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“Growing our family one aviator at a time” is now a reality bringing pilots from around the country to fly together, support each other, and enjoy life. 

2016 marked the group’s 7th year together. 

2017 Cherokees to OSH Core Team

Doane and Karole Bailey - 2016 Cherokee Lead

"Ferg" Ferguson - Director of Air Operations

Dwane "Ferg" Ferguson

Dwane “Ferg” Ferguson is C2O’s Director of Operations and lives in Gallatin, TN. Simply put, if it has anything to do with the flying component of this event, Ferg is in charge.  He began flying airplanes in 1968 in an Aeronca Champ while earning a degree in Mechanical Engineering.  In 1971, he joined the Air Force and began his military career flying the C-130 Hercules, including in Southeast Asia.  He finished his career after serving in Desert Storm and earned not only his Masters Degree while serving our country, but also his CFIA and A&P Certificates in his "free" time while still on active duty. During his tenure in the Air Force, he was an instructor pilot teaching formation flying in C-130's not only in VMC but on the gauges as well. Upon retirement from the Air Force in 1993, Ferg went to work for American Airlines until his retirement in 2006. Ferg currently holds a Wingman F.A.S.T. card.

American Airlines’ loss was C2O’s gain.  Ferg joined Cherokees to Oshkosh in 2010 and has been constantly refining the C2O procedures since the very beginning of the organization.  At Waupaca he’s typically in someone else’s right seat coaching them on the C2O procedures or in his Cherokee Six as “Cherokee Tail”, shepherding the group during practice flights or the actual arrival.  His teaching style is that of encouragement and praise and, as he will tell you, his whole objective with C2O is to get the whole group safely on the ground at OSH without having “traded paint”.  His balance of professionalism, humility, and personal engagement with all of the C2O participants has made each year’s event feel like a family of flyers at all skill levels who arrive at OSH safely and with a great sense of personal accomplishment. 


Chip Gentry - Director of Legal Affairs
Assistant Director of Operations

To say Chip is the Director of Legal Affairs and Assistant Director of Operations is a considerable understatement. His enthusiasm for the organization and its mission has been an inspiration and motivator for the group since the first day. And while his glass-paneled, air-conditioned Archer III is the envy of many other participants, it’s his genuine love of general aviation flying that is so palpable and engaging. Since starting flying in 2008 he has amassed over 1300 hours, his Instrument rating, and numerous endorsements. From being an Angel Flight pilot to introducing youth to the joy of general aviation through the EAA Young Eagles program to being a “carded” Formation and Safety Team (FAST) Leader, he brings a wealth of talent to C2O. And as a founding partner of Call & Gentry Law Group in Jefferson City, MO, he provides the organization with the legal talent needed to keep the organization on track as a non-profit entity.

Ferg’s right-hand man for Operations, his first focus is on making C2O a safe and fun experience for pilots of all backgrounds. While learning to fly safely as part of a large formation of aircraft flown by people one may not have met before is clearly a challenge and can be humbling, Chip’s talent, enthusiasm, and sense of humor make it easy for others to mature as Mass Arrival pilots regardless of their skill level.


Greg Hughes - Associate Director of Flight Operations - Mini-Clinics

Greg has been a private pilot since 2009 and first joined Cherokees to Oshkosh in 2013. He owns and flies a 1975 Warrior and lives in the Portland, Oregon area where he works in the cybersecurity field. He is a board member of his local EAA chapter and serves as the youth activities coordinator, managing the chapter's flight scholarships and Young Eagles program. Although the newest member to the C2O family on the leadership staff, his enthusiasm for the program is outstanding. In fact, he set up C2O’s first West Coast mini-clinic during the 2014 training season and did a superb job not only providing excellent training but also broadening the reach of C2O.

His commitment to C2O, formation flying, and organizing his mini-clinic prompted C2O leadership to ask him to take on the role of managing the coordination of the various spring mini-clinics. And although he’s currently building an RV-8, he plans to remain loyal to his Piper Cherokee roots.

Art Gentry - Webmaster

Art is C2O’s “IT guy”, however Information and Technology is just a small part of what Art contributes. While Art tends to be quiet and unassuming, he has invariably been focused on improving the C2O group’s experience as a whole. While in Waupaca for the pre-arrival training and coordination, for example, he takes the lead in staging aircraft for the taxi out for departure; no small task when one considers there are typically over 25 aircraft parked close together and in no particular arrangement.

Art lives outside of Kansas City, MO and is a member of the Masonic Lodge, which partly explains the integrity and ethics one senses while being with him – and how Chip, his son, came to have them as well.  He joined Chip the first year of C2O as his right-seater in Chip’s Archer but has been joining the group every year since then in his own Cessna 172, which, with the wings on the “wrong” side, the group fondly describes as the only fully aerobatic Cherokee of the bunch.

Doane and Karole - Director of Administration

Doane and Karole take care of C2O’s general administrative duties, including registration and sharing information via our NOTAMs.  The spark that ignited Doane's interest in aviation came from his late father, a B-24 veteran.  Although starting his flight training rather late in life, he, like Chip, can't find enough reasons to "go flying."  He and Karole proudly own and fly a beautiful Cherokee 140.  Those of you in the northwest PA area should try to attend the mini-clinic Doane sponsors each spring.

But the considerable contribution they make to C2O by handling registrations and NOTAMs is clearly overshadowed by their annual holiday gift to each year’s participants: an exceptionally well-made DVD of that year’s arrival and its planning. Each year’s DVD is clearly a work of love and of art and is filled with in-flight and on-ground videos and still pictures set to music.

Doane and Karole have been active members of the C2O family since the beginning and have been trusted to fly the “Alpha 2” position for several years. Their contributions to the program and exceptional airmanship have resulted in them being selected as “Cherokee Lead” for the 2015 arrival.


Tony and Sandra - Director of Outreach

The Union Jack on the tail Tony and Sandra’s Warrior definitely catches one’s eyes when they arrive at Waupaca from their home outside of Akron, OH and gives one a forewarning of their accent and wonderful sense of humor. As much as the US has adopted this couple from “across the pond”, they continually adopt new members to the C2O family through their good nature and friendship. Both are active pilots and essential members of the C2O leadership team: they have served as the linchpin to garnering support and sponsorship since the beginning of C2O and have been the driving force behind the annual Spot Landing Contests, where some of the many donations from various sponsors are given to winners. In fact, Tony’s prior work with Goodyear has enabled C2O to provide contest winners with new aircraft tires for the past several years.

They have also overseen the challenging task of arranging for each year’s custom shirt to be designed, ordered, and appropriately distributed to each participant. In fact, it was Sandra’s idea to have them embroidered with each pilot’s name and N number.

Ed and Dori LeBlanc - Director of Social Events

Dori and Ed have been a part of C2O with their Warrior II since the first year and live outside of Austin, TX. Ed’s 24 years in the Air Force as a Family Physician took them to a variety of places, including Germany, Norway, and half a dozen places across the US and even gained him some time in the back seat of F-16s as a Flight Surgeon. Ed has been a pilot for over 30 years, starting off by taking lessons at an Air Force Base while in medical school.

For the 2014 arrival, Dori stepped forward to arrange activities for the non-flying companions of C2O pilots by organizing a boat tour of the Chain-o’-Lakes area. They help coordinate the various non-flying activities which have become an integral part of the annual C2O experience.


Dennis and Peggy Frett - Director of Ground Transportation and Operations

Dennis coordinates the organization’s ground transportation, and aircraft parking and choreography during the pre-arrival training at Waupaca, and for social events once we arrive.  With over 2,000 flying hours since getting his license in 1995, he thoroughly enjoys the type of flying Cherokees to OSH participates in.  He has been a key member of the "family" since he joined the group in 2011 with his wife, Peggy, and their two rescued dogs, Buckwheat and Yoda.  Most of his flying time is in his 1978 Warrior II, which Peggy has soloed as well.  He retired in late 2014 from his self-owned business and is now able to work more on his own personal airfield, 1MO2, in Windsor, MO, where the two of them plan to settle down at some point.  He served on three different destroyers in the Navy as a Radarman, which explains his significant knowledge of and interest in electronics.  He enjoys volunteering at the Rockford Airfest each Spring, since it’s not terribly far from his current home in Hampshire, IL.



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