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Like Willravel said, how is your boss likely to take it? Has your boss been managing (and managing successfully) for a long time? Or, have his actions been costing your company in both tangible and intangible ways? And more importantly, does your manager realize this is the case with any other projects?
I've been in management for over ten years and I've learned that listening to who you are managing and gaining their trust is essential. Management is about building relationships. Both ways. Up and down the chain.
That said, do you feel you have a trusting and open enough report with your boss to tell him the straight truth?
Has he consistently and openly asked for feedback and reacted well when the feedback was given, even if it wasn't always pleasant or ego-stroking to him personally?
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