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Playing The Oregon Trail with UVa Coaches

Let's imagine the University of Virginia athletic department decided to send an expedition across the country in 1848. Let's also imagine they chose a group of five modern coaches to form this gang of explorers. Solid premise, right? Join me on the adventure:

Our first major decision: Be a banker from Boston, carpenter from Ohio, or farmer from Illinois? Well only one of those is ACC country and I assume the VAF support resembles that of a 19th century banker, so we're going with that.

Who's going to lead this group of coaches? Clearly we could go with National Champion Brian O'Connor, but my trust lies in Tony Bennett.