Because the Cavs organization sucked.
Let’s face it, some organizations are just not run as well as others. The Lakers under Jerry Buss, Celtics under Red Auerbach, Pop era Spurs and Kerr era Warriors are some of the best managed organizations and they were always able to draft and trade for good talent to help their developing stars.
But then when you look at teams like the Timberwolves, Hornets, Knicks and Kings, it’s obvious that their front office and ownership has issues. They either are not good at scouting players (Kings), overpay for aging stars (Knicks), or are incompetent at getting help for their stars (KG/Love Timberwolves, Lebron Cavs).
I mean, let’s break down how all the top 10 players got help from their organization
Jordan – started off with a badly run Bulls organization, but under Jerry Krause and later Phil Jackson, the Bulls became very competent at developing their stars. The Jordan era Bulls were notoriously stingy with money and they were very reluctant to trade or acquire big name stars. Grant, Pippen and Toni Kukoc were drafted and developed very well by the Bulls organization. The Bulls got Ron Harper as a free agent and basically got Dennis Rodman for virtually nothing from the Spurs, who were intent on getting rid of him ASAP.
Kareem/Magic – first of all, the Bucks got incredibly lucky getting Kareem from a coin flip. Had the coin flip went the other way, the Suns would have drafted Kareem. The Bucks then fleeced the Royals to get Oscar Robertson. They sent 2 no name players to them basically for Big O. Then they drafted another future Hall of Famer in Bob Dandridge. Kareem then gets traded to the Lakers, which at that time was run by Jack Kent Cooke. The Lakers org at that time wasn’t doing too well, but they signed future HoFer Jamaal Wilkes as a free agent, drafted Michael Cooper and then luckily got Magic Johnson from the pick that the New Orleans Jazz originally gave the Lakers in exchange for Gail Goodrich. James Worthy came via another pick they had gotten from the Cavs in exchange for Don Ford. The fact that the Lakers had the #1 pick despite being winning the championship that season is kind of bonkers. They also acquired Bob McAdoo for virtually nothing because at that point he had been bouncing around various teams.
Wilt – Wilt started off on a team that was a few years removed from their last championship and coached by HoFer Neil Johnston. The Warriors didn’t give him too much help until they drafted Nate Thurmond in 1963. The Warriors ran into financial issues and were forced to trade him to the 76ers, which already had a great team with guys like Chet Walker, Hal Greer and Billy Cunningham, and a HoF coach in Alex Hannum. Wilt then pretty much forced his way to LA, claiming that he wanted the bright lights of LA and the chance to date white women, so 76ers had to deal him to the Lakers for basically nothing in return. Wilt was again on a great team with Jerry West, Elgin Baylor already there, Gail Goodrich later re-joining the Lakers a few years later, and HoFer Bill Sharman as coach.
Russell/Bird – Both of these guys benefitted from having one of the greatest executives ever in Red Auerbach. Red first of all got Russell’s pick from the St Louis Hawks, giving them Ed Macauley and Cliff Hagan in exchange, both Hofers but obviously the Celtics won this trade. The Celtics already had a HoF backcourt in Bill Sharman and Bob Cousy, in addition to HoFer Frank Ramsey when Russell was drafted. Incredibly, the Celtics would then go on to draft Tom Heinsohn in the same draft and then Sam Jones in the next draft. A few years later, they draft John Havlicek as well. Red later also traded for Bailey Howell from the Bullets. What an incredible eye Red had for talent! For Bird it’s a similar story. He was drafted by Red and came to a team with Tiny Archibald, Cedric Maxwell and Dave Cowens already present. Red then engineered a trade for Robert Parish and drafted Kevin McHale. Red later engineered another trade for Dennis Johnson. So basically.. Red Auerbach. Yeah.
Kobe – Kobe was drafted essentially by the Hornets in order to trade to the Lakers, a move engineered by another all time great executive, Jerry West. Shaq already signed with the Lakers as a free agent. Eddie Jones and Nick Van Exel already there as well. So Kobe arrived on a team with 3 other all-stars essentially. Then Phil Jackson joins a few years later. Add a few more key role players and there’s the 3-peat dynasty essentially. After Shaq was traded by the Lakers, the Lakers got back Lamar Odom and not much else so the Lakers couldn’t give Kobe much else, but then a series of incredible things happened.. first they draft Andrew Bynum who would later develop into a very solid role player for them, Odom was already solid to begin with, Phil Jackson comes back to coach again, they get Trevor Ariza via trade, but then they somehow managed to fleece the Grizzlies a few years later by trading Kwame Brown to them for Pau Gasol! That was the key to the Lakers winning again. Then the next year after they win, they sign Metta World Peace and that helps them 2-peat.
Duncan – Duncan was drafted to the Spurs by a pretty miraculous event.. The Spurs were actualy already a team good enough to get to the 2nd round but David Robinson had gotten injured and the Spurs basically ‘tanked’ and then got the first pick in the 1997 draft, which they then used on Duncan. Of course Greg Poppovich also turned out to be one of the greatest coaches ever. So Duncan arrived on a team that was already pretty good with David Robinson, Avery Johnson, Sean Elliot already there. Within 2 years of him joining they win. Then over the next decade somehow the Spurs managed to dig gems out of deep draft picks. Tony Parker and Manu Ginobili were both picked very late in the draft and Spurs developed them into future HoFers. They signed Bruce Bowen, a key part of their defense. The Spurs somehow recognized the potential of Kawhi Leonard and managed to convince the Pacers to draft Kawhi to trade to them. They were also really great at recognizing international talent in general.
Hakeem – Hakeem was drafted by a Rockets org who already had a #1 pick the previous year in Ralph Sampson. Adding Hakeem made the Rockets a championship contender, but after Sampson got injured the org really declined and couldn’t give Hakeem many good pieces after that. Notably they got Otis Thorpe via trade, Drexler via trade, and add to that some solid role players like Kenny Smith, Vernon Maxwell and Mario Elie there you have the pieces for a 2-peat.
So there’s the other top 10 guys.
tldr; Jordan – Bulls were great at developing Grant/Pippen and they got lucky with Rodman. Kareem/Magic – Bucks/Lakers were very lucky with getting the right picks and coin flips. Russell/Bird – Red Auerbach. Nuff said. Wilt – always went to teams that had hof players aleady. Kobe – Jerry West, Shaq, Phil Jackson and some nice trades. Duncan – Spurs were great at developing international talent, lucked out with Robinson getting injured. Hakeem – not as lucky or great an org as the above ones, but they gave him enough pieces to win.
So what about Lebron?
Compared to all other top 10 players, Lebron uniquely started out at a Cavs org that was straight up mis-managed and incompetent. Zydrunas and Larry Hughes were simply not good enough. The best they could do is give him a very old Shaq and a very old Ben Wallace. Despite this half assed help, Lebron still took the team to the Finals. But after 7 years he got impatient with the org and finally left.