Pondering a pinstriped Halladay but only for a yearBy
One of the Yanks’ primary objections to any trade for Roy Halladay is the need to, in effect, pay twice to acquire the pitcher. The team will have to send some highly-touted prospects and a young Major League pitcher to the Blue Jays for the rights to Halladay, and then the Yanks would have to sign him to a long-term contract extension as the pitcher sits just one season away from a potential free agent payday.
We have, of course, been down this road before. In December 2007, the Yankees opted against acquiring Johan Santana because the team knew CC Sabathia would be available for just money after the 2008 season. This year, the team has been hesitant to leap into the Halladay fray because they know some top pitchers will hit free agency in both 2010 and 2011. Even if Doc is better and more durable than Santana, the Yankees aren’t going to change an approach that led to a World Series title.
But what if the Yankees only have to pay once for Halladay this year while gaining the opportunity to recoup some of the cost? Joel Sherman presents a one-year scenario in The Post today, and it goes a little something like this:
[O]ne faction of the Yankee front office has advocated trying to trade for Halladay, but not extend his pact. That way they would get Halladay on a very good contract for 2010 ($16 million) and then offer him arbitration after the season to secure two draft picks as a way to recoup some of the prospects given up in the trade.
According to Sherman, this idea is “not a strategy with much traction” within the Yankee Front Office, but I like the approach. It carries with it an idea that the Yankees would not have to give up as much to the Blue Jays if they aren’t requesting a negotiating window. It would simply be a player-for-prospects swap that would net the Yankees Roy Halladay’s age 33 season and the potential to pick up two first-round draft picks in the 2011 draft. With the Blue Jays are reportedly asking for a Major League-ready pitcher and an impact bat, the draft picks would definitely help offset the loss of young players.
Furthermore, Toronto could prefer this approach as well. What happens, for example, if the Blue Jays grant a team a negotiating window, but the team and Halladay can’t come to terms? Sherman, in a blog post, reported that Halladay is interested in Santana/Sabathia dollars, but Halladay will be five years older than those two were when they received their lucrative deals. It’s easy to see how a negotiating window could result in no trade.
There are, however, a few too many roadblocks for me to believe that a one-year rental would be a viable solution. First, the Blue Jays would have to feel that the Yankees’ offer remains the strongest even if other teams want the negotiating window. Perhaps, though, the other teams — assumed to be the Red Sox, Dodgers, Angels and Phillies — aren’t too keen on giving too many years and too much money for a 33-year-old pitcher. If no one wants a negotiating window, the Jays may not have that leverage. Right now, no one knows.
The other major problem is Roy Halladay’s full no-trade clause and his desire for some stability. With the no-trade clause, Halladay can veto any trade, and if a team is not willing to give him the dollars, he will simply reject the trade and file for free agency. Additionally, Halladay knows that the next deal he signs will be his last big contract, and he’ll want the stability and the guaranteed money up front. For pitchers, the end is just one arm injury away.
In the end, the idea of a one-year marriage with Roy Halladay is very appealing. It remains, however, a long-shot to come as the end to this saga. And so we wait for the Halladay sweepstakes to take shape.