I have part of my collection tied to items pertaining to the career of a guy named Josh Phelps (played with the Blue Jays, Indians, Rays, Yankees, Pirates, Cardinals and in the minors). I'll be surprised if many of you guys have any idea who he is, but back in the early 2000's, he was a rising star, even appearing on the cover of Baseball Prospectus.
Anyway, what started out as an appreciation for him for fantasy baseball purposes led to picking up one of his game used jerseys which exploded in to collecting all things related to his career. Twelve years on, I'm the proud owner of 20+ jerseys, 20+ bats, batting helmets, pictures, programs, autographs, etc.
A few years back, he was on a rehab assignment for the Giants up with the Connecticut Defenders. I jumped in the car and went up to meet him and got a couple autographs and shared a quick chat.
Later in the game, he broke his bat and came out mid-inning to give me the bat...told me to meet him after the game and he's sign it, which I did. Flash forward to the following April of 2010 and he ends up signing with the Bridgeport Bluefish. Took one of my twin daughters to the game and, despite the fact he wasn't really in the mood to sign for anyone else, get his attention and he comes over to say high and sign a couple balls for my daughter and I. Turns out a newspaper reporter took a picture of the exchange and we end up on the front page of the Connecticut Post the next day. So I have these great interactions with the guy and I send him a note to say thanks as well as a copy of the newspaper and small gift (a PSA 10 of his rookie card) for giving the broken bat to me a few months before.
Now my phone starts ringing...his wife calls, thanks me for the note and invites the family to a game. Now the kids are playing in one of the boxes at the Bluefish game, they come over to see my collection and we're having a great time hearing stories of playing for Lou Piniella, etc. For my birthday, a signed Yankee bat of his and his wife throw's in a bottle of Dreamland bbq sauce she had flown up from Birmingham, Alabama (we both love this place). Since then we've traded a few things which helped out both our collections of his stuff. You can see my Phelps collection by clicking on my signature below.
Anyway, it's not like Scott's experience, but it's been a pretty neat experience and we still keep in touch to this day...