Joined: Jan 2010
Posts: 9,797
Likes: 1,762
From: Northern California
Bikes: Cheltenham-Pedersen racer, Boulder F/S Paris-Roubaix, Varsity racer, '52 Christophe, '62 Continental, '92 Merckx, '75 Limongi, '76 Presto, '72 Gitane SC, '71 Schwinn SS, etc.
Have you oiled the headset bearings through the perimeter gap around each cup?
These headsets tend not to loosen or to get over-tightened, because of the toothed washer system of adjustment. It could have been messed with though and ended up too tight.
The bent fork is a red flag for a possibly bent steerer tube, which would induce a sensation of over-tight bearing adjustment.
If the steering pulls toward one side then the fork legs will likely need to be moved (bent, one at a time) toward the same side as it pulls toward. This symptom would be further indicated by the wheel no longer centering between the fork legs up near the crown.
But if both legs and the crown are bent to one side together, with the wheel still centering under the crown, then the fork steerer tube (inside of the head tube) could be bent by itself.