Flying Squirrels GM Anthony Oppermann On CarMax Park, 6,040 Days & Finding an Octopus | ST E8

Anthony Oppermann is the General Manager of the Richmond Flying Squirrels and he has been part of this organization since day one off and on. He joined Jack Fitzpatrick for Episode 8 of Sidetracked near the close of the historic inaugural season at CarMax Park. Anthony was in the room for the Baseball is Back press conference on September 23, 2009. He was the GM who opened CarMax Park on April 7, 2026. That is 6,040 days from promise to reality — and he was present for both ends of it. We get into all of it — how a kid from La Grange, Texas who wanted to be a paleontologist and then a meteorologist ended up broadcasting minor league baseball for a decade, why he walked away from broadcasting, what the relationship between a minor league GM and the San Francisco Giants actually looks like, why the Flying Squirrels have never needed to lean on the Giants brand the way other teams lean on their major league affiliates, what the first season at CarMax Park has really looked like from the inside, the cat jersey story that raised awareness for the Richmond SPCA, and what happens at CarMax Park when baseball season ends. Plus The Three Questions — including a surprising answer about barrier islands, wild Spanish mustangs, and a very smart octopus. Follow the Richmond Flying Squirrels at squirrelsbaseball.com and @flyingsquirrels on social media. CarMax Park is located at 2705 North Arthur Ashe Boulevard, Richmond VA. 📻 Sidetracked airs every Friday during Fitz the Bill — 9 AM on 106.1 ESPN Richmond 🎙️ Find Sidetracked on Apple Podcasts, Spotify and wherever you listen CHAPTER MARKERS 0:00 — Welcome & The Inaugural Season at CarMax Park 2:27 — 6,040 Days From Press Conference to Opening Day 3:27 — Paleontologist, Meteorologist, Broadcaster — The Origin 5:45 — Growing Up Listening to Astros Games on the Radio 7:18 — Why He Left Broadcasting 8:25 — The Broadcaster's Perspective on Minor League Players 11:19 — What a Minor League GM Actually Does 14:30 — Minor League Baseball Road Trip & Learning From Other Teams 15:22 — The Cat Jersey Story & Partnering with the Richmond SPCA 19:04 — Waffle Jerseys & Getting Players to Play Along 20:25 — Building a Full Time Alternate vs a One Off Jersey 24:11 — Why the Giants Stay Affiliated With Richmond 28:21 — Building the Flying Squirrels Brand Independent of San Francisco 31:15 — Why Double-A is the Best Level of Minor League Baseball 33:43 — Minor League Baseball Then vs Now — What Changed 39:20 — What the First Season at CarMax Park Has Really Been Like 44:28 — What He Is Most Proud Of From Year One 48:11 — What's Coming to CarMax Park After Baseball Season 52:37 — The First Rule of Operations — Never Say It's Going Quick 54:54 — The Three Questions 55:11 — Never Say the R Word 59:52 — Favorite Richmond Experience — The Neighborhoods 1:01:54 — What Would Surprise People — Barrier Islands & The Octopus #Sidetracked #FitztheBill #FlyingSquirrels #CarMaxPark #Richmond #RVA #ESPNRichmond #MinorLeagueBall #SFGiants #RichmondBaseball #MILB #RichmondSports #804 #BaseballIsBack