Towers: throws strikes! Wow. It isn't hard to find pitchers who can be a #5 and who don't walk an inordinate number of batters. Next.
I like this idea, but probably not for Ellsbury/Bowden. Willis doesn't have anywhere near the dominant presence that Beckett had when the Sox traded HanRam and AniSanch. The Sox got Beckett, Lowell and Mota for 3 minor leaguers. Ellsbury/Bowden would be too much to give for Willis. I DO like the idea of Willis though, certainly as a potential #4 or #5.
His value would be high because the White Sox know what the Sox are going through and will make sure they pay. I'm uncomfortable trading any serious talent into the AL Central. Those teams all have solid bases (Detroit, Cleveland, White Sox, Twins) and make me nervous. He would be a nice acquisition too, but I think because his name is in that middle-to-upper tier of pitchers he would cost too much.
Couldn't the same thing be said about Schilling (who was more dominant than Contreras even dreamt of being) and Wakefield? I would think that any pitcher who suddenly returns to dominance would be worthwhile.
So... a non-issue then...
Doubtful that he's available or worth the cost.
So... probably a no
I would be happy if the Sox picked up Arroyo again. It isn't going to happen, but I wouldn't be mad.
You give a solid reason why all of these guys would be bad acquisitions, while making the argument that they are 'options' the Sox can explore. This team isn't hurting for average starting pitchers. Schilling and Wakefield are average when they are being inconsistent, above average when pitching well. Dice and Beckett are solid pitchers who can help the team win each time out.
Priorities on this team should be to add some legitimate HR power either to the lineup or the bench. Pitching should be 2nd.