The Misery Machine8 Dec 2025

The Case of Dereck Cummings II aka Antwan Miles

In the nightlife pulse of Orlando, Florida, 29-year-old Dereck Cummings II, better known as Antwan Miles in his community, was building a name for himself. An aspiring rapper, a rising club promoter, and a father of four with another baby on the way, Dereck spent the night of January 29th, 2023 doing what he loved: bringing people together. His final event at Labelle Caribbean Restaurant was supposed to be another step toward the future he was striving to build.
But just after the music faded and the crowd dispersed, tragedy struck. Dereck was ambushed and gunned down in cold blood in a parking lot; an attack investigators say was carried out by 21-year-old Daquan Woods and 28-year-old Bobby Houston Bridges III of Apopka. What began as a night of celebration ended in gunfire, chaos, and the heartbreaking loss of a young father whose dreams were on the verge of becoming reality.
This week, we’re walking through the final hours of Dereck Cummings’ life, the events that led to the deadly confrontation, and the investigation that quickly zeroed in on the men accused of taking his life. This is a story of ambition, betrayal, and a community left grieving a man who never got the chance to see his children grow up. This is the case of Antwan Miles aka Dereck Cummings II.

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#themiserymachine #podcast #truecrime

Source Materials:

https://www.zandersfuneralhome.com/obituaries/Dereck-Cummings-Ii/#!/Obituary

https://www.wftv.com/news/local/family-man-community-holds-vigil-local-rapper-killed-casselberry-shooting/L6IRPGMTDNFPJIIUND5TPIUFFI/

https://www.youtube.com/@AntwaunMiles/videos

https://www.facebook.com/groups/imissmys/permalink/1563836420928959/?rdid=EhiqHCJru1fTMzzT#

https://www.villageofloveinc.org/

https://www.youtube.com/watch?v=1AglwWbuRx8

https://www.youtube.com/watch?v=38boxmXMWZE

https://www.facebook.com/marlin.drock

https://www.facebook.com/profile.php?id=100010416240112

https://www.facebook.com/tuwananleatrice

https://x.com/StephBuffamonte/status/1619844993790922760?ref_src=twsrc%5Etfw%7Ctwcamp%5Etweetembed%7Ctwterm%5E1619844993790922760%7Ctwgr%5E2deec2b21c2328963e52303389dcd57a6bdf8bdc%7Ctwcon%5Es1_c10&ref_url=https%3A%2F%2Fwww.fox35orlando.com%2Fnews%2Fvictim-in-deadly-casselberry-shooting-on-caper-lane-identified

https://www.fox35orlando.com/news/victim-in-deadly-casselberry-shooting-on-caper-lane-identified

https://www.clickorlando.com/news/local/2023/03/31/casselberry-police-chief-to-provide-update-on-deadly-shooting/

https://www.wftv.com/news/local/man-arrested-deadly-shooting-casselberry-father-entertainment-promoter/UMABEEX2WNFRPJDJRQB3XCFDEY/

https://www.wftv.com/news/local/second-man-arrested-after-deadly-shooting-casselberry-father-entertainment-promoter/FZ63RD6XGFCYBEONHZSM3PZJVE/

https://www.clickorlando.com/news/local/2023/04/03/man-arrested-months-after-fatal-shooting-near-casselberry-condo-complex-police-say/

https://www.seminolesheriff.org/webbond/

https://www.wesh.com/article/casselberry-shooting-arrest/43489296

https://www.courtlistener.com/docket/64899036/united-states-v-bridges/

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