Maybe he was blinded by the tradition that was left in the rearview mirror four years earlier. Or perhaps it because at 31 years old and never having been a head coach at any level, Kiffin couldn't possibly have know what he was in for.
As it turned out, the job was far bigger than Kiffin imagined.
The Raiders went 4-12 in Kiffin's first season, better than the 2-14 the previous year under Art Shell, but falling in line with the 4-12s that cost both Bill Callahan and Norv Turner their jobs.
This year, anyway, Kiffin has no such concerns. When he met with the media for the last time in 2007 to talk about the future, it was with the confidence he would return.
There wasn't as much progress in terms of wins as Kiffin had hoped. The Raiders are 19-61 over the past five seasons since winning the AFC title in 2002 -- all of which have double-digits in the loss column.
No other team in football has lost as consistently over that span.
When asked if he had underestimated what the four years of losing had done to the organization prior to his arrival, Kiffin conceded that was the case.
"It's a difficult mentality to have when people are so used to losing it's just what they know," Kiffin said. "It's what happens. You lose games. You find a way to lose them. It is more difficult than if a team had just one year of it. With a team that we have that's pretty young, that's all that some of them know."
Kiffin, a former co-offensive coordinator at USC, agreed it was his longest season -- and not because of the length of the schedule.
"It didn't seem long because of the amount of work or the weeks but because we kept losing," Kiffin said. "That will make it long -- especially because I have been fortunate enough to lose eight games over the past five seasons. So when lose 12, and two in the preseason -- that's 14 losses -- that makes for a long time."
So where did Kiffin see progress in his rookie season?
By hiring Tom Cable as line coach, starting three new linemen and moving two others from the positions they played in 2006, and switching from man blocking to a zone scheme, the Raiders had their best rushing season since 2000 -- averaging 130.4 yards per game.
Justin Fargas, who was no lock to even make the team out of training camp, won the starting job just before the midway point of the season and rushed for 1,009 yards despite missing the last two games due to injury.
It laid a foundation that will help in the development of JaMarcus Russell, the No. 1 overall draft pick who didn't sign a contract until early September and didn't see any meaningful playing time until the last two weeks of the season.
"Until you have all the things in place that you need, you need to run the football," Kiffin said. "As a young team coming together with a young quarterback, you need to do that. I think that will go a long way for us and a long way in the development of JaMarcus."
The defense was a different story.
The unit was thought to be the strength of the team after a No. 3 overall ranking in terms of yardage the previous year, but the Raiders dipped to No. 22 in total defense and were 31st in rushing defense, giving up 145.9 yards per game and surrendering more than 100 yards to 10 running backs.
It is expected to cost defensive coordinator Rob Ryan his job, and other defensive staff and personnel changes should be in the offing.
Overall, players seemed to be on board with Kiffin in a way they weren't under Shell and Turner.
Barry Sims, one of the few Raiders who were around for all three division titles from 2000 through 2002, is encouraged about the direction of the team even though he can't be entirely sure it includes him.
"We're moving in the right direction," Sims said. "There's a lot of stuff that's going to change like it does every year. We've just got to regroup, get new guys on board and hopefully we'll make a run."