Seems to be a 2 horse race imo since Dileo is in his 1st year on the job and Holmgren at least keeps the Flyers competitive every year.
Rube's smugness didn't bother me at first because he appeared to be putting together a dominant team....which he did for 1 year. But since the 2010 season ended, this team went on the decline at a fairly rapid rate and he hasn't really done anything to stop the tailspin. It seems like this team has gone full circle and we're back in 2002. They have a few decent players on the roster but they're handcuffed by some really bad contracts and are just making things worse by overpaying for players who won't make any significant impact.
Don't really need to go into details about Howie. We all know he's in over his head and is vastly unqualified for the job.
That said, I vote Rube. Howie really is the worst, but he at least has the excuse of not having any prior football experience and very little front office experience. He's simply in a position he was never qualified for in the 1st place. Rube played the game and then spent like 10 years as the asst GM under Wade and Gillick. It's pretty obvious he spent the majority of the time under Wade because this team is starting to resemble Wade's Phillies.