Bank Robber, Criminal, Pilot.
Michael Callan was Windsor’s most famous bank robber; however, his “claim to fame” was being killed in a 2013 Nashville plane crash where he was reputedly seeking out singer Taylor Swift.
Callan was born in Windsor on July 26, 1968, the fourth child in a middle-class family. After graduating from W.D. Lowe, Michael attended and graduated from the Canadian Aviation Institute in the hopes of flying for the Air Force. Unfortunately, the Air Force turned him away and that was the beginning of his fall into disrepute. Police believe he robbed his first bank in 1994, but wasn’t charged at that time. It wasn’t until he robbed 5 banks in an 11 month period during 1997 that Callan was captured, tried and convicted in late 1998; he spent 14 years behind bars, serving 100% of his sentence due to poor behaviour during his incarceration. During his incarceration, he spent time obsessing over several teenaged celebrities, including Miranda Cosgrove and Taylor Swift; upon his release, the judge put restrictions in place around contact with Cosgrove, but not Swift.
Callan landed back in jail a few months later on a couple pornography related charges. Despite so many interruptions, he managed to secure his pilot’s license and became a member in good standing of the Windsor Flying Club in 2012. On his application, he listed Taylor Swift as his emergency contact.
On October 28, 2013 Callan booked a plane and flight plan to Pelee Island for an overnight stay. The plane took off around 6pm, and he closed his flight plan (indicating arrival) two hours later. The next sighting came at around 2am on October 29th in Nashville, TN. Although never filing a flight plan, or getting clearance to fly over the border, Callan had arrived in Nashville and attempted to land his plane there without any contact with the tower. A novice pilot with training only in how to fly by sight, Callan was doomed when he hit heavy fog without the assistance of equipment or the airport and with a blood alcohol level over the legal limit. An airport worker noted the plane at 2am, but then never saw it again and assumed it had simply veered off path and moved on. It wasn’t until the morning light that the plane, charred and in pieces, was noticed off to the side of the airstrip. Fingerprints identified the only remains as being Michael Callan, who died on October 29, 2013.