The Chicago Cubs organization has made its fair share of questionable roster decisions in the past.
There have been mind-boggling trades and head-scratching free agent signings to go along with decisions to not re-sign talented players.
One of the many proclamations Theo Epstein and Jed Hoyer have made since coming to the North Side is their intention to not offer any more contracts with a no-trade clause. Ryan Dempster and Alfonso Soriano would be relevant examples why, but they both were 5/10 players.
The reason for not offering no-trade clauses is to avoid having player contracts hinder the club’s plans at any future point.
Not all team-detrimental contracts have a no-trade clause, however. Some are for six, seven, or eight years; or both long and no-trade. Then there are some contracts that are for only one or two years and also shoot an organization in the foot.
But bad contracts are not the only way a club can get in the way of their own future.
There are trades that leave you wondering if the owner or general manager was liquored up when they made the move.
Then there are decisions to let a player pursue free agency when the organization believes he's past his prime—Boston Red Sox/Roger Clemens, 1996.
This list is a review of the top ten worst roster moves in Chicago Cubs history. (Watch for a future article profiling the top ten best roster moves in club history.)