Andrew Friedman faces a tough decision

Updated: August 21, 2011, 11:41 AM ET
By Buster Olney

Yankees general manager Brian Cashman once aptly compared his work to that of Sisyphus, the king doomed to constantly push a boulder up a hill, only to see it roll back down. Year after year, Cashman and Boston general manager Theo Epstein are now expected to construct teams with the ability to win a championship.

But they have the tools to do it. It's as if the Boston Red Sox and New York Yankees have bulldozers, while Tampa Bay Rays general manager Andrew Friedman is working with a shovel. You couldn't blame him if he began to suffer from American League East fatigue, trying to squeeze production out of every nickel of his payroll, while knowing that the Yankees and Red Sox will always have the wherewithal to paper over mistakes with dollars.

Friedman and those who work with him have probably done their jobs as well or better than any organization in the majors over the past five years, and yet most years, the odds are that Tampa Bay will be exactly where they are today: They are good, but not great enough to keep up with two division rivals that have staggering resources. And no matter how well the Rays develop players and run their finances, they will almost never retain their best players if they reach free agency.

Friedman, then, will have interesting choices this offseason, when he presumably will be offered the opportunity to take over the baseball operations of the Houston Astros, and perhaps the chance to run the Chicago Cubs.

With the Rays, he works among people he has come to know and trust, among people who know and trust him, the kind of work environment that nobody should take for granted. On the other hand, he does his work knowing that he can do everything perfectly within his means -- picking the best available players and maximizing value -- and the Rays may still finish a dozen games out of first place most seasons, well into the future. Because right now, Tampa Bay has roughly the same chance of getting a new ballpark as the U.S. has of balancing its budget. It's not close.

If Friedman goes to Houston, he would be reconstructing the Astros almost from the ground up. If he went to the Cubs, he would be taking on a franchise that hasn't won a championship in more than a century.