During the 2007-2008 offseason I kept reiterating that Bill Smith made the mistake with Johan Santana by never focusing on the one player he wanted. Instead of making Phil Hughes a priority and being flexible with the surrounding package, he got greedy and asked for Wang, Cabrera, and a prospect. This strategy turned the Yankees off and landed Johan Santana right in Omar Minaya’s lap.

Frank Piliere is a former scout for the Texas Rangers and national baseball analyst with Fanhouse. Yesterday he wrote that if the Jays and Yankees decide to work on a deal for Roy Halladay, Toronto GM Alex Anthopoulos should make Phil Hughes the priority while the Yankees should push for Joba Chamberlain. Take this very telling quote by Piliere:

There’s a good reason that Chamberlain shows flashes of brilliance but rarely maintains it for long stretches. When he has his good stuff, especially out of the bullpen, he has two above-average pitches, including a 7 slider on the 2-8 scouting scale. The problem is when things aren’t going his way and his high-effort delivery gets out of sync. Therein lies the difference between him and Hughes. Hughes has shown the ability to change his strategy, make adjustments and rely purely on command at times.

Here is the key point about why I wouldn’t pass up Halladay, especially for Chamberlain, in any deal:

You can say what you want about the Chamberlain starter-vs.-reliever debate, but given his skill-set this isn’t a pitcher who figures to improve on what he currently is as the years go by. Some pitchers rely on stuff, others on pitching aptitude and command, while a select few are the total package.

I never have questioned Chamberlain’s ability to throw hard. As Howard Megdal pointed out on last night’s show this very raw pitcher has a career 4.18 as a starter in the American League. My issues are with his mental makeup, weight, mechanics, and baseball intellect. I also worry, as evidence by his arrest last winter, that this is a guy more concerned about playing the part of a big leaguer than actually working hard to be a big leaguer. The most damning part of Piliere’s analysis is he thinks Chamberlain won’t get better as he ages. That’s scary! All this is speculation, but Piliere joins a long list of scouts that continue to have their doubts about Chamberlain. I always seem to think where there is smoke there is fire.

If Anthopoulos wants to learn from history (didn’t I say you can learn more from history than numbers yesterday?) he should do the opposite of Bill Smith. Focus on one player, in the case of the Yankees it should be Phil Hughes, and be open to negotiating the rest of the package. The Yankees have every right to balk at giving up a Montero or Austin Jackson along with Hughes. In the end Phil Hughes for Roy Halladay is a great deal for Toronto – better than draft picks in my opinion. However, if I am the Yankees, Chamberlain would be the stock that I send packing before the bubble bursts.

Tags: Alex Anthopoulos, Frank Piliere, Joba Chamberlain, New York Yankees, Phil Hughes, Roy Halladay, Toronto Blue Jays