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RIP, Little Jimmy

Longtime SSS writer and reader James Osborn passed away late last month

It was gibby32 who delivered the news to us this morning, just a comment on a thread, that James “Lil Jimmy” Osborn had passed away on October 22.

Osborn was a longtime member of South Side Sox, joining a little more than nine years ago and posting 38 stories and 14,338 comments in his time here. He was a valued SSS prospects writer during both the Jim Margalus years, as well as with me, in 2019. And in addition to his numerous stories (usually focusing on local Illinois-Indiana draft prospects), Lil Jimmy posted countless comments on upcoming/developing drafts, and told terrific anecdotes about his days opening up the Stadium Club at new Comiskey.

Via his Meet the Players, Osborn revealed his all-time favorite White Sox player as Hoyt Wilhelm. He also told an amazing story about his favorite baseball movie, Field of Dreams:

I was so choked up after the movie, I couldn’t speak. My girlfriend and I walked out to see my old pal Ben Hollis (from Wild Chicago). I had to introduce them, and could not remember my girlfriend’s name. She was so pissed at me, I asked her to marry me to get off the hook, and 29 years later ... turns out ... good idea.

Osborn wasn’t name-dropping that introduction between future wife Linda and Ben Hollis; Lil Jimmy was an actor of some renown, with gigs at Second City and at the Steppenwolf and Goodman. Among many roles was at least one tailor made for him, sportswriter Oscar Madison in “The Odd Couple.”

I’d met Lil Jimmy only briefly, but was thrilled to have him join us on the South Side Sox masthead. His takes on prospects were a little spicy, but usually spot-on.

Although Osborn’s activity here waxed and waned, I believe I did see comments from him last month. He was tweeting @JamesOs30988211 as recently as October 18, with a very interesting name for the next White Sox manager.

Please, feel free to drop in any memories of him in the comments. Lil Jimmy was an absolute stalwart here at South Side Sox, and he will be missed.