The biggest turkeys of 2013

It's that time of the year when we look back and reflect on some of the worst business decisions of this annum.

Boston Globe acquisition

SLO09 boston globe

The $1.028 billion cash and stock takeover of the Globe's owner by the New York Times Co. (NYT) in 1993 is probably the worst newspaper purchase in history. And that's saying something. In October, the Times unloaded the Globe and the Worcester (Mass.) Telegram & Gazette, which it bought for $296 million in cash in 2000, for a combined $70 million. That's about 95% less than it paid. To add a drumstick, the Times Co. (as I've written before) failed to use a double horizontal dummy (love that name!) structure to do the Globe buyout, and as a result lost a $160 million tax deduction that it could have had. That makes Times Co.'s income tax bill about $60 million higher than it had to be. I take no special delight in tormenting the owner of the New York Times, a Fortune competitor. But I just can't resist cackling about a turkey deal that involves a missing double dummy. Who could?

  @FortuneMagazine - Last updated November 21 2013 01:33 PM ET
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