Wolf is the only one that I would bench. Houston can do some damage when they are hot.
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As long as he stays healthy, I would probably start Brown almost every time out. Wood is a top 10 pitcher and a K stud, so you pretty much need to start him regardless of the matchup, except maybe at Coors. Woody Williams, when he is healthy, is almost always an excellent start. In the last three years, he has given up more than 3 earned runs only 3 times, which gives you an idea of how safe he usually is. Meche might be a bit of a shaky start, because he is pretty unproven and the White Sox offense is too good not to break out in a big day one of these days. You don't want it to happen to one of your pitchers. I would let Wolf start, since the game is in Philly, at a pitcher's park and the Astros offense tends to be far less potent away from the juice box and its tiny dimensions.
My usual thought is not to start too many SPs on the same day because the odds of all of them doing well seem long. In your case, you also have two guys going against each other. Since it appears that your league doesn't count wins or losses, this might not matter so much. Do you expect a pitchers' duel at Wrigley between Wood and Williams, or will the potent Cards' offense prevail over Kerry?
I agree with starting Brown, but according to Rototimes, he's pitching Friday against Claudio Vargas, not Saturday against Vazquez (all the more reason to start him).
Meche is going again against Colon (he won that rain-shortened duel last Sunday; will Colon balance out in his second try?) but he's been good.
The Wolf question is the toughest because Wade Miller's been less than stellar, as has the Phillies' offense.
So many questions, such tough decisions. That's why you make the big bucks as manager. I'd start everyone but Wolf and hope the wind is blowing in at Wrigley.
Big Kahuna, why would the odds of all SP's doing well on the same day be any different from the odds of all SP's doing well when the starts are spread over several days? Unless you're superstitious (a famous baseball attribute, but probably not right).
I'm no mathematician, so maybe it is just superstition, but it seems there's more disaster than success when all of your guys go at once. It's like the pick five lotto: each of your numbers has a better chance of coming in one at a time on five successive days than all five coming in on the same day. I had three guys go the other day (Millwood, Ainsworth, and Lohse): one loss, and two no-decisions. ERA around 4, WHIP around 1.6. Call me crazy, but . . . .
It's not like lotto; lotto is a game of chance, baseball is not. I'd start em' all but Wolf for the reasons previously stated. If you bench a few of them you run the risk of losing those categories b/c you'll have no more starts the rest of the week.