That doesn't mean they've gotten better at it.
For the second straight year, third time in four years and fourth time since 2003 - when they selected a high school phenom named LeBron James - the Cavs own the No. 1 overall selection. On Thursday night, the Cavs, who only chose new coach David Blatt last week, will once again be the first team on the clock.
They've been lucky. Now, they need to be good.
Cleveland is expected to select either Duke forward Jabari Parker or Kansas forward Andrew Wiggins, considered a pair of can't-miss prospects who could help push the Cavs back to respectability. Either of them could also make their roster more appealing in case James, who opted out of his Miami Heat contract on Tuesday, is thinking about bringing his talents back to his native Ohio after four years - and four straight trips to the finals.
James' decision to hit the free-agent market has Cleveland, and nearly every other NBA team, re-evaluating draft plans. The Cavs are in an interesting predicament: They could overhaul their roster by trading star guard Kyrie Irving or another starter two to create salary-cap space for James and to possibly land another All-Star, but then risk having James break their hearts again and sign elsewhere; They also could make a play for Minnesota's Kevin Love.
One thing is certain, the Cavs have several options at No. 1.
They could work a trade to acquire players or picks. It's possible the Cavs are still intrigued enough with Kansas center Joel Embiid, who recently underwent foot surgery and is expected to be sidelined for six months, to strike a deal, move out of the top spot and select the 7-footer.
Embiid may be raw, but some believe he's also rare, too rare to pass up.
''I still think Joel Embiid, the big guy, is the best prospect in this draft,'' ESPN analyst Jay Bilas said. ''I understand the reticence because of his recent injury, but I would have to have a medical team tell me, `Don't take this guy, this is a bad medical risk' for me to say no to him.''
Cavs general manager David Griffin began receiving calls from teams looking to get their hands on the top pick shortly after Commissioner Adam Silver announced it had fallen in the lottery to Cleveland, a gift sent the club never expected. It will take plenty to pry the choice away from Griffin, who sees it as a chance to speed the team's recovery.
Assuming he hangs onto the choice, Griffin can't afford to miss as badly as the Cavs did a year ago, when the team's surprising selection of UNLV power forward Anthony Bennett at No. 1 backfired. Bennett arrived at training camp out of shape following shoulder surgery and never got his weight or game under control. He missed his first 16 shots, averaged just 4.2 points and 3.0 rebounds in 52 games and became emblematic of the Cavs' season: A huge disappointment.
To Bilas, that would mean Parker, who worked out for Cleveland last week.
''He's NBA ready on the offensive end right now,'' Bilas said of the 6-foot-8, 240-pounder, who became the first freshman to lead the Blue Devils in scoring and rebounding.
Wiggins, though, may wind up being the better player. A freakish jumper, the 6-8 Wiggins has been projected as this year's top pick since last year's draft ended. In fact, if he had been eligible, Wiggins, whose father Mitchell played in the NBA, would have probably been the No. 1 pick in 2013.
He averaged 17.1 points, 5.9 rebounds and accepted his role in the Jayhawks' system. But Wiggins had a tendency to disappear in big games, most jarringly in the NCAA tournament, when he scored just four points on 1-of-6 shooting as Kansas was eliminated by Stanford.
Bilas said if there's a knock on Wiggins, it's that he may not be ready to carry a team.
''Is he going to be the type of guy who is going to lead your team and be the best player on the floor?'' Bilas said. ''Does he have the burning desire to do that? I think that's still an open question with him. But athletically, he's the guy. I would take Wiggins if Embiid was out of the picture, but Parker's safer.''
The Cavs have choices, now they have to make the right one.