With less than three weeks until the July 31st MLB trade deadline, baseball executives and fans alike are beginning to get antsy over the prospect of a marquee deal that could shake up the balance of power as the playoff push begins. This time last year, CC Sabathia had already been dealt to the Milwaukee Brewers, catapulting them to their first playoff appearance since 1982. Other big names dealt before the deadline included Mark Teixeira, and of course Manny Ramirez and Jason Bay. Each player was an integral part of their new club’s success and eventual October run.
This time around, the biggest name being bandied about is Toronto Blue Jays ace Roy Halladay. With a year and a half left on the hurler’s current contract, Jays GM J.P. Ricciardi hopes to capitalize on Halladay’s strong start to 2009 and restock his farm system with young major league-ready prospects. With the paucity of quality starting pitching in baseball, there is obviously a huge market for Halladay, especially among contenders.
Somewhat surprisingly, the Red Sox are among the teams being linked to Halladay, despite the fanfare about how much depth the Sox have at starting pitcher. As is the case with every negotiation for a star, the Jays are looking for a lot in return for Halladay’s services, and the Red Sox fit the mold of the team that has what Toronto wants. The Red Sox currently boast the 7th best farm system in baseball according to ESPN’s Keith Law, with three of their top four prospects being pitchers with major league experience. Other teams in the Halladay sweepstakes include the Philadelphia Phillies, St. Louis Cardinals, New York Mets, Texas Rangers, and the — wait for it — New York Yankees.
There hasn’t been as much trumpeting of the Sox starting rotation depth lately — due in large part to the disappearance of Daisuke Matsuzaka, and the streaky performance of John Smoltz. While Jon Lester and Josh Beckett have been solid lately, the search for the essential third guy in the Sox rotation doesn’t inspire much confidence.
Tim Wakefield is having a great year, and his first All Star nod is proof of that. “Great” would not be a word to describe his career playoff stats, however. Brad Penny has also served his purpose for the Red Sox well, with 9 quality starts. Despite pitching well, he hasn’t won since June 23rd, and hasn’t pitched into the 7th inning since May. Penny is also a historically poor 2nd half pitcher, which is worrisome.
The Red Sox seem unwilling to hand the keys to the 5th starter spot to either Clay Buchholz or Michael Bowden. Their one opportunity to do so came in April during Daisuke Matsuzaka’s first DL stint. Instead of opting for one of their young Pawtucket arms, the Sox turned to Justin Masterson to come out of the pen to start in Daisuke’s place. With that hesitance, the Sox are even more unlikely to trust a young arm as the third starter in October unless they are absolutely forced to.
Speaking of those young arms, a deal for Roy Halladay would undoubtedly include at least Buchholz, Bowden and more. Ricciardi has said that he is looking for five top prospects in order to get a deal done. While high demands are common in the beginning of a negotiation, he isn’t far off in judging Halladay’s value. Of all of the teams previously listed as in the running for Halladay, only the Mets and Yankees have farm systems ranked lower than the Sox according to Baseball America. Don’t shed a tear for the two New York clubs, though, they can remain in the running for Halladay if they take on the large contract of Jays OF Vernon Wells.
Ricciardi’s demands will undoubtedly come down as time passes without there being serious suitors. And with each passing day, time is coming off of Halladay’s contract, pushing him closer to outright free agency. For now, however, five top prospects for a guy a lot of teams covet isn’t that outrageous.
If the Sox were to deal for Roy Halladay, they would negate their own starting pitching depth, or at least cancel it out. Instead of having strength in numbers, the Sox would have a front-loaded rotation of Lester, Beckett, and Halladay. While that could be a dominant rotation for any playoff series, quantity may be a better option than quality when factoring in injuries. If one or more of that proposed threesome were to go down with an injury, the Sox rotation could be vulnerable as a unit.
On top of that, dealing Buchholz and Bowden for Halladay would obviously make it impossible to use the valuable chips in another trade to fill a more glaring hole in the Sox lineup. David Ortiz’s early 2009 scare and Mike Lowell’s uncertain injury situation necessitates the Sox at least sniffing around for a bat. Finding a full-time shortstop and the catcher of the future are also pressing concerns for the Sox. Roy Halladay is a bona fide ace, and may be the best pitcher of this generation. Unfortunately for the Sox, he is apparently becoming available at a time when the Sox aren’t in dire need of him. Even still, the Sox are not turning up their noses at an opportunity to acquire him.
Any deal for Halladay would require the team getting the ace to extend him beyond 2010. Unless Halladay isn’t dealt until next July, teams will not mortgage their entire farm system for an 18-month rental. By next year’s trading deadline, Halladay would be more rental-friendly from a financial standpoint, with a more affordable pricetag in terms of prospects required for him.
The possibility of extending Halladay, or trading him at all, rests ultimately with Halladay. While he has expressed an urge to leave Toronto, he retains a full no-trade clause, and can choose his destination. Unfortunately for Ricciardi, if no serious offers are presented for him, or if Halladay is picky about his new team, the Worcester native might not be a Blue Jays employee in 2010.
Luckily for Sox fans, and potentially for Ricciardi, Halladay has said before that he enjoys Boston and wouldn’t mind playing here.
Even still, factoring in Halladay’s no-trade clause, and the current hefty asking price, the most likely destination for Halladay in 2009 would be staying in Toronto. As Halladay’s contact begins to expire, his asking price will inevitably go down. Teams looking to make a run in 2010 may be more willing to make the one-time rental for a shot to win it all.
That type of mentality may actually increase the market for Halladay beyond the obvious contenders and major market clubs. The Milwaukee Brewers traded four prospects for CC Sabathia in 2008 in order to take a one-time shot to win it all, without a plan to extend his contract.
It is impossible to predict where teams will be this time next year, and how desperate they will be for a front of the rotation starter. For now, however, the Sox don’t have a dire need for Halladay. Then again, a chance to land the best starting pitcher in the game doesn’t come around often.
Much in the same way that Halladay will most likely remain in Toronto, the Red Sox are unlikely to make a big splash this July. The Sox didn’t make any major moves during the offseason, yet they find themselves with the best record in the AL at the All Star Break, without any immediate glaring holes. The old adage is that if it isn’t broken, don’t fix it. The Sox will likely emulate that adage and make only a minor move for depth in the infield, pending Mike Lowell’s availability for the second half.
It’s not as if reality will stop fans from coveting Roy Halladay. And until the Sox are no longer linked to him in trade rumors, the droolfest will continue.
