This Gimmick Bombed

I'm not making this cover letter up, folks.  Here's the bodacious lead-in:

•  “I sincerely hope I am not too late with this letter.  My very well-connected CEO friend and colleague (who always seems to find out about these things before anyone else) told me of your very sensitive CFO search and suggested I contact you immediately.”

Next Blunder:  

“I'm no silver spoon preppie.  I paid for the majority of college through work, scholarships and loans.”

An attempt at impressing insults, instead.  Now he uses a derogatory term (silver spoon preppie) which was sure to insult the preppies who read his letter, and make the others wonder about his discretion.

And here he goes again:

 
This guy had an MBA from a Top Five business school.  That alone should have gotten him attention and interviews.  It arrived in the 2002/2003 recession, and I think he had been out of work for almost a year, so he must have been desperate and feeling that he had to really do something eye-popping to separate himself from the pile.  His employment record wasn’t pockmarked and full of job hopping, and a straightforward approach, which highlighted achievements and skills, would have been far more effective for him.