But doesn't it always?
For the third time in four years, Holmes' path to a Class 3A state championship is blocked by the No. 1 team in the state, Melbourne Florida Air Academy.
As a freshman, Holmes was on the losing end of a 72-38 drubbing in the region semifinals. As a junior, he almost led his team to the upset of the prep basketball season before his Barons fell 64-59 in the state semifinals.
As a senior?
"Man, I've been thinking about this game for awhile," said Holmes, an FSU signee. "I wasn't trying to overlook districts or anything, but this is the game. This is my senior year and I want to win a state title bad. We're ready."
Tonight at 7, the teams tangle again, at Melbourne Central Catholic with a spot in the region final on the line.
Last year, the Barons (25-3) were overwhelming underdogs. This year, Florida Air (22-1) is more human. The Falcons lost 30-point scorer Walter Hodge (who had 26 against SPC) to the University of Florida, and even lost once this season, snapping a 51-game win streak.
Even Florida Air's 90-29 victory in the region quarterfinals, and junior guard James Burgos' return from injury, isn't enough to shake the Barons' confidence.
"I'm real confident," Holmes said. "We're not going in there like "Man, Florida Air is loaded.' I mean, they're a good team. But I think we're loaded this year."
Holmes is so serious about his final grasp at a state title that he's willing to go scoreless, as long as Florida Air's Evka Baniulis does as well. Baniulis, a 6-foot-7 3-point specialist, has signed with South Carolina and is one of the state's best shooters.
At 6-5 but a world quicker, Holmes has long prided himself on his defense, though it is often overlooked because he has led Pinellas County in scoring the past two seasons. Holmes aside, the No. 3 Barons - who haven't lost to a 3A team all season - have been able to rely on a supporting cast that is contributing in bigger ways this season.
Though a concern of coach Mike Moran's at the beginning of the season, Holmes and Co. might be better this time around.
Point guard Grady Jorgenson, who had one of the best games of his career against Florida Air last year and held Hodge in check most of the game, is heating up and center Ed Rolax gives the Barons a more offensive-minded center. Others, like Noah Cumby, Jock Sanders and David Brett, have the experience of last year's state semifinals.
All of that is enough to convince Holmes he will be graduating with a state championship trophy. That sure would beat having to live with the fact that Florida Air ended your dream three times.
"Trust me, I'm not going to have to worry about that," Holmes said. "We're going to win this game."