by Beth Bailey and Mitch Parmentier
A podcast devoted to the history of aviation, told by the aviators who were in the cockpit. Lifting the curtain on fighter pilot culture, life in the squadron, important moments in Naval history, and the legendary aviators whose stories live on long after they departed for the great O-Club in the sky.
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Publishing Since
9/29/2025
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June 16, 2026
<p>Welcome to the Fighter Pilots’ Guide to Living. Today’s guest is retired Captain Dan 'Darth' Cain. In the fifth and final episode about Darth's amazing career, we talk about his participation in Task Force 20, the initial foray into Iraq, and final thoughts on an incredible career.About Darth:Captain Dan Cain USN (Ret) was born in Lake City, FL. He served 6 years in the United States Marine Corps with a Vietnam tour in 1966-1967. He entered the Navy through the AOCS ,receiving his commission November 1974.Following his designation as a Naval Aviator, Cain reported to VS-33 in November 1975, making an extended Western Pacific/Indian Ocean deployment on the USS Kitty Hawk (CV-63). He next reported to VT-86, NAS Pensacola, Florida for Radar Intercept Officer Instructor duty. In April 1980, he traveled to "Fightertown USA", NASMiramar, California for F-14A transition training with the "Gunfighters" of VF-124.After being part of VF-211, VF-124, VF-191, VF-1, he was next assigned to Carrier Air Wing Two, as the Airwing Operations Officer from June 1988 to August 1990, and subsequently reported to the VF-21 "Freelancers" as Executive Officer, deployed aboard the USS Independence (CV-62) in the Indian Ocean for "Operation Desert Shield" and with USS Ranger (CV-61) and then back to CAG-2 for the strike planning of "Operation Desert Storm". In October 1991, he became Skipper of the "Fighting Freelancers", still assigned to the USS Independence (CV-62), permanently forward deployed to Atsugi, Japan. Cain completed his 11th cruise in fall 1992, culminating in leading the "Fighting Freelancers" over the skies of Iraq in the establishment of a "No-Fly" zone for the beginning of "Operation Southern Watch".January 1993 Cain became the staff Operations Officer for the Commander of the Pacific Fleet Fighters Squadrons, for their transition to the F-14D "Super Tomcat". Upon completion of this staff tour, he reported to the USS Constellation (CV-64) for a tour as the Air Boss accumulating two additional cruises. These sea tours added to a total of nine years at sea and to the equivalent of 14 cruises.In September 1995, Cain reported to Eglin Air Force Base, Florida for a joint service tour (J-8) as the Navy Deputy Director for the "All Service Combat Identification Evaluation Team" (ASCIET) then next as the JSOC Navy Director of a special program, “Joint Night Close Air Support Program.”Cain became the Executive Officer of Naval Aviation Schools Command, Pensacola, Florida where he was selected for Captain. He was then assigned to the staff of Commander Naval Education & Training as NROTC ProfessionalDevelopment Head.In Jan. 2003 Captain Cain was temporary reassigned overseas to Joint Special Operations Command (JSOC), Task Force-20/Special Forces in support of “Operation Iraqi Freedom”, where he was awarded the Distinguished Flying Cross and Bronze Star and numerous campaign and Joint Forces unit awards for his role in highly classified operations.Operationally, Captain Dan Cain has accumulated more than 6000 flight hours in various fighter aircraft, with over 4200 hours in Tomcats, while accumulating over 1400 carrier landings. Captain Cain has been awarded the Legion of Merit, Distinguish Flying Cross, Bronze Star, Purple Heart, Defense Meritorious Service Medal, Meritorious Service Medal with 3 Gold Stars, Air Medal with 3 Strike/Flight and V, Navy Commendation Medal with two Gold Stars, Navy Achievement Medal with Gold Star, Combat Action Ribbon with Gold Star, Presidential Unit Citations, Joint Meritorious Unit Citation, Meritorious Unit Citations, Good Conduct Medals (USMC), Expeditionary Medals, Humanitarian Service Medals, Vietnam Cross of Gallantry with Gold Star and the Vietnam Cross of Gallantry with palm and various campaign medals for military services covering the span of three wars.Captain Dan Cain has been married for 50 years to the former Kathy J. Williams of Pensacola, Florida and resides In Conroe, Texas</p>
June 9, 2026
<p>Welcome to the Fighter Pilots’ Guide to Living. Today’s guest is retired Captain Dan 'Darth' Cain. In the fourth episode about Darth's amazing career, we talk about his tour in Atsugi, Japan as Skipper of VF-21, the Fighting FreelancersAbout Darth:Captain Dan Cain USN (Ret) was born in Lake City, Florida. He served 6 years in the United States Marine Corps with a Vietnam tour in 1966-1967. He entered the Navy through the AOCS ,receiving his commission November 1974.Following his designation as a Naval Aviator, Cain reported to VS-33 in November 1975, making an extended Western Pacific/Indian Ocean deployment on the USS Kitty Hawk (CV-63). He next reported to VT-86, NAS Pensacola, Florida for Radar Intercept Officer Instructor duty. In April 1980, he traveled to "Fightertown USA", NASMiramar, California for F-14A transition training with the "Gunfighters" of VF-124.After being part of VF-211, VF-124, VF-191, VF-1, he was next assigned to Carrier Air Wing Two, as the Airwing Operations Officer from June 1988 to August 1990, and subsequently reported to the VF-21 "Freelancers" as Executive Officer, deployed aboard the USS Independence (CV-62) in the Indian Ocean for "Operation Desert Shield" and with USS Ranger (CV-61) and then back to CAG-2 for the strike planning of "Operation Desert Storm". In October 1991, he became Skipper of the "Fighting Freelancers", still assigned to the USS Independence (CV-62), permanently forward deployed to Atsugi, Japan. Cain completed his 11th cruise in fall 1992, culminating in leading the "Fighting Freelancers" over the skies of Iraq in the establishment of a "No-Fly" zone for the beginning of "Operation Southern Watch".January 1993 Cain became the staff Operations Officer for the Commander of the Pacific Fleet Fighters Squadrons, for their transition to the F-14D "Super Tomcat". Upon completion of this staff tour, he reported to the USS Constellation (CV-64) for a tour as the Air Boss accumulating two additional cruises. These sea tours added to a total of nine years at sea and to the equivalent of 14 cruises.In September 1995, Cain reported to Eglin Air Force Base, Florida for a joint service tour (J-8) as the Navy Deputy Director for the "All Service Combat Identification Evaluation Team" (ASCIET) then next as the JSOC Navy Director of a special program, “Joint Night Close Air Support Program.”Cain became the Executive Officer of Naval Aviation Schools Command, Pensacola, Florida where he was selected for Captain. He was then assigned to the staff of Commander Naval Education & Training as NROTC ProfessionalDevelopment Head.In Jan. 2003 Captain Cain was temporary reassigned overseas to Joint Special Operations Command (JSOC), Task Force-20/Special Forces in support of “Operation Iraqi Freedom”, where he was awarded the Distinguished Flying Cross and Bronze Star and numerous campaign and Joint Forces unit awards for his role in highly classified operations.Operationally, Captain Dan Cain has accumulated more than 6000 flight hours in various fighter aircraft, with over 4200 hours in Tomcats, while accumulating over 1400 carrier landings. Captain Cain has been awarded the Legion of Merit, Distinguish Flying Cross, Bronze Star, Purple Heart, Defense Meritorious Service Medal, Meritorious Service Medal with 3 GoldStars, Air Medal with 3 Strike/Flight and V, Navy Commendation Medal with two Gold Stars, Navy Achievement Medal with Gold Star, Combat Action Ribbon with Gold Star, Presidential Unit Citations, Joint Meritorious Unit Citation, Meritorious Unit Citations, Good Conduct Medals (USMC), Expeditionary Medals, Humanitarian Service Medals, Vietnam Cross ofGallantry with Gold Star and the Vietnam Cross of Gallantry with palm and various campaign medals for military services covering the span of three wars.Captain Dan Cain has been married for 50 years to the former Kathy J. Williams of Pensacola, Florida and resides In Conroe, Texas</p>
June 2, 2026
<p>Welcome to the Fighter Pilots’ Guide to Living. Today’s guest is retired Captain Dan 'Darth' Cain. In the third episode about his illustrious career, we talk about life aboard the carrier in the days when your state room could hold a water bed, a margarita machine, and chips.About Darth:Captain Dan Cain USN (Ret) was born in Lake City, Florida. He served 6 years in the United States Marine Corps with a Vietnam tour in 1966-1967. He entered the Navy through the AOCS ,receiving his commission November 1974.Following his designation as a Naval Aviator, Cain reported to VS-33 in November 1975, making an extended Western Pacific/Indian Ocean deployment on the USS Kitty Hawk (CV-63). He next reported to VT-86, NAS Pensacola, Florida for Radar Intercept Officer Instructor duty. In April 1980, he traveled to "Fightertown USA", NASMiramar, California for F-14A transition training with the "Gunfighters" of VF-124.After being part of VF-211, VF-124, VF-191, VF-1, he was next assigned to Carrier Air Wing Two, as the Airwing Operations Officer from June 1988 to August 1990, and subsequently reported to the VF-21 "Freelancers" as Executive Officer, deployed aboard the USS Independence (CV-62) in the Indian Ocean for "Operation Desert Shield" and with USS Ranger (CV-61) and then back to CAG-2 for the strike planning of "Operation Desert Storm". In October 1991, he became Skipper of the "Fighting Freelancers", still assigned to the USS Independence (CV-62), permanently forward deployed to Atsugi, Japan. Cain completed his 11th cruise in fall 1992, culminating in leading the "Fighting Freelancers" over the skies of Iraq in the establishment of a "No-Fly" zone for the beginning of "Operation Southern Watch".January 1993 Cain became the staff Operations Officer for the Commander of the Pacific Fleet Fighters Squadrons, for their transition to the F-14D "Super Tomcat". Upon completion of this staff tour, he reported to the USS Constellation (CV-64) for a tour as the Air Boss accumulating two additional cruises. These sea tours added to a total of nine years at sea and to the equivalent of 14 cruises.In September 1995, Cain reported to Eglin Air Force Base, Florida for a joint service tour (J-8) as the Navy Deputy Director for the "All Service Combat Identification Evaluation Team" (ASCIET) then next as the JSOC Navy Director of a special program, “Joint Night Close Air Support Program.”Cain became the Executive Officer of Naval Aviation Schools Command, Pensacola, Florida where he was selected for Captain. He was then assigned to the staff of Commander Naval Education & Training as NROTC ProfessionalDevelopment Head.In Jan. 2003 Captain Cain was temporary reassigned overseas to Joint Special Operations Command (JSOC), Task Force-20/Special Forces in support of “Operation Iraqi Freedom”, where he was awarded the Distinguished Flying Cross and Bronze Star and numerous campaign and Joint Forces unit awards for his role in highly classified operations.Operationally, Captain Dan Cain has accumulated more than 6000 flight hours in various fighter aircraft, with over 4200 hours in Tomcats, while accumulating over 1400 carrier landings. Captain Cain has been awarded the Legion of Merit, Distinguish Flying Cross, Bronze Star, Purple Heart, Defense Meritorious Service Medal, Meritorious Service Medal with 3 GoldStars, Air Medal with 3 Strike/Flight and V, Navy Commendation Medal with two Gold Stars, Navy Achievement Medal with Gold Star, Combat Action Ribbon with Gold Star, Presidential Unit Citations, Joint Meritorious Unit Citation, Meritorious Unit Citations, Good Conduct Medals (USMC), Expeditionary Medals, Humanitarian Service Medals, Vietnam Cross ofGallantry with Gold Star and the Vietnam Cross of Gallantry with palm and various campaign medals for military services covering the span of three wars.Captain Dan Cain has been married for 50 years to the former Kathy J. Williams of Pensacola, Florida and resides In Conroe, Texas</p>
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A podcast devoted to the history of aviation, told by the aviators who were in the cockpit.
Lifting the curtain on fighter pilot culture, life in the squadron, important moments in Naval history, and the legendary aviators whose stories live on long after they departed for the great O-Club in the sky.
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