It looks like Howry and Millwood aren't really close with the Tribe at this point. Millwood is the key here, he really helped this team. If the Indians offer him a fair/market value deal, then I am content. They can't over spend for him, they just can't.
With Howry its a bit different, his status depends on Wickman. If Wickman retires, then Howry becomes much more important. If Wickman decides to stay, then paying a ton for Howry doesn't make sense. In a perfect world, the Indians could sign both these guys and find a way to trade for Manny.