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Yankee Panky: Halladay or Holliday Shopping?

Posted By Will Weiss On November 30, 2009 @ 10:59 am In Bronx Banter,Will Weiss,Yankee Panky | Comments Disabled


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 [1]“? 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 [2], 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.

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URLs in this post:

[1] Yankees Ensure 2003 Pennant by Signing Every Player in Baseball: http://www.theonion.com/content/node/27656

[2] Daily News report: http://www.nydailynews.com/sports/baseball/yankees/2009/11/29/2009-11-29_halladay_shopping_in_swing.html

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