The best moves are sometimes the ones you don't make. I my opinion, one of the good no-moves of Yankees GM Brian Cashman was not trading for Johan Santana (and I think highly of Johan Santana, one of the best there is).
Likewise, I hope the Yankees only show interest in Halladay in order to drive the price up for BoSox. To land him they would first have to let go one of the young pitchers in which they still have high expectations—Joba Chamerblain or Phil Hughes—and at least one of the top prospects, Jesus Montero or Austin Jackson.
If they trade for Roy Halladay they will still have to treat him like a free agent when it comes to money—and even the Yankees have to spend it wisely, albeit they have more of them than the other teams—he will demand a contract in the CC-realm. Let us estimate $20 million/year.
Now, there is Lackey—not Halladay-calibre, but definitely one of the 20 best starting pitchers in MLB. Maybe he will get as much as $15 million/year?
How do the two compare? As a ERA+ fan, I look solely at that one stat (a low ERA, measured in ERA+ is all I want from a pitcher, if the team gets that the offense should take of the wins);
Halladay is much better than Lackey. His ERA compared to Lackey's is like Lackey's compare to the average pitchers. But is he worth $5 million/year - and say Joba and Jackson, plus some other prospect?
There is one thing that I really don't like about the deal. The rave of this year's World Series title was The Core Four - without the core, what are we left with? Who will be the core four (or whatever number in 2019?). Robinson Cano and Melky Cabrera, Joba and Jackson, CC Sabathia? There has to be a soul in a team, something to connect to. And building on your own talent, having that as a base to add free-agents to, saves the soul of the team.
Halladay is too expensive, particullary in talent lost, and too old. Lackey appear to be a better option since the talent stays, but he is also expensive.
Now, let me propose a different path altogheter.
What about a platoon of talented pitchers that have been out of it for a while? What if the Yankees gave four highly, talented, experienced, pitchers that have been out with injuries, low base salaries (2M - 4M), with high incentives, both in money and promise of longer contract if they reach a certain number of innings (and of course the lure of a certain, special ring - big and gaudy, but with a high sentimental value)?
There are four such pitchers on the free agent market;
Rich Harden - ERA+ 131 (211 in 2008) - salary 09 - $7 million
Eric Bedard - ERA+ 121 (146 in 2007) - salary 09 - $7.5 million
Ben Sheets - ERA+ 115 (136 in 2008) - salary 09 - $12 million
Chien-Ming Wang - ERA+ 107 (122 in 2007) - salary 09 - $5 million
If two of them return to former standards (and thereby make, say $10 million) the rotation is starting to look very good. Harden has an enourmos potential, and Bedard is not far behind. Sheets has four all-stars appearances in 8 seasons, and had a very good 2008 season. Wang is a potential "core" of the future, having played his entire career in NY, and has a knack for getting wins.
The risk is somewhat high of course, and they might have to go on a Mitre/Gaudin roll again. I don't know, I might be insane to propose it, and we will probably never find out if it was a good idea (unless Cashman reads this and buys the idea).
If not the risk idea, I am at least convinced Lackey is a better option than Halladay— not as a pitcher, but as a deal.
What do you think—am I way off?