Well, the problems start to arise when two parties start vying for Pegula's ear. This probably won't happen in the early honeymoon phase, but with careers on the line and type-A personalities, it's safe to say it will at some point (you want to succeed or fail on your own terms - not someone else's mistake). Also -- and this may sound like school playground politics -- if one party is perceived as "schmoozing the boss," it gives the impression of a power grab and could foster resentment between the two.
That was my take on it too Dibs, until I read the above quote. Maybe Whaley just doesn't understand everyone's exact roles? Why would he think it would ever go to Russ??
Most teams outline a specific hierarchy such as Owner -> GM -> Coach to define a clear chain of command. I don't think our triumvirate will work for the reasons I mentioned above. Then again, if we go 12-4. none of this will matter. However if we slip back to 6-10, it's a recipe for a front office meltdown.