Can "worse" sound "better" ?

Early in my pursuit of the high end, I had assembled a mixture of high end (amp) , revealing ribbon speakers, pretty good preamp and "wanna be" CD player and DAC. I decided to try some really good interconnects. Straight wire ... really expensive... like the early 80’s. I was really disappointed they were shrill and trebly sounding. I was really disappointed. I threw them in the closet. Played with copper and silver coated interconnect of much lessor value, 

Years later my system had gotten many times better. I found the interconnects. Just for fun I plugged them in. My jaw dropped they were incredibly good... transparent... incredible bass and dynamics.  Same story with a set of speaker wires. These were Transparent. Now passing all the frequency range through the wires was a good thing. 

If you have a system that has lots of high frequency hash, high frequency distortion (fatiguing sound),  with revealing speakers... then really good wires can make your system sound terrible. You want warm copper interconnects to cover up the deficiencies in your system.

Lower quality components have inexpensive power supplies and often have a lot of high frequency or noise floor you do not want to hear... so covering that up can be a good thing. This is why the Cardas strategy is to have their lowest priced interconnects and cables the warmest and least revealing and their highest end the most transparent. It is a brilliant strategy to match the cabling to the components. I used Cardas extensively early on in my pursuit of the high end. 

All, my components are top notch and natural sounding... so now I want the very best transparent wires. 

Thank you for your inputs, really appreciate different perspectives and shared experience. 

@jsalerno277

Yes, you summed it up nicely, these cables behave exactly like described between the source and my preamplifiers. (In my second system (which is no longer) I had Meridian G02 preamp  connected to Classe CA2100 power amp and all three cables exhibited the characteristics as described. 

However, now, between Krells, the Van den Hul Integration just sounds more open.with bigger soundstage and as mentioned before - with a lot more space, air and atmosphere. If I was to number my preference of cables between the pre and power it is: 1. The Integration; 2. The Orchid and 3. Frey

I am now tempted to buy another Integration just to check the sound by substituting current cable... 

@ghdprentice;  thank you, understood and agreed, went through this myself. 

@zbig06 perhaps it might be helpful to read Iconoclast Design and Technical white papers to get a basic idea of high-end audio cable are designed. It addresses LCR and dielectrics in cable design using measurements. Iconoclast was designed by a Belkin cable engineer who decided to create higher performing audiophile cables and his white papers describes the process including measurements and calculations.

Beyond basic understanding, audiophile cable companies do not reveal their secret sauce.

I think those saying synergy is the culprit here are probably right.  I also haven't had great luck with Nordost power cabling vs basic Cardas cabling.  My system is extremely revealing but I felt the Nordost made things sound more "etched" - maybe with an even more revealing system they would sound better?  But this helped me understand that synergy is way more important than price.

Also some super transparent systems can uncover flaws in mixing or recording.  I am a huge fan of Aphex Twins Selected Ambient works 85-92 but if the system is extremely revealing, the mixes sound a bit harsh and disconnected I've found.  Add a tiny bit of warmth to the system and bam it sounds way more organic.

Trust your ears.  And whenever making cabling changes I highly recommend trying at least three different cables of varying price points and construction to really determine the proper cable for YOUR system.  Best of luck OP!