I'm sure everyone is as tired of the Ryan Dempster Saga as I am, but all along I had been assuming offering him arbitration at the end of the season was a no-brainer for the Cubs. If they can't get at least something decent in return, they could offer arbitration and would receive a supplemental pick in next year's draft if he declined. I had also assumed Dempster would decline, which would then net them the pick next year. More importantly than the pick, it would give the Cubs some additional money to play with in the draft to spend how they saw fit.
While I assumed Dempster would decline the arbitration because a bigger deal would be available, the possibility of declining it wasn't a bad situation to be in. The Cubs would get Dempster under contract for about $12 million or so. He's worth that and depending on the value of the win, he's probably more than worth $12 million next season. There was no risk in offering him arbitration so it was a no-brainer.
Upon further thought, I no longer believe the Cubs will offer arbitration. The Cubs won't be contending next year, but it's not like they have a lot of pitching talent to take the ball every 5th day. That was one reason why I figured they'd be fine with him accepting the deal. However, the Cubs will find themselves in this very same situation this time next year.
Dempster, if he returned next year, would maintain his 10 and 5 rights, which allows him to veto any trade. Since the Cubs won't be contending, they would undoubtedly be looking to shop him at the deadline and having had troubles with the process once before, the Cubs are highly unlikely to put themselves in the same situation a year from now. This leaves only one option: trading him.
The more I've thought about this, I believe that was the only option from the start, which further decreased any leverage the Cubs had. I don't believe the Cubs ever intended to offer arbitration. It's not because Dempster isn't worth it. He probably is. It's because they want the prospect or two they can acquire for him and they have no need for him at this point. I think I've been wrong all along to assume they'd offer arbitration.
The Cubs will work out a deal prior to the July 31st deadline because if they don't trade him, they get nothing in return.