I've been against the Yankees trading for Roy Halladay since he became available on the trade market. It really has nothing to do with Halladay himself - clearly, he is one of the best half-dozen pitchers in the game - but everything to do with the costs of acquiring him, not only in prospects, but also in salary. The Yankees have huge financial resources at their disposal, but they already have $95 million dollars of payroll - $95 million! - committed for the 2013 season, and that doesn't include Derek Jeter's inevitable contract extension. I don't care if we're talking about Roy Halladay, Albert Pujols, or Babe Ruth's ghost, I just think it's unwise to make another huge financial commitment through the middle of the next decade to another player who will be on the wrong side of 35 when the contract expires.
Putting those concerns aside, I don't like dealing for Halladay simply because it's too obvious and too predictable.
The thing that separates good teams and good GMs from mediocre ones is the ability to get creative and to think outside the box, to get something for nothing, or something for very little. Think about it. Signing Matt Holliday or Jason Bay, or trading for Roy Halladay or Felix Hernandez, doesn't really take much. Sure, GMs need to be able to pony up the money or the prospects, or both, to make these guys a part of their team, but it doesn't require much thought.
I want to see the Yankees make the non-obvious move and get $20 million of production for $15 million, or trade a handful of B-list prospects for a solid contributor. I want to see Cashman make more moves like the trade for Dave Justice or Nick Swisher. I want to see him get a deal or find a bargain.
This is how the Yankees starting rotation broke down, in terms of WIns Above Replacement, in 2009:
1. C.C. Sabathia - 5.3 WARP
2. A.J. Burnett - 3.2 WARP
3. Andy Pettitte - 2.4 WARP
4. Joba Chamberlain - 1.0 WARP
5. Wang/Mitre/Gaudin/Hughes - -1.7 WARP
Halladay has averaged 5.5 WARP over the past five seasons, so if you plugged him into the Yankees rotation, he'd replace the Wang/Mitre combo and would theoretically represent a net 7.2 win upgrade. That's huge. But it's not the only way to improve the rotation.
Suppose Joba posts 2.0 WARP from the 4th slot and Hughes manages 1.0 WARP from the 5th - that's a 3.7 win upgrade. Or suppose the Yankees sign Ben Sheets and he puts up a 3.0 WARP season - that's a 4.7 win upgrade. Let's even think about Chien-Ming Wang returning to form and posting another 5.0 WARP season like he did in 2007 - that would represent a 6.7 win upgrade. Even something as simple as getting replacement-level performance from the fifth spot improves the team by nearly two wins.
And so my point is that while adding Halladay is obviously the best way to improve the rotation for 2010, if Cashman could add 50-75% of that production for 10% of the cost, shouldn't he do that instead?