Photo: Bebeto Matthews / AP

Former Macy's CEO Terry Lundgren takes in on the chin in a new feature in Bloomberg Businessweek, which quotes one retail consultant as saying that Lundgren's 2005 decision to double Macy's size with the purchase of May Department Stores, was "one of the top 5 worst decisions in retail history."

Why it matters: Amazon aside, Macy's has made numerous mistakes — like doubling down on department stores the same year Amazon Prime debuted — which have hastened the retailer's decline and put it in a position to see its profits halved over the past three years.

Macy's existential test, per Bloomberg: "The premise of a department store—to be able to buy a mattress and pajamas in the same place — is still valuable. But today that place is called Amazon, and there you can buy toothpaste, too, and have it all delivered in two days. So the question is, What do department stores have that Amazon doesn't?"

  • New CEO Jeff Gennette is a Macy's lifer who believes the answer to that question is Macy's sales staff.
  • "Macy's needs to turn its associates into Apple geniuses who can engage and have personal information about their customers on their iPads," Robin Lewis, who publishes a retail strategy newsletter, tells Businessweek. "If Gennette can get personal profiles on the 10 percent of his customers who account for over 50 percent of his business, he can market to people individually, as Amazon does."

Even if Macy's executes, more closures are likely ahead: If Macy's is to succeed by selling to its core base of shoppers, that will still require the firm to shrink.

  • There are more than 660 Macy's stores in America, but CFO Karen Hoguet says that only 245 would be "critical" assets if the company were to start over today.

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