I used to do this, also, as a kid. Back then, I would send a card to the player/manager in care of the team. I began sending a SASE with my request after receiving my signed Bill Virdon (Astros manager) back with a kind, short note from him with the tip that I would have better luck by sending a SASE With future requests. Prior to that, I received Don Money, Mike Schmidt, Bill Virdon, Dave Winfield, Dave Chalk, Johnny Bench, etc. all without sending SASEs. Often times, I would also receive a team-issued card or postcard signed as well, or in the case of Bench, a Reds logo decal.
I still send a few (2-3) a year; most recently Jim Sundberg (to his address in Arlington) and an old (pre-1976) NL Spalding ball to Randy Jones through his BBQ website contact information. He was kind enough to reply and follow-up via email.
I recommend the website Star Tiger to obtain addresses and see the validity of addresses posted. The fee to join is nominal.
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