5. Alexei Yashin
Yashin had a great career with the Ottawa Senators before his relationship with the franchise collapsed. He believed that his contract allowed him to void the final year and become a free agent. However, the Senators disputed this and refused to release him. This created an impasse between the player and the franchise. But it continued to escalate (via The Globe And Mail).

The Russian sat out for the entire 1999-2000 season because he thought this would guarantee free agency. But Ottawa brought him to court and claimed he failed to meet the terms of his contract. The court of arbitration agreed and Yashin found himself back on the ice with the Senators. The fans didn’t give him a warm welcome but he had a decent final year in Canada.