Ron Darling

I met him at the visiting team's hotel in 2015, when the New York Mets, whom he was there as SNY's play-by-play announcer, came to play the Tampa Bay Rays.

Ron signed a 1991 Leaf card #378.

http://www.baseball-reference.com/players/d/darliro01.shtml

Reggie Jefferson

I met him at the Tampa Bay Rays Fan Fest at Tropicana Field in St. Petersburg, Florida on February 22, 2014.

Reggie signed a 1991 Leaf card #514.

http://www.baseball-reference.com/players/j/jeffere01.shtml

Mike Kingery

I met him at Jack Russell Memorial Stadium in Clearwater, Florida in 1996, when the Pittsburgh Pirates came to play the Philadelphia Phillies in a spring training game.

Mike signed a 1991 Leaf card #224.

http://www.baseball-reference.com/players/k/kingemi01.shtml

Mike Huff

I met him at a celebrity golf tournament at Lansbrook Golf Course in Palm Harbor, Florida in 1996.

Mike signed a 1991 Leaf card #BC22.

http://www.baseball-reference.com/players/h/huffmi01.shtml

Leo Gomez

I met him at Jack Russell Memorial Stadium in Clearwater, Florida in 1995, when the Baltimore Orioles came to play the Philadelphia Phillies in a spring training game.

Leo signed a 1991 Leaf card #35.

http://www.baseball-reference.com/players/g/gomezle02.shtml

Daryl Boston

I met him at Dunedin Stadium at Grant Field in Dunedin, Florida in 1994, when the New York Yankees came to play the Toronto Blue Jays in a spring training game.

Daryl signed a 1991 Leaf card #202.

http://www.baseball-reference.com/players/b/bostoda01.shtml

Jose Mesa

I met him at Jack Russell Memorial Stadium in Clearwater, Florida in 1992, when the Baltimore Orioles came to play the Philadelphia Phillies in a spring training game.

Jose signed a 1991 Leaf card #166.

http://www.baseball-reference.com/players/m/mesajo01.shtml

Gregg Olson

I met him at Al Lang Stadium in St. Petersburg, Florida. It was the first spring training game I had attended in March 1992. He had the day off and was seated a few rows behind me at a Baltimore Orioles vs. St. Louis Cardinals spring training game.

Gregg signed a 1991 Leaf card #519.

http://www.baseball-reference.com/players/o/olsongr01.shtml

Joe Carter

I met him at Englebert Complex, the Toronto Blue Jays spring training facility in Dunedin, Florida in 1992.

Joe signed a 1991 Leaf card #353. Two Springs later I attempted to get the March and August 1993 Beckett Baseball Card Monthly issues signed. The March issue was easy to get, he even took the time to personalize it for me, which I love. The August issue was a little tougher for me. Roberto Alomar and John Olerud were fairly easy to get since they were very willing signers for anyone who asked. For weeks Joe's autograph was missing from this cover. I'd bring it with me to each Blue Jays spring training game, hoping to finally have all 3 signatures.
One day, my brother, Brian was asked to be a bat boy for the game. Before the game had started, I handed my bother the magazine hoping he could get it signed. A few minutes later he comes out and hands me back the freshly signed issue. Mission accomplished.

http://www.baseball-reference.com/players/c/cartejo01.shtml

Turner Ward

I met him at a celebrity golf tournament at Lansbrook Golf Course in Palm Harbor, Florida.

Turner signed a 1991 Leaf card #449.

http://www.baseball-reference.com/players/w/wardtu01.shtml

Mike Timlin

I met him at Lansbrook Golf Course in Palm Harbor, Florida. He was another guy that I used to bump into a lot. One of my favorite memories was seeing him in a Target store a week after the 1992 World Series had ended. I told him his toss to first was the best I had ever seen. He got a laugh out of that.

Mike signed a 1991 Leaf card #525. A year or so later he signed an 8x10 glossy for me.

http://www.baseball-reference.com/players/t/timlimi01.shtml

David Wells

Now we’ve reached 1991 and the first autograph that officially began my hobby.

My friends and I would always putt on the practice putting green at Lansbrook Golf Course in Palm Harbor, Florida. One day an employee approached me and asked if I had heard of David Wells. Being a huge baseball fan, of course, I told him yes. That’s when he told me that he was currently playing the course. I rushed home and grabbed what I felt was my nicest-looking Wells card and a black Sharpie. I’ve always kept my cards in alphabetical order, so finding cards has always been an easy task. The employee also told me about several other baseball players that were regulars. It became almost a daily thing where I would go to the course to see what players were playing that day.
The practice putting green is directly across from the 9th hole and the clubhouse is right there between them. Usually, the golfers will finish the 9th and then grab something to eat or drink before continuing. I was told that Wells had not yet gotten to the 9th, so I sat at an outside table, studying the card, hoping that he would be easily recognizable to me. When he approached, I nervously asked him for an autograph. He was extremely nice and took the time to sign the card. I later discovered that he lived nearby. Since this first encounter, I have bumped into him numerous times. 20+ years later and I still see him around.
I hate being greedy when it comes to collecting autographs. I’m happy with just getting one and never asking again. Early on, sometimes I’d get a card signed and then later discover that player graced a magazine cover or had a glossy 8x10 made of him. When it comes to large photos, I always ask to have them personalized. I like when they take the time to learn my name but it also shows them that I am not looking to profit off of their signature.

David signed a 1991 Leaf card #140. A few years later, after his season with the Detroit Tigers, I asked him to sign an 8x10 glossy.

http://www.baseball-reference.com/players/w/wellsda01.shtml