Compared to what?
Compared to every H-D I've ever ridden including my 2012 Street Glide and the 2014 Rushmore model I test rode
By what measure?
You'll have to be more specific. We all use different metrics when we compare products. I test rode a Chieftain and I loved it. It was smooth, had lots of torque, the fit and finish was superb, it handled very well, It was comfortable the suspension was exceptional, the sound of the engine/exhaust was nice and I could probably keep going. It reminded me a lot of a Victory I test rode a few years ago which I also really liked. I prefer the classic Indian styling over the modern styling of the Victory though and I think the cable management on the Indian gave it a nice clean look. Looks are a personal thing, so not a good measure in my opinion.
Like I said the new Indian is an awesome bike. For the type of bike it is I would buy it over another classic American model and not have any regrets.
I have only every ridden one HD, a Heritage Softail Classic, 2012 model. It was okay, but I like my Victory much better and am glad that I went with what I did.
My buddy has a Chieftain; the very first one that Chesapeake Cycle sold as a matter of fact. He absolutely loves it and I'm happy for him. I have a few miles on it and could not buy it for myself for one simple reason. It's small, compared to my bike. I'm 6'6" and can pretty much lay out on my bike and be comfortable riding for a very long distance (re: Bob's Ironbutt thread), but on that Chieftain I feel cramped. Really cramped. A lot of others have said the same...as did my buddy when he compared it to mine. He's 6'2" and claims to be comfortable on his Indian, but did say that if he were buying the bike for comfort, he would have gone with Victory. He bought the Indian for the looks (it is stunning) and because he has always wanted an Indian. I agree 100% that the fit and finish are very well done. The fly-by-wire throttle is as smooth as melted butter and the electronic windshield works very well for wind management. The stero is good, but better if you have the rear speakers that go into the saddlebag lids. Handling was good, but no better than my vic. Torque and power were underwhelming to me, but I'm making 113 HP and 115 TQ at the rear wheel (no, not stock) so it stands to reason that I was not impressed with that.
Ride what you like, be happy and make friends along the way. That's all that matters.