Without a doubt one can build a system of highly respected components end to end, that results in poor sound. Imagine the brightest, most detailed speakers you can think of, and add an amp, preamp, DAC and cables that have similar characteristics. There might be a few people that would think this is great, but most would find it unlistenable. But the same components, sprinkled into a different system might find synergy.
I think this really gets to the heart of what makes this a hobby, or pursuit, and why it can take years to build a system. As knowledge grows and tastes changes, these systems are also replaced as we go up the chain.