The Yankees' case for Halladay

The Yankees, Mets and Red Sox have spent more money in free agency over the past decade than any other teams, as ESPN's esteemed Mark Simon notes:

Biggest free-agent outlays 1999 to 2008 (approximate in millions)

Yankees: $1.45 billion

Mets: $651.3 million

Red Sox: $621.0 million

Cubs: $598.4 million

Giants: $595.2 million

Smallest free-agent outlays 1999 to 2008 (approximate in millions)

Pirates: $55.6 million

Twins: $80.2 million

Athletics: $87.7 million

Nationals: $91.5 million

Padres: $106.1 million

But then again, you knew that already. Even in years in which free-agent outlay is diminished by a high percentage -- and this is probably going to be one of those years -- the Yankees, Mets and Red Sox are usually pretty active, relative to teams like the Pirates. To put the above numbers in perspective: Mark Teixeira and CC Sabathia will make more in free-agent dollars in the first three years of their current contracts than the Pirates have spent in the past decade ... on anybody.

There will be more of the same this offseason. The Yankees won't necessarily be the winning bidder on John Lackey, Matt Holliday or Jason Bay, and they do intend to try to lower their payroll. But they do have what many, many teams don't have: the financial capability to paint outside the lines and pursue a player who makes them better, despite the cost.

Which brings us to Roy Halladay.

Two winters ago, the Yankees essentially passed on the opportunity to trade for Johan Santana because they were unwilling to absorb the double-barreled cost of first trading prospects like Phil Hughes or Joba Chamberlain, and then paying Santana like a free agent. The Yankees have been vindicated for that choice. They kept Hughes, Chamberlain, Melky Cabrera, Austin Jackson and all the other prospects discussed as possible pieces in a Santana deal and saved their money to sign CC Sabathia, and as a result they will now spend part of this winter asking club employees for their ring sizes.

Now Halladay is available, and there are many parallels between the Halladay and Santana situations. The Yankees (and Red Sox) are generally leery of giving up their best prospects and throwing in a long-term contract for Halladay, who turns 33 next season and has pitched a lot of innings.

But here are a couple of things that are different since the Santana talks: Hughes and Chamberlain. They are two years older, two years further along, with (generally) two more years of major league service time. Both players will be eligible for salary arbitration for the first time after next season. Hughes, 23, is coming off a year in which he demonstrated that he could be a shut-down reliever during the regular season -- he struck out 96 in 86 innings, with a 3.04 ERA -- before he struggled in October. Chamberlain, 24, had flashes of excellence as a starter, but generally was erratic, before finishing his year with some strong outings in the postseason.

If I were sitting in Brian Cashman's chair, I would identify the smartest pitching people I have on my staff, whether it be manager Joe Girardi or pitching coach Dave Eiland or others, and I would ask them two questions: What are Hughes and Chamberlain now, and what do you think they will be going into the future?

In other words, do you think in three years they will be middle relievers? Do you think they will be dominant closers? Do you think they will settle in as back-of-the-rotation starters, or do you think they will be frontline AL East starters?

And if the smart people that Cashman trusts believe that Hughes and/or Chamberlain will be anything other than (A) dominant closers, or (B) No. 2-type AL East starters, well, then I'd call Toronto immediately and be ready to talk about trading one or perhaps even both of the young pitchers.

In the midst of Boston's trade discussions about Santana, Red Sox pitching coach John Farrell all but threw his body in front of young left-hander Jon Lester, who had pitched a total of 144.1 innings in the big leagues at that point. Farrell argued that the Red Sox should keep Lester and not trade him for Santana, stating that the lefty could wind up winning more games than Santana over the course of Santana's contract. And Farrell has looked pretty smart so far: Lester has won 31 games over the past two seasons, Santana 29.

You can bet that Girardi and Eiland, who have strong opinions, have clear-eyed views of what they think Chamberlain and Hughes can become.

Some of the best rival scouts have doubts about whether Chamberlain will be able to maintain and repeat his delivery -- the source of his inconsistent control in 2009 -- as he gets older, and there are growing concerns about whether Chamberlain could be anything more than a five-inning starter. Some of the same scouts do think Chamberlain is capable of being an effective late-inning reliever. Do Eiland and Girardi, who know Chamberlain better than anyone, share those sentiments? Do they see more in him? Some of the best rival scouts were greatly impressed by Hughes's improvement last year, and they see room for growth in him, but they wonder if he'll ever be a frontline starting pitcher, given that he generally pitches at 90-91 mph. They wonder if he'll develop a strong third pitch, which would be necessary for him to evolve into a top starting pitcher. Do Eiland and Girardi see him that way?

If Girardi and Eiland see great futures for the two pitchers, Cashman should keep them. But if Girardi and Eiland project either or both as above-average middle relievers, or as average starting pitchers, then the time is now for Cashman to look to trade them, to capitalize on their value, and to build a package in an attempt to get Halladay. Because the Yankees, with their resources, should never have any trouble acquiring average starting pitchers or above-average relievers.

Cashman has been right to focus on the team's player development over the past four years, and Chamberlain and Hughes are two of the jewels from the Yankees' system. But if the Yankees believe internally that either is not going to reach the excellence projected for them in 2007, then they should make their move now, while one of the best pitchers on the planet is available.

Across town

The Mets are coming off a brutal season, and they may or may not become serious bidders for the big three of John Lackey, Matt Holliday and Jason Bay. But at the very least, they appear to be well-positioned to grab the best of the B-listers: the second-level veterans. "A few years ago, there weren't many teams that were capable of spending $12 million to $13 million a year on a player," said one executive. "Now there aren't a lot of teams bidding for the guys at $5 million, $6 million, $7 million a year."

The Mets can and will do that, and they appear prepared to land two or three solid veterans in that price range.

After Lackey, there is a buffet of starting pitchers who have shown the capability of being pretty good: Randy Wolf, Jason Marquis, Joel Pineiro. It would be a surprise if the Mets didn't land one of those three starters, or somebody comparable.

There is pretty good list of available corner outfielders, and the Mets have discussed Mike Cameron -- who indicated last week that he could be willing to consider a shift to the corner outfield under the right circumstances -- and Xavier Nady and others. The Mets should get a good outfielder. They should get a good first baseman, if they spend $5-7 million. There are a lot of choices available, and there will be more, as some players are not tendered contracts. The Mets, and the Yankees, will again be among the more proactive teams.

Elsewhere, people are discussing this too: No matter where Halladay goes, Joe Girardi says, he will make a significant impact. The Yankees will start some meetings today. Girardi has an early sense that Andy Pettitte wants to pitch next year, writes Erik Boland. A Halladay deal is going to happen before spring training, writes Richard Griffin.

(A footnote from Mr. Simon on the numbers at the top of the column: They do not factor in voidable years, vesting years, options, minor league contracts that became major league deals; we don't have the capability to do that. It also doesn't factor in that a player could have been traded in mid-deal. In other words, we list A.J. Burnett's signing as five years for $55 million with the Jays, when we know he voided the end of the deal. Basically, this is a sum of what was signed at the time, rather than what the team necessarily paid, so it's more estimate than exact figure.)

Moves, deals and decisions

1. The Players Association seemingly would support a seven-game playoff in the Division Series. Michael Weiner, the new head of the union, was the primary voice on the conference call, and as he noted, the Players Association has been around since 1966 and there have been only three different people at the helm before him: Marvin Miller, Kenneth Moffett (briefly) and Don Fehr. These are Weiner's first days on the job, officially, and as he spoke on the conference call, the players who are part of the executive board were in the room. Weiner spoke emphatically -- strongly -- in answering questions from the media, and maybe there was a part of him that wanted to make a solid first impression for the players. Who wouldn't? He has big shoes to fill, and he knows it.

There is a perception within the game, among some executives, agents and older players, that as the union members become more affluent, the union itself is gradually losing the powerful will that has been such a weapon for decades. Whether or not that is actually the case cannot be known, because the Players Association really hasn't had need to forcefully shove back in more than a decade. At one point, Weiner noted that in the past, "the resolve" of the players has been underestimated by some owners, and now, nobody should make the same mistake. Undoubtedly, the owners will push to slice off as much of the practical power as they can, bit by bit -- it's a negotiation, after all -- and it will be interesting to see how cemented the union's positions are in the next round of collective bargaining on issues of revenue sharing, payroll ceilings and floors, and draft slotting.

2. As colleague Jayson Stark reports, the Phillies are targeting Placido Polanco to play third base, and if they sign him, it'll be interesting to see where they hit him in their lineup. Seventh, behind Raul Ibanez? Second, behind Jimmy Rollins, with the more powerful Shane Victorino (62 extra-base hits last year) sliding to the middle of the order? My guess would be that they would hit Polanco eighth, and Carlos Ruiz seventh, given Polanco's on-base percentage. By pursuing Polanco, the Phillies are placing a high priority on defense, for sure.

3. The Reds' roster might look very much like it does now when spring training begins, says Walt Jocketty.

4. The Padres hired an assistant GM out of Boston's front office, as Michael Silverman writes.

5. The Pirates are considering a wide range of pitching options, writes Dejan Kovacevic.

6. Boston's decision to acquire Billy Wagner for the stretch drive is paying off in a big way, now that the Red Sox (as of today) would get the Braves' first-round pick. They could sacrifice a draft pick if they sign a Type A free agent, such as Marco Scutaro, and Scutaro is a strong possibility for the Red Sox, writes Joe McDonald.

7. The Royals are not shopping Alberto Callaspo, says Dayton Moore.

8. The Indians signed some veterans to minor league deals, writes Paul Hoynes.

9. Kelly Shoppach is capable of being an every-day player for the Rays, Indians GM Mark Shapiro tells Marc Topkin.

10. The bidding for the Rangers continues, writes Jeff Wilson. If Dennis Gilbert does wind up controlling the team -- I wrote here early in the fall that some folks in Major League Baseball would be thrilled if he won the process -- it'll be interesting to see what role Nolan Ryan will play, if any. Ryan has allied himself with Chuck Greenberg, who is bidding against Gilbert, and it's hard to see how Gilbert could be expected to keep Ryan after the way this has played out.

11. Heard this: The White Sox don't have a lot of payroll flexibility this winter, which is hardly surprising after a summer in which they took on over $100 million in salary obligation with the acquisition of Jake Peavy and Alex Rios. Kenny Williams isn't being aggressive in the free-agent market, writes Mark Gonzales.

12. Says one high-ranking executive: "If Rafael Soriano turns down arbitration, he's insane." The Braves offered Soriano arbitration, and the right-hander could make about $8 million through the process, or more than Billy Wagner will make to be the Atlanta closer.

13. Heard this: Some agents for the players who were offered arbitration are aggressively calling around looking for better offers for their clients from other teams. One executive said: "I think a lot of the agents are looking at what happened last year with [Jon] Garland and [Jason] Varitek" -- who both turned down arbitration offers, and wound up taking much less in contracts than they would have gotten through arbitration -- "and they don't want to make the same mistake."

14. Looks like Jose Contreras could be going to Japan, writes Troy Renck.

Dings and dents

The Padres' No. 1 pick, Donavan Tate, was injured in an ATV accident. Not good.

Other stuff

• John Shea asks the question: Who profits from revenue sharing?

• Dave Dombrowski's tenure as Detroit GM has been a bumpy ride, writes Tony Paul. His faith can be his biggest flaw, writes Paul.

• It's not a big deal if the Astros lose Miguel Tejada, Jose Valverde and LaTroy Hawkins, writes Richard Justice.

• Topps has completed an exclusive deal with Major League Baseball, as Tim Lemke writes.

• Dan Connolly says he would vote for Roberto Alomar for the Hall of Fame.

• The Padres hired Dick Enberg.

• Vanderbilt is off to a great start.