Quite frankly, their biggest problems have been
1. Lack of innovation. They have been relying on the same models of the same guns to carry them through forever. The model 70 bolt action is a fine hunting rifle, but it competes with the Remington 700 and the much cheaper versions produced by Savage, as well as Weatherby, etc. There's nothing to give one a competitive edge over another, and Winchester is the only one of the group that wasnt manufacturing any rifles overseas. (By the way, the USRA holding company is in Europe, but all Winchesters were manufactured in CT). The model 94 lever action is (as noted) a fine mid-range deer rifle and has seen some resurgence with the popularity of CAS (cowboy action shooting), but it is not as popular as other brands and other models that are either manufactured overseas or have more variants to draw more interest. The model 1300 shotgun suffers from the same problem. Its too damn expensive when compared to its competitors, and not nearly enough options.
2. Labor. Most of Winchester's employees in the CT factory have 30 years+ of time in with the company. Many of them are 2nd or even 3rd generation Winchester employees. While the union employees did take some cuts a few years ago in an agreement to try to keep the factory open and running, the costs associated with paying 30 year veterans at even the cut union scale wages was too much. Its not like a percentage of their workforce could be retired early. No matter what choice they made, their options were severly limited from a financial standpoint, considering the amount made per year on Winchester products.
3. Shrinking market share. Relates to #1. With no new products to expand their lineup and attract new customers, and a fairly reliable product that doesnt need replacement often, and higher prices than their competitors on the products they DO offer, Winchester saw their share of the market grow smaller and smaller every year. Meanwhile, Italian and Chinese companys have licensed the right to manufacture copies of classic Winchester models to market to CAS shooters and collectors, and are selling them in large numbers. The quality is not as good, but they are available and affordable.
4. Lack of intelligent management. I really think there's still room for them, if they could get a management team that understands the American gun market and can change their lineup to match consumer demand. People will pay more for a REAL Winchester, if you market things right. Especially if you keep quality high. There's always a market for quality. USRA has no stake in making sure Winchester succeeds. It was just a way for them to make money. I also dont think its entirely a union problem. Ruger is an all American company, paying union scale wages to its workers, and its doing quite well. Winchester could too. We have Brownings made in Japan, S&W made with parts from China, Remingtons made with Chinese and Russian parts ............ To me, buying foriegn made Winchesters (except for the odd collector pieces) would be like buying a Japanese made '57 Chevy.