The beard would have to go.
Ryan Dempster has been enigma during his 15-year career. At times, he's been one of the league's top hurlers, but at others nothing more than a replacement-level pitcher.
This season is turning out to be one of his best. Dempster has thrown 74 innings over 11 starts (2.31 ERA, 56 H, 63 K, 20 BB) for the horrendous Cubs. Speculation is that the Cubs will look to trade him considering this is Dempster's walk year and the state of their team (20-40, 12.5 games back). Should the Yankees go after the 35-year-old RHP? How much would it take to land him? Who would be bumped from the starting rotation?
Let's start with the last question. At this point, it certainly seems that Ivan Nova would be the odd man out (last night's start notwithstanding). It's not that he's pitched poorly, but there just aren't any weak spots. It obviously won't be CC Sabathia. Phil Hughes has higher upside and has performed better this season. You're definitely not removing Andy Pettitte, who leads the staff in ERA, WHIP and K/BB. Hiroki Kuroda has pitched admirably, seeming to alternate between gems and blow-ups, but has shown a not infrequent ability to dominate. So unfortunately for Ivan, he'd probably have to return to Triple-A in order to get his innings in.
The question of "should the Yankees trade for him?" has a lot to do with the next question, "what would it take to land him?" It would sure be nice to add Dempster, who aside from being durable (at least 31 starts each of the past four years), is showing an ability to reduce hits (6.2/9) and miss bats (7.7/9) this season. Despite a lower than normal BABIP (.243), his FIP (3.25) and xFIP (3.54) are still solid.
He is currently the Cubs best pitcher, and GM Theo Epstein knows his stuff, so he'll be sure to maximize any return for his prized pitcher. We could be talking about two of Manny Banuelos, Dellin Betances, Mason Williams, Tyler Austin and Gary Sanchez (depending on how much, if any, of Dempster's contract they pick up). That's a hefty price considering Dempster's checkered past.
Of course, there's also Matt Garza...