Mid-decade, Terry Semel was the envy of his peers: an old-media exec who through luck and judgment had landed the internet's top job, boss of Yahoo. The photos show how Yahoo's troubles wore him down. For Valleywag's memorial wall, keep reading.
At the end of 2005, when Yahoo's stock broke through $40. That was the peak of Semel's tenure. A few small acquisitions such as Flickr, the photo service, had given Yahoo a dash of glamor. And that drew attention away from the company's defeat in search.

For Terry Semel, the former Hollywood studio exec, the entertainment business was still his first love. Here, he's pictured with Taylor Swift, the aspiring country singer, at her Sunnyvale performance.

I suppose Semel was trying to inject some glamor into Yahoo or prove the company's credentials as a media company. But this photo opportunity, showing Yahoo's boss, arm-wrestling with Tom Cruise, became an unfortunate symbol of a company that had lost its way. The company was being trounced in search, Sunnyvale veterans balked at the expense of Yahoo's Hollywood adventure — and Semel still expected them to be impressed by his superstar buddies.

In 2006, it all began to go wrong. Brad Garlinghouse's Peanut Butter Memorandum showed senior execs had lost confidence in the company's leadership. 63-year-old Semel had been seen as seasoned; increasingly, as he failed to recognize new opportunities such as social networks, he just seemed old.

The loyalists: Semel having sushi with Toby Coppel, long-time lieutenant. This photograph, taken by Bradley Horowitz, Semel's inhouse tech guru, was taken the evening after Yahoo announced the departure of Dan Rosensweig, a sacrifice to assuage the markets. Yahoo's reorgs never went far enough: largely because, for any meaningful effect, Semel would need to terminate himself, first.

At the Christmas party, after Sunnyvale's 2006 reorg, Semel seemed more uncomfortable than ever, and the Yahoos more depressed. Here he is, leaving the premises, surrounded by security guards and his retinue, like a departing dictator.