It’s Time to Go Halladay Shopping
By Jed Weisberger ~ November 30th, 2009. Filed under: Jed Weisberger, Offseason Speculation.
Coveted Toronto starting pitcher Roy Halladay is on record stating he will not block a trade to the Yankees.
Meanwhile, some in the Boston organization are talking in terms of their club doing all it can to set up such a roadblock.
That leaves us with the unlikely “love triangle’’ of Brian Cashman, Theo Epstein and Alex Anthopoulos. The trio, general managers of the Yankees, Red Sox and Blue Jays, respectively, could become involved in a process with plenty of intrigue.
First you have Anthopoulos, who has the coveted hurler who would like to move on. His question: Do I deal him now, to one of the two elite teams in my division, or do I hold my cards and risk getting nothing for Halladay, 32, later?
For both Cashman and Epstein there is a definite quandary. Both have the prospects to pry Halladay, who will probably want a five-year extenion at C.C. Sabathia money ($23 million). Do the Yankees, as Anthony McCarron of the New York Daily News asked, want to be paying a 34-year-old starter (Sabathia) and 37-year-old starter (Halladay) a combined $46 million in five years?
Epstein has staff ace Josh Beckett, who made $10.5 million in 2009 and gets $12 million for 2010 under a club option that vested because he made at least 28 starts (actually 32) in 2009. He will be 30 in May and a free-agent after next season. Boston also bid over $51 million for Japanese star Daisuke Matsuzaka and have him under contract through 2012 and have just over $103 million invested in him.
Both Cashman and Epstein agree on one matter – pitching wins championships.
In trading with the Yankees, the Blue Jays want any deal to start with catcher Jesus Montero, the Yankees’ top prospect. His bat is big-league ready at 20 – which he became Saturday. Could the Yankees deal him and not hurt their future? Perhaps.
Also in the system is Austin Romine, another catcher who is more advanced defensively than Montero and is thought by scouts to have 20-to 25-home run potential in the majors. He will play at Double-A Trenton in 2010. Francisco Cervelli, superb defensively, but not a power guy, is also around.
The other components in the deal would probably include either Joba Chamberlain or Phil Hughes, along with outfielder Austin Jackson. This is the part that’s tough. Chamberlain might be worth the gamble in a trade, and be helped by a change in scenery. I see Hughes as a solid starter in 2010. The Yankees have no outfielder in their system as major-league ready as Jackson.
From Boston, the Blue Jays are starting by asking for pitcher Clay Buchholz, who has a big-league no-hitter thrown Sept. 1, 2007, and is 12-14 4.91 in parts of three seasons. Others who have been mentioned include Casey Kelly, a terrific athlete whom I saw pitch in the South Atlantic League, where he was 6-1, 1.12 followed by 1-4, 3.09 at Salem of the Carolina League. He also made 40 starts at shortstop with the two Class A teams combined, but all look at the 20-year-old as a pitcher who could possibly reach the majors by late 2010.
Reliever Danny Bard, who has hit 100 mph with his fastball, is also in the conversation, as are other Red Sox names such as former Japanese pitcher Junichi Tazawa, who reached Boston this year, and power-hitting outfielder Josh Reddick, who played in Boston in September.
Boston has regretted dealing some prospects, including shortstop Hanley Ramirez, who went to Florida in the deal for Beckett. The Red Sox, again needing a shortstop, want to reacquire Ramirez and may need to deal prospects for a budding star who was once theirs.
Both the Yankees and Red Sox have the goods to land Halladay. Both have excellent farm systems. Given their other commitments, however, does Halladay fill the bill for either?
We’ll soon find out.

