My 5 Questions for Dan Winslow

(There are at least 5 questions to ask both Gomez and Sullivan, but let’s start here, with Winslow. – promoted by Paul R. Ferro)

Yesterday, BNCordeiro shared a very legitimate concern he has about Dan Winslow’s candidacy in the special election, how Winslow appears to be presumptively dismissing certain constituencies that are fundamental to Republicans and to the conservative movement.  Admittedly, I’m leaning strongly toward preferring that Mike Sullivan win the Republican nomination for US Senate in the special election Republican primary.  Still, if Dan Winslow were to adequately answer these questions, it might help me warm up to him.  For the sake of discussion, these are the questions I would ask Dan Winslow if I could.

1. Why did you, Dan Winslow, give $500 to Martha Coakley, and do you regret it?

2. The Attleboro Sun Chronicle reported that you, Dan Winslow, are “willing to consider President Barack Obama’s call for closing tax loopholes to raise revenue.”  Is this accurate?  Since “closing tax loopholes” is just a euphemism for raising taxes (heck, we all remember Mitt Romney’s “fees,” right?), and Republicans in Washington have already given Obama tons of new taxes in their latest tax negotiation surrender, why would you raise even more revenue through more taxes?

3. I was impressed that Mike Sullivan was able to get enough signatures to get on the ballot using just supporters and volunteers.  That’s a ground game!  And it reminded me of Jim McKenna’s valiant effort.  Why should I have faith, Dan Winslow, that you will have a strong enough field operation to compete with the Beacon Hill Democrat Union machine when you had to give your own campaign $100,000 (That’s almost your entire 2004 salary! See below.) to pay for signatures to get on the ballot?  Mike Sullivan got it done, so why couldn’t you?

4. Lefties like Blue Mass Group and Rachel Maddow made fun of you for pandering to us after you said that you didn’t like being in yacht clubs, even though you were a board member of a yacht club.  (We don’t need more lefty media distractions like Scott Brown’s secret meetings with kings and queens.)  Also, the Boston Herald informed us that your income went from $120,000 in 2004 to over half-a-million bucks in 2010.  When my guy Howie Carr talks about the Beautiful People, well, you get the picture.  Why, Dan Winslow, are you trying to act like you are a middle-class regular Joe when you aren’t?

5. Call me crazy, but I want Republicans to support other Republicans.  Why would you, Dan Winslow, work in 2012 for an unproductive effort like Americans Elect that would only serve to weaken the Republican nominee’s chances against the incumbent Democrat President Obama?  (Heck, the only thing Americans Elect accomplished was spending $1 million in support of a US Senator, Angus King of Maine, who is caucusing with the Democrat party!  You worked for that!)

I think these 5 questions for Dan Winslow are tough questions.  They are supposed to be tough questions.  If Dan Winslow could answer all 5 of the questions, I could consider him against Mike Sullivan, maybe, but, for what it’s worth, these are some of the big sticking points.  Admittedly, I do think that Dan Winslow will have a lot of difficulty answering these.  (There is a reason Mike Sullivan can call himself “tested and trusted.”)

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