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No way the Red Sox take a Halladay

Posted by Tony Massarotti, Globe Staff  July 9, 2009 11:01 AM

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With regard to Roy Halladay, to paraphrase former Sox general manager Lou Gorman, the question is obvious:

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Where in the name of Willie McGee would they put him?

Four games from the All-Star break and 22 days from the July 31 trading deadline, the Red Sox are now 51-33 in the wake of last night’s 5-4 win over the Oakland A’s at Fenway Park. With a victory over the Kansas City Royals tonight, the Sox could climb to a season-high 19 games over .500. The Red Sox may have the deepest pitching staff in team history, last night’s win giving No. 4 starter Tim Wakefield more victories than any other pitcher in the American League.

By now, you know that Toronto general manager J.P. Ricciardi indicated earlier this week that he would entertain trade discussions on ace Roy Halladay, who has more wins than any pitcher in baseball since the start of the 2002 season to go also with the best winning percentage (.707). Since the start of the 2006 campaign, Halladay has more complete games (23) than any pitcher in baseball and has thrown more innings (807 1/3) than anyone but CC Sabathia (808 1/3). Halladay has one career Cy Young Award (2003) and has finished in the top five of the voting on four occasions.

His appeal is obvious, and if the Red Sox wanted to make a deal for Halladay today, they could.

But they won’t.

Let’s start this discussion with an obvious truth: Because of the depth of their farm system, their financial resources, and their status as the most successful team in baseball this millennium, the Red Sox can trade for just about any player they want. It is a question of how much they want to give up. No team in baseball currently can match the Red Sox’ combination of financial wealth and minor-league talent, which is a credit to the team’s baseball operation. Any time a marquee player becomes available, the Red Sox are part of the discussion.

Even when, as now, they have far greater needs (read: a hitter) than pitching.

As of late yesterday, the Sox had yet to inquire with the Jays about the price for Halladay. Two days ago, a baseball source indicated that Toronto officials would be shocked if the Sox met their demands for the player. Everyone in the game knows that the Sox love their prospects and their farm system, and they also know that the Sox are built for the long haul as a result of it.

Really, haven’t we been here before? Nearly two years ago, after the Sox won the 2007 World Series, Halladay was available, too, in a sense. The only difference was that his name was actually Johan Santana. The Sox engaged in discussions with the Minnesota Twins -- just enough, but not too much -- to jack the price for Santana’s suitors. In the process, the Sox were either going to keep Santana from going to the Yankees entirely or ensure that New York sacrificed its primary pitching prospects in order to get him.

In the end, Santana went to the Mets. By late October of last year, neither New York team had qualified for the postseason while the Red Sox came within one win of a third World Series appearance in five years.

In the short term, there is no question that Halladay could dramatically impact the balance of power in any playoff race. He is that good. According to one modern media item out of St. Louis today -- OK, it was a tweet from longtime baseball reporter Joe Strauss -- one Cards official suggested the team would be willing to let the Jays pick any five players from their minor league system for Halladay. While that may be construed as nothing more than hyperbole, consider that aces like Bartolo Colon (from Cleveland to Montreal in 2002 for Grady Sizemore, Cliff Lee, and Brandon Phillips) and Santana have commanded as many as three or four top-level prospects. Using that as an outline, the cost for the Red Sox would be a package that might include a combination of at least three players from the group of Clay Buchholz, Daniel Bard, Michael Bowden, Casey Kelly, and Lars Anderson, among others.

Some of us (guesses anyone?) would be more than willing to make a trade like that. To this point in his career, Epstein has all but formally identified those folks as fools.

If, indeed, the past is prelude, ask yourself this: What top-level prospect has Epstein ever traded? Freddy Sanchez was a Dan Duquette draft pick who went in the Jeff Suppan deal in 2003 -- and Epstein still regrets that one. David Murphy? The Red Sox saw him as an extra outfielder stacked behind, among others, Jacoby Ellsbury. Hanley Ramirez might still with the club if Epstein had not resigned following the 2005 season. Craig Hansen had long since become a bust when he went in the Jason Bay deal.

Meanwhile, the Red Sox have drafted and developed Ellsbury, Jon Lester, Dustin Pedroia, Jonathan Papelbon, and Justin Masterson, to name a few. For all of the talk in recent years about how the Patriots have rarely been hurt by a player they elected to cut free, the same effectively could be said for the Red Sox with regard to their young players.

In the case of Halladay, in particular, there is a great deal to consider. At the moment, he is signed only for this year ($14.25 million salary) and next year ($15.75). With free agency looming, any kind of extension for him would fall in the territory of Sabathia and Santana, each of whom is making in the vicinity of $23 million a year. Then there is the matter of his age. Halladay will turn 33 at the start of next season, and the Sox typically have avoided making any type of major investment in pitchers in their 30s.

Again, let’s look at the past. When the Red Sox signed Lester, Beckett, and Daisuke Matzuaka to long-term deals, all of those players were in their mid-20s. As part of the trade negotiations, Curt Schilling got a two-year extension. Ever since signing Matt Clement to a three-year, $25.5 million deal that proved to be a flop -- even that might not be regarded as a major investment -- Epstein has spent more time investing in one- or two-year projects like John Smoltz, David Wells, Brad Penny, and Wade Miller (remember him?) than in anyone who would command a great percentage of the payroll.

The bottom line is that a guy like Halladay represents everything Epstein would run from because he would require both the forfeiture of significant talent and a colossal financial investment. That’s a lot of risk.

During their time as the operators of the Red Sox, Epstein and his staff have had their share of luck, too. They tried to give away Manny Ramirez and failed. Then they nearly acquired Alex Rodriguez. They had David Ortiz behind Jeremy Giambi, for goodness sake, and pursued, among others, Carl Pavano and Jose Contreras. Again, Epstein probably wouldn’t have made the Beckett deal, though he did sign him to a new contract.

If any or all those things break differently, we might look at the Red Sox far more differently today.

Nonetheless, the Red Sox are where they are today because of good talent and shrewd management, not necessarily in that order. No one player is valued too greatly. A productive farm system is clearly the best way to make consistent runs at championships. Augmented with free agency and trade acquisitions -- and not the other way around -- the Red Sox should be title contenders for years to come.

Halladay? Many of us would love to see him in a Boston uniform, a feeling that will morph to frustration if Halladay ends up with the Yankees. Epstein knows this as well as anyone. He also knows that the Red Sox have far more to consider than just the 2009 season.

Which is why you should be shocked if he ever made this trade.

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Updated: Mar 1, 07:24 AM

About Mazz

Tony Massarotti is a Globe sportswriter and has been writing about sports in Boston for the last 19 years. A lifelong Bostonian, Massarotti graduated from Waltham High School and Tufts University. He was voted the Massachusetts Sportswriter of the Year by his peers in 2000 and 2008 and has been a finalist for the award on several other occasions. This blog won a 2008 EPpy award for "Best Sports Blog".

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