Biff and his friends started building racecars with the stated goal of winning enough local races to catch the eye of NASCAR Cup Series team owners. The last of Greg Biffle's 19 Cup Series wins came at Michigan in 2013. He finished second to Tony Stewart in the 2005 Cup Series title fight and third behind Jimmie Johnson in 2008. The reality is that he probably shouldn't have ever won races at Portland. In other words, NASCAR flying is much like NASCAR racing itself.