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The other thing that may be a bit messy is if Dempster is traded with the stipulation (under the table) that he'd come back to the Cubs afterwards. That way the Cubs can get their cake and eat it too. They get whatever comes back in trade, then Dempster can come back as a free agent without penalty of draft pick forfeiture.
If Dempster is offered arb and refuses (assuming he stays a Cub) then the Cubs can get draft picks since I believe he'd get a better overall deal from another team than what the Cubs would offer him. If he accepts, then the Cubs are still okay because they probably can still negotiate a team friendly deal. This has been discussed in other forums as well by folks smarter than I.
If Dempster is offered arb and refuses (assuming he stays a Cub) then the Cubs can get draft picks since I believe he'd get a better overall deal from another team than what the Cubs would offer him. If he accepts, then the Cubs are still okay because they probably can still negotiate a team friendly deal. This has been discussed in other forums as well by folks smarter than I.