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Yankee Panky: Halladay or Holliday Shopping?


SI.com’s Jon Heyman has been on just about every local broadcast media outlet and the MLB Network the past two weeks discussing this offseason’s Free Agent class and potential trade market, all the while saying, “Don’t discount the Yankees in any talks about Roy Halladay, Matt Holliday, or anyone else.”

This, of course, is stating the obvious. Remember the story in The Onion in February of 2003, shortly before Spring Training started, with the headline “Yankees Ensure 2003 Pennant by Signing Every Player in Baseball“? With new developments in the Halladay sweepstakes, and the Yankees’ additional need for a left fielder — contingent upon what Brian Cashman decides to do about Hideki Matsui and Johnny Damon — the Haters could be on the march with a similar headline for 2010. As we’ve seen, however, the Yankees don’t care much about public or media perception when payroll is the topic.

Much of why that Onion-type headline could return is a result of last winter, when the Yankees signed three of the top free agents in baseball to $423.5 million worth of contracts. All of them — CC Sabathia, AJ Burnett and Mark Teixeira — contributed to the World Series title, only feeding the thought that the Yankees bought their championship and leveled the small-market teams’ chances of success. That thought would be, and is, incorrect. Cashman didn’t buy a title, he bought the necessary pieces — buying on need as opposed to greed — to put his team in the best position to win. Cashman has said through the years that’s all a general manager can do, and he’s right. Once the ink dries, it’s the players’ jobs to perform and live up to those contracts.

What to do now? Cliff Corcoran has done his usual yeoman’s work analyzing the team’s needs. It just so happens that the two biggest names being rumored to move would fill two of those voids. Let’s take a look at both Halladay and Matt Holliday, since there’s nothing else better to do leading up to the Winter Meetings in Indiana City, Indiana.


Per a Daily News report, Halladay told the Blue Jays Saturday that he would waive his no-trade clause to come to the Yankees, if the pieces of a deal came to fruition. (Read: “I would waive the no-trade clause to go to the Yankees because I know they’re on the short list of teams that don’t need to win the lottery to pay me, and I won’t have to deal with the exchange rate.”) This is super-interesting because a week ago, it looked like the Red Sox were all-in and Yankee fans, some of us still in a championship daze, cried a collective variant of “Uh oh.” ESPN made it worse, posting a projected 2K10 Red Sox rotation of Halladay, Beckett, Lester, Dice-K and Buchholz (not taking into account that Buchholz may be the linchpin in getting or not getting the ’03 Cy Young Award winner).

What it means: Nothing yet. This is still very much in the conjecture phase. As the article states — and we know — the Blue Jays want high-end prospects and young players who are either major-league ready or have some experience. The article also notes how the Yankees did not want to travel down this path two years ago when Johan Santana was the soon-to-be-traded pitcher.

This year is different, as are the pitchers in question and the prospects rumored to be mentioned. The Yankees know Halladay better than they knew Santana. They know his success level against the AL East, particularly against them. Acquiring Halladay would be akin to Roger Clemens, only without the baggage. Secondly, the prospects and young players the Yankees did not want to part with then — Phil Hughes, Ian Kennedy, Joba Chamberlain, and Robinson Canó, to name a few — might be on the list of players Cashman considers dealing now.

Decisions need to be made on all three pitchers, and Canó, as great as he was in the regular season, disappeared in the postseason like Alfonso Soriano did in 2003. But Canó is not the subject of a possible position change and hasn’t complained at all, so if he is traded, it’s purely a business decision and not because he’s partly a malcontent. For what it’s worth, the News calls Jesus Montero and Austin Jackson two of the players the Jays “would require” from the Yankees in exchange for Halladay.

And of course, there’s the matter of budget. Anyone in the Halladay mix is going to have to be able to afford signing him to a three-to-five year extension in the $20 million-per-year range. This is not a light consideration. Remember, the Yankees thought they were hedging a solid bet on Javier Vazquez, signing him to a four-year, $40M extension before the 2004 season only to include him in the Randy Johnson trade the following December.

The caveat to any potential Halladay trade is Vernon Wells, who assuming he doesn’t opt out of his contract, is owed $21 million next season. Nothing like doubling your salary a after a .260/.311/.400 effort. Wells is essentially the 2009 version of what Mike Lowell was for the Marlins in the Josh Beckett trade in 2006, only at a much higher cost.

With all that said, if the Jays view the Yankees as the ideal trading partner and the Brass pays no regard to the checking account, here’s a potential deal:

TO TORONTO: Joba Chamberlain/Phil Hughes, Austin Jackson, Michael Dunn/Phil Coke

TO NEW YORK: Roy Halladay, Vernon Wells

Why? The Yankees need to make a decision on Chamberlain and Hughes. Will they be starters? Relievers? Will one be a starter and the other inherit Mariano Rivera’s closer spot? In Jackson, the Jays would get a young player ready to make the leap, and the Yankees would basically be saying they’re committed to Melky Cabrera being their everyday center fielder, offensive warts and all.


A three-time Silver Slugger winner who has played in relative obscurity his entire career, Matt Holliday’s bat would provide additional right-handed protection in the middle of the lineup behind Alex Rodriguez. It would also allow Joe Girardi to move Canó to the No. 2 hole, where despite his .272/.293/.415 career split hitting from that spot in the order, he has the potential to thrive hitting behind Derek Jeter.

There are two issues with Holliday: the first is his fielding. The teams most likely in the running for Holliday — the Yankees, Red Sox, Cardinals, Giants, and Mets — all have left fields that are either spacious or asymmetrical. The GMs of those teams have to be looking at the ham-handed error he made in Game 2 of the Division Series against the Dodgers and wondering if the amount of runs he creates will outweigh the amount of opponents’ runs to which his defense could contribute.

The second issue is Scott Boras. Numerous reports indicate Boras is likely to ask for a Teixeira-type contract both in years and cash. Is that a deal the Yankees want to make? It could be if they want to get five years younger in left field. It’s a better option than signing Damon to an eight-figure, multi-year deal.

We’ll have more of an idea of where the Yankees lean once the organizational meetings in Tampa wrap at the end of this week.

Even then, though, the safest bet is to not believe anything we read, hear on talk radio or see on TV. As Heyman said, the Yankees will probably be in the discussion for just about every big name available. And so will the Red Sox. Which means that if the Yankees don’t win either of the two big prizes this offseason, the only way fans will be placated is if Boston loses out on both of them also.

Categories:  Bronx Banter  Will Weiss  Yankee Panky

Tags:  Matt Holliday  Roy Halladay

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1 Diane Firstman   ~  Nov 30, 2009 11:24 am

I hope the Yanks see the "True Value" of Halladay and Holliday, so that when I take the "Subway" to the park in 2010, I won't be disappointed. :0

2 Jon Kantrowitz   ~  Nov 30, 2009 11:39 am

Please don't sign any more high-priced long-term contracts except for 26 year old players like Josh Johnson or absolute studs like Joe Mauer. Fans have to look beyond next year and visualize a group of players who need walkers to get to their positions. No Holliday/Halladay please.

3 williamnyy23   ~  Nov 30, 2009 11:40 am

This came up earlier in the off season, but why all the talk about trading Cano? The Yankees need young, talented position players and that's exactly what Cano is. Also, it is not only unfair, but also untrue to say that Cano disappeared in the post season. He did have an .892 OPS in the ALCS with a .414. OBP. As bad as his two other series were, it was nothing like Soriano's. After all, Cano only K'ed 9 times in 3 series compared to Soriano, who struck out an incredible 26 times.

I also don't get why you think a team would need to be able to sign Halladay to an extension. From the reports I have read, he seems more than happy to test free agency, so a Sabathia to the Brewers like arrangement is possible. Furthermore, I don't see why the Yankees would give up two highly touted players AND pick up Wells contract. If any team takes Wells, the Jays will be lucky to get one good prospect.

Finally, Matt Holliday has consistently rated as an above average to very good defensive left fielder. One high profile error doesn't erase that. If teams are really foolish enough to let one play impact their decision than they probably aren't well run in the first place.

4 williamnyy23   ~  Nov 30, 2009 11:42 am

[2] Holliday and Tex are about the same age heading into their free agency periods. The Yankees need to sign talented players, not young ones.

5 sonyahennystutu   ~  Nov 30, 2009 11:53 am

I agree overall with William. We hear all the time that the major hole in our system is a lack of position player bats. In Cano we have a relatively cheap, young, up the middle guy who hits and fields. Yeah yeah I know about the apparent lapses. But overall body of work is very impressive IMO. I can't believe we trade him for anyone not named King Felix.

6 Diane Firstman   ~  Nov 30, 2009 1:00 pm

Free agents are going to tend to be older signees, just due to the definition of having 6+ years in the majors. You aren't going to find many 26-year-old free agents.

7 TheGreenMan   ~  Nov 30, 2009 1:01 pm

Well, I'm gonna disagree with you on a couple of things you wrote about Matt Holliday. He hasn't played in "relative obscurity his entire career". Relative to A-Rod, sure...

But he has been on the big stage of baseball since at least his 2006 season and he had a couple of decent seasons before that including a 5th place finish for RoY in 2004. And his 2007 season was one for the ages including some really big moments in the post-season/playoffs. Then he was involved in two huge trades in under a year that were the talk of the baseball community at the time. West Coast does not equal relative obscurity to baseball fans.

And as for his fielding I don't think that GMs are going to look at one poor play in the OF in the playoffs to judge how effective he might be in the field. They should and they will look at a larger sample size. This past year he was an above average defender in LF coming in 5th in the new Fielding Bible awards for 2009. And his Dewan +/- numbers have generally been positive over his years in the bigs, meaning that he will and has made plays that other LFers might not make.

I don't hold them to be 100% accurate, but some folks smarter than me have come up with metrics that show he can play the field and help his team out while doing it. And his throwing arm, while not anything special, hasn't cost his team any runs over his career. At least according to Retrosheet and others.

8 YankeeAbby   ~  Nov 30, 2009 1:19 pm

In completely unrelated news (or maybe it is related - I'll let y'all decide):


9 51cq24   ~  Nov 30, 2009 1:40 pm

i wouldn't want halladay in boston, but i definitely wouldn't give up what you suggest in order to keep that from happening. as william says in [3] (and others including myself have said since the world series), trading cano would be a terrible mistake. and i think trading either hughes or joba would be one as well. i know people have soured on joba, but i still think he will be an ace. he still hasn't gotten a real chance. and hughes will be a good #2/3.
while you argue the yankees "know" halladay better than they knew santana 2 years ago, i'd hope that cashman isn't stupid enough to value halladay higher than santana just because he's seen him more. santana was not only a better pitcher 2 years ago than halladay is today, he was also 4 years younger. to give up for halladay what we wouldn't give up for santana would be absurd. especially when the 2 pitchers are closer to being able to give us significant innings.
let boston sell the farm for halladay. it would suck, but wouldn't be the end of the world. and maybe it would backfire on them after a year or two.

10 Yankster   ~  Nov 30, 2009 4:55 pm

[3] good points, esp. on Cano.

I don't quite have all the math down but I don't think the Yankees are going to grow payroll. 15.75 for Halladay and 21 for Wells is 36.75 million new next year, while only 13 and 13 are coming off the books. I'm sure they can afford it, but it fails both the fairness smell test and the revenue efficiency test (because of the cap penalty).

Finally, if the jays can get a cost and multi-year controlled front of the rotation starter for Halladay (who they will lose in a year anyway), I think they have to take it, with barely a position player thrown in depending on the starter. I'm not saying Halladay isn't more valuable than that, I'm just saying the Jays don't actually have enough player control here to sell him at market price.

That said, losing hughes or chamberlain for a $16 million 1 year rental is tough to swallow (though I guess he will be a type A free agent after the year, so at least we get a prospect back).

11 Will Weiss   ~  Nov 30, 2009 9:17 pm

[10] ... "Losing hughes or chamberlain for a $16 million 1 year rental is tough to swallow"... which is why the Yankees had better be prepared to sign Halladay to an extension. If the Yankees are going to trade for him, he's not going to be a rental.

[3] ... William, you and the subsequent readers make good points about Cano. Please note that I'm not suggesting the Yankees should or will trade Cano, only that his name could very well come up as one that is included in a deal. And if I'm Brian Cashman, I'd be foolish not to examine every potential trade chip.

[9] I would deal either Joba, Hughes or Kennedy to get a return of Halladay in a heartbeat. Joba more so than Hughes or Kennedy. His future with the Yankees is better suited, as I've said here for two years, as a closer. Hughes is better suited as a starter. ... And you're right about the age difference between Santana and Halladay at the points of their impending trade. However, to say that one is better than the other at this particular stage is really a toss-up. They're different types of pitchers. Santana is a strikeout, power pitcher while Halladay is a power pitcher but has more of a tendency to pitch to contact.

12 Mr. OK Jazz TOKYO   ~  Nov 30, 2009 9:26 pm

A big "NO" to Holliday & Halladay...and to that shockingly depressing shopping center in the photo above..yuck...

13 Will Weiss   ~  Nov 30, 2009 9:41 pm

[12] Leave it to you, Mr. OK Jazz, to always keep it real in a different way than the rest of us do. I'd still take the arm over the bat.

14 Mr. OK Jazz TOKYO   ~  Dec 1, 2009 12:34 am

[13] Hey Will, checking in from 14-hours ahead always creates a skewered perspective :)

Not that the US suburbs have a monopoly on ugly buildings..future architects will look back at 20th century Japan as the "grey concrete box" era...behold...


15 Mr. OK Jazz TOKYO   ~  Dec 1, 2009 12:36 am

oops..this one!


16 Will Weiss   ~  Dec 1, 2009 9:00 am

[15] Throw a drum kit in any of them and it's suddenly beautiful.

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