Or maybe the reason Habs GM’s can’t fill the holes is because the highly skilled free agents just don’t want to sign and play in this city
I think there is no doubt whatsoever that this is a problem for Bergevin and whomever else might be GM. It's mostly the high taxes, and as GM you have to tell ownership that they simply have to pay guys more to equalize things but under the salary cap it's hard to do. Salary caps do not adjust based on taxes the athlete has to pay.
A few years ago I had a conversation with Darian Durant, who was then the starting QB of the Montreal Alouettes. I had no idea who he was but he came into Deville Dinerbar, alone, and sat a few stools down from me at the bar. Eventually I struck up a conversation with him which started when he told the waiter he did not know what to order and I gave him some suggestions. We then started talking and I learned he was QB for Montreal Alouettes and he told me he had played elsewhere in the CFL, and Montreal had signed him. I asked him how he liked Montreal and he said he loved the city but hated the taxes and the weather. He was paying over half his salary in taxes and that's a lot of money and more than what he had paid in his other CFL stops. He was from South Carolina I think, and had starred for the U of North Carolina in college. He was I think kind of homesick at that point. Since he was alone I had the impression he had family and girlfriend back in the USA. But with him mainly the taxes were a big shock. The conversation opened up my eyes to the fact that these athletes do not necessarily see Montreal as a great landing spot. In the case of Durant, he was at the end of a long and good career as a CFL QB and it was a final paycheck. I did not ask him, but he probably did not have many other offers as he was around 35 at that time. Montreal at the time needed a QB and he did start but only 1 year and then I think he retired. At the time I talked to him he knew he was at the end of the line. Was an interesting guy to talk to.