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Whether or not Fielder is a guy to bet the farm on is Jack's call. The problem is that even if he IS such a guy, if Jack went to Lincoln/Armstrong about pursuing him, they would back out as soon as market value came into play. It would be "too risky" for their bean-counter comfort.
http://www.theargonath.cc/characters/gollum/sounds/rotk7.wav
They're ownership. They have the right to make that call. They also have the right to be a lousy team year after year while asking the fans to keep coming through the turnstiles.