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I have several signed baseballs from players I met to gain their autograph, including Kirby Puckett. Before his death his autograph was like $60 for a baseball and it's now $180 (or more, I haven't checked since November).
Not to be morbid, but I would think it's better to wait until they pass on. (too morbid even for me, but Kirby was still relatively young when he died, meaning that if he was a prolific signer, the next 40 years (when he could have been 80) will be a test of how many of his signatures survive.
Ripken sounds like a prolific signer (after all he signed 2632 balls in one go) and he's also a good guy, but that hurts the value of the autograph. Kirby and Cal were probably worth the same amount of money (baseball) but Cal was more in demand. Now that Kirby has passed on, his autographs are worht more than Cal's. Someone like Ken Griffey Jr or even Mark McGwire, who probably don't like signing will be worth more than Cal because they are quite famous players and are harder to obtain.
Better to wait until they pass on to sell the autographs. You should do some more research on how much Ripken signs autographs. I had a book from 5-6 years ago of addresses of movie stars, players, and such. They also put a note after their name to show how easy or how hard it was to get certain autographs. Of the people whose signatures I've seen (I don't necessarily own all of them):
Queen Elizabeth II: I am still amazed to see her autograph, even in museums. Really the only time you can obtain her autograph is recieve a royal honour (Two members of our family, one on my side and one on my fiancé's, recieved their OBE's from her), a christmas card (WHO would get them? Only close friends and staff of the Queen), a 60th anniversary card (if you and your spouse, living in England or any other Commonwealth realms, have been married this long, it's a LONG time and the Queen sends a card to congratulate you on being married THIS long!)
I'd say with that on my mind, she's the hardest to get. Difficulty rating 10/10
George Harrison: He was quite a prolific signer when he was with the Beatles in their heyday. When Beatlemania hit, he became much more reluctant to sign. After he was nearly stabbed to death, he REFUSED to sign autographs. My friend got a Christmas card from him, signed "Jorge Arias" not "George Harrison". He knew the value of his autograph and even if it was his friend, he didn't want the signature to be sold.
I'd say, he was a quite prolific signer but once Beatlemania hit, he became more difficult to obtain. Difficulty rating 8/10.
Kirby Puckett: I'd say the same about him in regards to George. Prolific signer then until he was hit in the eye with a baseball he retired and did a few charity events. Then a woman accused him of sexual harassment he became harder to obtain. Then he died at a young age as well. Difficulty rating 6/10.
Bob Hope: Very very easy to obtain. He was a wonderful guy and didn't mind signing autographs. As he has passed on as well the difficulty of obtaining his signature becomes harder each year, 4/10.
I would say that as Cal is still alive and is a good guy (relatively easy to obtain an autograph from), he'd be a 2 or 3 out of 10 in trying to obtain his autograph. A good benchmark for you to look at is Mickey Mantle. He lived a long time, but was quite happy to sign autographs. His autographs are still in demand and they go up in value each year. I remember when Mantle was still active and writing books, his autograph was like a modest $80, now it's hundreds and hundreds of dollars.
It's more about how often Ripken signs than not. The most I've seen on Ebay for Ripken is a signed baseball card fo $125.95.
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