Caravan XX was built on the planning, rehearsal and execution practiced by safety, lead and wing pilots since the previous year's Caravan mission. As usual, last-minute weather, operational and composition changes tested the flexibility of our leadership and pilots and demonstrated the strength of our systems and procedures.

On Sunday, July 23, 2017, 51 Mooneys hailing from across the United States and Canada launched from Madison...destination: Oshkosh's “north” North 40. Alpha element consisted of Mooney Lead, Larry ‘Joker' Brennan and Deputy Lead, Chris ‘Toro' Shopperly. In celebration of our 20th anniversary, flying Alpha 2 was Jonathan ‘Stretch' Paul, the very first Mooney Lead for Caravan I in 1998. Revisiting Tail was Dave ‘Raptor' Piehler, who served as Tail in the original 1998 mission; along with James ‘Pepper' Oliphant, Raptor was one of two pilots flying this mission for the twentieth time.

As with last year, weather prevented practice flying in MSN and cast doubt on an on-time departure. After some coaxing from weather officer Chuck ‘Cowboy' Crinnian, the weather moved above our Go/No Go minimums at a time we also had available slots from MSN and OSH towers and MSN Approach. We launched in three-ship elements as briefed.

The flight was uneventful, with the usual occasional errant Fisk-er wanting to join up. The arrival was announced by EAA Radio and observed by the typical throng of thousands of cheering Mooniacs. OSH Tower appreciated the professionalism demonstrated by our flight, which recovered 51 aircraft and cleared the runway in under five minutes. The flight concluded with an enthusiastic debrief and appreciation for the hard work that was evidenced by each pilot's execution of the briefed plan.

Some perspective on the progress over the two decades separating the similarly-sized first and twentieth Caravans follows, as shared by the first Mooney Lead, Jonathan ‘Stretch' Paul:

“The first Caravan was nothing like the Caravan that exists today. Now there is a permanent infrastructure for formation training, management, finance, fellowship, and above all, 20 years of experience and a dedicated cadre of leaders and volunteers. For Caravan One we had little more than a simple idea promoted by e-mail. That idea was to come together at Oshkosh and to camp together. To do that we had to arrive together. Aside from that, we had nothing: no procedures, no organization, no money. We barely knew each other except through e-mail.”

“It turned out the original proposer of the idea, Akmal Khan, had never even been to Oshkosh. He had gamely suggested that we might buzz the tower on our way in. As a long-time attendee, I knew we needed a better plan and the Fisk arrival was not an option. I took it upon myself to contact Wayne Collins, the then-lead of B2OSH, the only group doing mass arrivals into AirVenture. The generosity of the Bonanza group in sharing their knowledge is a debt the Mooney, Cessna and Cherokee groups can never fully repay. Once Collins determined that we were serious, he shared his contacts within the FAA and EAA and his experience. He had two specific pieces of advice: 1) don't try to fly in formation if you are not experienced and 2) start small. (The first Bonanza group had only 9 planes).”

“With that advice, we had to invent a procedure, select a starting point, obtain the necessary FAA approval, involve the EAA, and make a whole series of local arrangements. The first piece of luck was selecting Madison as the starting point and teaming up with Wisconsin Aviation who embraced us enthusiastically (and still do today). The second amazing thing that happened was the volunteerism that sprung up spontaneously. Dave Piehler (Raptor), a Wisconsinite, handled the local hotel and FBO arrangements. James Oliphant (Pepper) went into the apparel business. Countless others pitched in to develop the procedures, organize the BBQ, set up a registration system, manage the ramp and work out the many logistical details.”

“By mid-June 1998 we had over 50 pilots signed up. The operational plan was moving into its final form. From the beginning Waldo Born, Lloyd Sterns and others lobbied for some sort of formation flight. But without training, those of us responsible for the plan viewed that as folly and dangerous. The basic plan was simple and in hindsight amateurish When the flight was released by Madison tower, individual planes would take the runway and depart at 15 second intervals (half a mile separation). The planes would fly in trail on a predefined course at 3,500 feet direct Fond du Lac airport until due south of OSH and then landing alternating on Runway 36L and 36R. The basic rule was "follow the plane ahead and maintain spacing".”

“On Caravan day we were scheduled for a 4:30 PM departure with 42 planes. At 2 PM we met for an all-hands briefing followed by the obligatory group photo. Needless to say, this first Caravan was awkward in execution. The excessive distance between planes made it difficult to keep the plane ahead in sight and impossible to judge separation. The departure and arrival rate was agonizingly slow. Enroute the planes in the rear experienced a serious whipsaw phenomenon. To make matters worse, plane number 15, piloted by "Black Cloud" Henry Hotchburg aborted with a blown jug and limped back into Madison trailing smoke. Unfortunately, with the “follow the leader” instruction, a sizable segment of the following Caravan veered off course until the situation was resolved. It is well-documented that several planes swapped positions in the procession. In any case, the remaining 41 planes landed safely to the tower's repeated "welcome to Oshkosh". Significant improvements to the "gaggle" procedures were made over the years until it was replaced by the current 3-plane element formation procedures in 2012.”

“In summary, being lead for Caravan I was probably the high point of my 50-plus year flying career and 5,000 hours. Today I marvel at the vibrant and professional organization that the Caravan has become. May it continue for a long time.”