I'll have to echo what the last post says.
With respect to the original post, academic programs and "pedigree" will in general get you the upper hand with respect to academic positions and/or fellowship opportunities as often the word of mouth recommendation from known faculty or letters of recommendations will be necessary. With that said, if you're looking at private practice, then there is nothing wrong with going to a long standing community program with the caveat that you'll likely get the best offers locally where the practitioners are familiar with the quality of the program. Lastly, if you're looking at an administrative track (e.g. CMO, CFO), then of course regardless of your training program it is highly advisable that you augment your training with an MHA. MHSA, of MBA degree. Also, try and land position such as "house staff president" and administrative chief resident to show your ability to handle the non-clinical aspects of medicine.
With respect to the last two posts, I do have to disagree with the assertion that a resident from a "highly acclaimed" program might be more attractive. On the contrary, I would actually look more for a county hospital/inner city/busy community program over a traditional "blue blood" academic program as those residents often trained without fellows and had more hands on training, dealt with an equally challenging clinical volume (albeit with less zebras and more horses), and may be a little behind with respect to didactics or academic teaching, but know "survival" in the specialty at hand. With that said, there are good and bad residents, good and bad attending, good and bad bedside skills everywhere. I trained at a solid community program for residency, traditional powerhouse for fellowship, and have learned along the way to look beyond "pedigree" when hiring a partner.
Hope this helps!
I'm looking at programs as a whole also.