Road freight transport contributes to a large portion of greenhouse gas (GHG) emissions. Transitioning diesel to battery electric (BE) trucks is an attractive sustainability solution. To evaluate the BE transition in New Zealand (NZ), this study analysed the life-cycle GHG emissions and total cost of ownership (TCO) of diesel and BE trucks based on real industry data. The freight pickup and delivery (PUD) operations were simulated by a discrete-event simulation (DES) model. Spreadsheet models were constructed for life-cycle assessment (LCA) and TCO for a truck operational lifetime of 10 years (first owner), this being the typical usage of a tier-one freight company in New Zealand (NZ). The whole-of-life emissions from the diesel and BE trucks are 717,641 kg and 62,466 kg CO2e, respectively. For the use phase (first owner), the emissions are 686,754 kg and 8714 kg CO2e, respectively; i.e., the BE is 1.27% of the diesel truck. The TCO results are 528,124 NZ dollars (NZD) and 529,573 NZD (as of 2022), respectively. The battery price and road user charge are the most sensitive variables for the BE truck. BE truck transitions are explored for freight companies, customers, and the government. For the purchase of BE trucks, the break-even point is about 9.5 years, and straight-line depreciation increases freight costs by 8.3%. Government subsidy options are evaluated. The cost of emission credits on the emissions trading scheme (ETS) is not expected to drive the transition. An integrated model is created for DES freight logistics, LCA emissions, and TCO costs supported by real industry data. This allows a close examination of the transition economics.