Work A Trade & Sign
Say what? This isn't the NBA! Besides didn't you just say that odds were long that Choo would sign an extension anywhere? Yes, I know this isn't the NBA and yes I did say that the odds were long....but not impossible. Trade and sign deals don't happen often in major league baseball but they do happen and should be explored as history shows benefits can be advantageous for the Indians.
The player was Joe Carter and then Indians GM Hank Peters wanted desperately to sign him to a long term contract. He made several proposals to Carter's agent Jim Turner and each one was rejected and Turner made at least one counter proposal which Peters rejected. After the 1989 season Peters made one last offer to Carter for 3 years at $10M and after Carter rejected the offer Peters released a statement to the press announcing that the negotiations had ended and Carter would be traded by the end of the year.
Since Carter, like Choo, was entering the final year of his contract the team acquiring him would want to sign him to a long term extension before finalizing the deal with the Indians. This didn't seem to be much of a deterrent until Turner alerted Peters that Carter would only sign extension with 5 teams (Padres, Dodgers, Angels, Royals, or Cardinals).
Luckily, Jack McKeon was running the Padres who had finished 2nd to the Dodgers in 1989 a mere 3 games behind the San Francisco Giants and had a loaded farm system. The Indians and Padres reached a deal that would send Carter to the Padres in exchange for Sandy Alomar Jr., Chris James, and Carlos Baerga and the next day the Padres and Carter reached an agreement on a 3-year $9.2M contract. The trade became official on December 6, 1989.