Following the 1997 racing season, Roush Racing withdrew from Trans-Am competition and shifted its attention to NASCAR sanctioned series, mainly the newly formed Roush Racing Craftsman Truck Series team. Late in 1997, Jack Roush and Tommy Kendall were in negotiations to bring Kendall to NASCAR, beginning with the 1998 Craftsman Truck Series season. According to various sources, Kendall was close to signing a four-year deal with Roush, however Roush shortly afterward informed TK that the terms of the contract had changed. Kendall objected at first, but after some time ultimately agreed to the changes. By that time Roush had already hired Greg Biffle to fill the seat. Later comments from Jack Roush indicate that the biggest obstacle between the two men and the completion of the deal was geography.
    ”The fact of the matter was, he [Kendall] wanted to live in California and have a career in stock-car racing, and that’s fundamentally wrong. I would not support that, I would not be a part of it. I wasn’t going to suffer the frustration, I wasn’t going to suffer the embarrassment to the sponsor.”
    In January 1998 Kendall was in negotiations to drive the #27 David Blair Ford entry in the NASCAR Winston Cup series, however those talks stalled when no sponsor was found. A full-time ride in the Busch Grand National circuit was another possibility that ultimately didn’t come together.