Who

Appropriately named Cashman has the enviable job of picking players for the Yankees, and the unenviable job of answering to the capricious Steinbrenner family.

Backstory

Cashman grew up in Lexington, Kentucky, where his father, a horse trainer, got to know George Steinbrenner, a fellow race horse enthusiast. During the summer of 1986, Cashman started with the team as a college intern; after graduation, he was hired full-time, moving up to the position of assistant general manager in 1992. In 1998, at just 30, he became general manager and senior vice president.

Cashman's appointment as GM coincided with the start of the Yankees' golden years—they nabbed three straight championships from 1998 to 2000 and reached the World Series again in 2001 and 2003. Much of the success, of course, stems from having the largest payroll in baseball, which has enabled the team to lock in some of the best talent around. But Cashman's also earned credit for his financial savvy. It was his idea, for example, to move many Yankees home games to 7:05pm from 7:30pm to maximize concessions sales.

Of note

With great payroll comes great responsibility, and the Yanks' championship drought since 2000 has led to chronic rumors that Cashman's head may be on the chopping block. He's been criticized for shelling out big money to superstars (Alex Rodriguez, Gary Sheffield, Randy Johnson) with little thought of team chemistry, and he's has had particular difficulty assembling a pitching staff. A number of big-money free agent pitchers have been flops for the team, notably Carl Pavano, who signed a four-year, $40 million deal in 2004 but whose Yankees career appears over after a series of injuries; also derided was Cashman's 2007 decision to sign 44-year-old free agent Roger Clemens to a one-year contract that paid him nearly $20 million for about two-thirds of a season of work.

After the disappointing 2007 season, Cashman narrowly avoided his own ouster but sanctioned that of Joe Torre; the former's fate going forward is now largely tied to that of the man he selected to replace Torre, Joe Girardi. In 2005, Cashman signed a three-year, $15 million extension, which guarantees him a job through the 2008 season. Whether he comes back in 2009 remains to be seen.

Soundbite

George Steinbrenner remarked to Cashman during a 2005 playoff game: "You're horseshit, and you're overpaid! No one will take your contract off my hands. Maybe the Mets will take you. You have permission to talk to the Mets!"

Personal

Cashman and his wife Mary have a daughter, Grace, and a young son, Teddy. They live in Darien, in a house that features a massive fish tank occupying an entire room. It's serviced weekly by a team of fish tank professionals.

True story

As Yankee fans might guess, working for Steinbrenner has taken its toll on the whole family. Mary Cashman says her husband grinds his teeth so hard in his sleep that it scares her.