It’s not enough that you want to collect trading cards – you want to have something that has a little more than just a picture on a piece of cardboard. You have your eye on autographed hockey cards instead. Seeing a player's signature on something is a thrill, and also depending on how the card is signed, it might be worth significantly more than just an ordinary card. If the player just signs his name, that is great, but if he personalizes it – “To Michael, Best Wishes, Bobby Orr” that reduces the chances of selling the card to another collector.
The first is going to a card show – former and current players may be there signing. The vast majority of them will charge a fee, of course. With these though, it also depends on how often a person signs. If he’s known for signing a lot of things, then demand is going to be lower and the price will also be lower. If he’s not generous with his pen or he’s dead, then the value will be higher. It also depends on how good the player was – a Hall of Famer will be more valuable.
You can send them cards in the mail with a self-addressed, stamped envelope and a nice note and ask them to sign them for you. Don't be greedy and send five or six cards; just one or two and take a little time to make sure the note is short but polite and maybe a little personal for each player.
Once in a blue moon, you may get lucky and find a hockey player in attendance at a game. I had that happen once when I attended a game at Boston University and Orr was there. I got him to sign a ticket stub, but those occur very rarely and if it happens, you should consider yourself very lucky.
Buying online is considerably less personal than the other two ways, but it’s the one that requires the least amount of travel/luck. Collecting autographed hockey cards can be pretty rewarding. Anyone can buy stacks of old cards or open up boxes and saving cards is one thing but the effort to add a player's signature makes for a much more interesting experience. Collecting autographed vintage hockey card sets is the ultimate challenge but there are many who attempt it and being online is the only way to have a fighting chance to get the job done. Click here to see what's available on eBay.