Dontrelle has been on a downward spiral since his 22 win season in 2005. There have been several factors in his decline statistically. Let's look at what his chances are of making a 2009 Red Sox starting rotation and what would it take to improve.
First we need to address the current contenders for a rotation spot.
Assured a spot: Josh Beckett, Jon Lester. Daisuke Matsuzaka.
Contending: Tim Wakefield, Clay Buchholz, Justin Masterson, Michael Bowden.
This is a long shot for Dontrelle and is really asking him to be better than 15 year Red Sox veteran Wakefield and all three young guns. Masterson could return to the pen and Wakefield would also be a good long relief guy, but Willis would need to outshine them in the spring to cause that change.
Next we can look at his contract which has 22 million left over the next 2 years. The bonus over Lugo is he has options left (I think) so he could be sent down while Lujo could not. The contract is only upped by Cy Young Bonuses, which we can assume is out of the picture. As for Lujo he has 18 million left and a vesting option for 2011, but he should no longer be able to reach the PA cutoff.
So if we assume Willis comes to the Red Sox and he makes the rotation, then what does he need to do to get back to 2005 D-Train?
His K/9 has been consistent for almost every year at around 6.6, but his BB/9 have been his biggest problem. He dropped for his first three years and in 2005 got to 2.09. He then preceded to revert to higher BB/9 and has approached 4.00. This is his first need to lower the walks and keep the strikeouts over 6.5 every 9 innings. The more lefties he faces could help him though as his K/9 versus lefties has been at 9.00-11.00 since 2003 and fairly consistent.
Next is his pitches and speeds. Dontrelle has phased out his cutter since 2005 and put more emphasis on his fastball. He has also lost 2-3 mph on that fastball, but kept his change at the same speed. The loss of the cutter has really made him a three pitch pitcher and might have increased his walks as players sit on the fastball.
I suspect the Sox would try to get him to bring back his cutter or another pitch to keep the hitters guessing. If he is healthy and the Sox did trade for him I expect he would spend some time in the minors or extended spring training. With a chance to pitch more to lefties and a cutter to throw to righties he could see some success.
I would expect a 4.00 ERA in no more than 100 IP. Similar to Bartolo Colon who got 40 IP with a 3.92 ERA in 2008 with the Sox.



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