He's been here before, no longer the youthful coach learning as he goes.
Last season, for all intents and purposes, was a disappointment. Ole Miss, again, failed to reach the NCAA Tournament. Gone are some key members of the team, namely dynamic guard Terrico White.
But for Kennedy and all involved with Rebel basketball, the upcoming 2010-11 season offers a new beginning. And Kennedy likes what he has. Well, at least he does in October.
"Like most every coach, I really like my team in October," he said. "I hope we like them in February and March."
Unlike this time last year, when fans and media alike anxiously awaited the pairing of Chris Warren and White on the same floor for a full season, expectations for Ole Miss aren't high. There's plenty of turnover, undeniable talent gone from a 24-11 team.
Kennedy was encouraged Wednesday. A trio of upperclassmen – Warren, Zach Graham and Trevor Gaskins – will lead a new-look lineup.
Terrance Henry and Nick Williams are valued, workmanlike role players. Reginald Buckner, while just a sophomore, has impressed with his newfound work ethic.
"Excited to get started," Kennedy said. "There's been a lot of talk about the pieces that are no longer here. I'm excited about the pieces that are. The offseason approach has been as good as any team that I've had here.
"It's hard to believe it's going on (year) number five."
Believe it, coach.
This may not be Kennedy's most talented team, but if you ask him, it's his most mature. Team chemistry, or lack of team chemistry, was obvious last season. For all the glitz and glamour, Ole Miss was vastly inconsistent.
"The dynamic of this team is totally different, as you would imagine," Kennedy said. "Of our 12 scholarship guys, six of them are new to this situation. I think we've got a good mix, though. We've got a good mix of the old and the new."
Kennedy has seen a new focus with this team, one he's proud of. By his own admission, he's an early riser. He has kids at home, meaning, as he says, he "gets up by force, not by choice."
When he arrives to work each day, he can't help but overhear the sound of basketballs dribbling on the practice courts near his office. It's something he looks forward to, a simple joy of life as a head coach. Maybe more so because of the significant ups and downs he's faced over four seasons.
As he peers inside, he sees players working, sweating, with disregard for the often monotonous, early-morning hours. It's a renewed dedication. These players are doing extra.
"Guys are bouncing that ball at 6:30 in the morning, in a full sweat, which tells me they've been there a while," he said. "The kids have been very workmanlike in their approach. As a result, I think we'll be able to hit the ground running.
"I think I have a pretty good understanding of their work ethic. I think this is a group that's pretty no-nonsense."
Make no mistake: Ole Miss is led by Chris Warren. Kennedy said he sets the standard, a prolific scorer who stands as one of the leading scorers in school history and in the conference.
"I think a lot of it is new guys come in and immediately figure out what the standard is and what's acceptable and what they can get away with," Kennedy said. "I think the temperament of our guys… they're just a little more mature. They're seeing a seriousness from the staff, but it really takes when it comes from the players.
"We have a group of upperclassmen that we hope can maintain this level of accountability that will bode well for us this year."
There was no ignoring the giant elephant in the room Wednesday. A sense of urgency in reaching the NCAA Tournament, a goal not met in Kennedy's time at Ole Miss, remains. Maybe this is the year. Maybe it's not.
But in October, when Kennedy confesses to liking his team the most, optimism abounds.
"The great thing about this group, I've had a lot of guys in the meetings leading up to our first practice, when I've spent time with them one on one, they all talk about wanting to do it for someone other than themselves. That's a great sign," Kennedy said.