don’t know when the bottom will hit, but we will find it. We’re looking all over the country to the horizon.”