Kammala jumla mai zuwa: Dale Earnhardt ya hayar da Waltrip don ya tuka sabuwar motar Chevrolet Monte Carlo mai lamba 15 ta NAPA Auto Parts, Waltrip ya tuka Earnhardt a cikin Busch Series a cikin 1989 da 1994. A tserensa na farko tare da tawagar,
2001 Daytona 500, Waltrip ya karya layinsa na tseren gasar cin kofin 462 a jere ba tare da nasara ba kuma ya lashe tseren gasar cin kofinsa na farko. Abokin aikinsa Dale Earnhardt Jr. ya gama na biyu. Duk da haka, nasarar da kanta ta kasance a cikin duhu ta hanyar Earnhardt, Sr. ta haɗari mai haɗari a zagaye na karshe. A cikin fim din "Ranar: Tunawa da Dale Earnhardt", Waltrip ya ce Earnhardt ya bar shi a cikin layi a ƙarshen tseren, wanda ya ba shi damar jagoranci, yana mai cewa Earnhardt "bai taɓa barin kowa a layi ba". Wannan wataƙila saboda Earnhardt yana son Waltrip da Earnhardt Jr. su gama a cikin Top 2 spots, kamar yadda dukansu membobin ƙungiyarsa ne. Waltrip bai san tsananin hatsarin Earnhardt ba har sai da minti 30 bayan karshen tseren lokacin da yake murna a cikin nasara. Ken Schrader, bayan da aka kula da shi kuma aka sake shi daga cibiyar kulawa ta cikin gida bayan hadarin (mota ya buga ta Earnhardt a lokacin hadarin), ya sanar da Waltrip cewa an kai Earnhardt zuwa Cibiyar Kiwon Lafiya ta Halifax, daga hanyar gudu, inda aka bayyana Earnhardt ya mutu a 5:16 PM EST.