In Cleveland, the “what if” conversation has a way of circling back to injuries, bad timing, and the kind of draft swings that never quite landed. Put those names together and you get a roster full of talent that flashed, broke down, or never got the runway it needed.
Isaiah Thomas is one of the clearest examples. With Boston from 2015-2017, he was one of the league’s most electric scorers - buckets, clutch shots, and even a 53-point playoff performance from a 5 '9 guard who was the final pick of his draft earlier in 2010’s.
But by the time he arrived in Cleveland as the centerpiece of the Kyrie Irving trade, his hip had already betrayed him in the postseason. He was nowhere near the same player with the Cavs, appeared in just 15 games, and was dealt again at the 2018 trade deadline.
Cleveland got the same number of games from Baron Davis, by the way.
Dajuan Wagner belongs in that same painful category. At Memphis, he averaged 21 points per game in his lone season and came off as fearless, a shot-taker with real lottery-pick buzz.
Cleveland thought it had a potential difference-maker. Instead, he managed only 102 games over three seasons, and his efficiency never matched the promise.
He played one game with Golden State in 2006-07 and was out of the league at 23. For a team that had already missed on Wagner and later lost Carlos Boozer after just two seasons, that was a brutal stretch.
Luke Jackson was another high-upside swing that never really got going. At Oregon, he put up 21-7-5 per game on 49% shooting by the time he graduated, a big, skilled playmaker who looked ready to help right away.
The back problems changed everything. He played 10 games as a rookie and 36 as a sophomore, and that was basically the end of his Cleveland run.
Taken #10 one year after LeBron James, he was supposed to fit alongside him. Instead, his NBA career ended up lasting just 73 games across five teams.
Then there’s Anthony Bennett, the pick everyone remembers. Cleveland won the 2013 lottery and took him #1 out of UNLV in a draft without a true consensus top choice.
Plenty of people had Nerlens Noel in the conversation, even with his first year expected to be lost, but the Cavs went in another direction and selected a player many believed wouldn’t have gone top ten otherwise. Bennett dealt with sleeping issues and weight problems, had only a few decent games as a rookie, and was later included with 2014 top pick Andrew Wiggins in the deal for Kevin Love.
Four seasons, four teams, and that was it. He’s still only 33, and he remains in the conversation as the worst number one overall pick in NBA history.
Anderson Varejao is the outlier here because he actually had a real run in Cleveland, but he still fits the theme. He was an important role player during LeBron James’ first stint, then his body started failing him just when the Cavs needed more.
Over three straight years, he missed 51, 41, and 57 games, even while being listed as the starting center. He played a smaller role in 2013-14 and managed 65 games that season, but the injury problems returned after James came back.
He was traded at the following deadline. If he’d stayed healthy, maybe Cleveland wins more games and maybe his game keeps growing.
That’s part of why Timofey Mozgov even enters the picture in 2014-15. Before going down in 2012-13, Varejao had been averaging 14 points and 14 rebounds per game and looked like he was on his way to becoming an even bigger piece.
The list gets even messier from there. DeSagana Diop, a 2002 first-round pick, was never productive.
The Derrick Rose experiment didn’t work in Cleveland. Kevin Love’s arm was ripped out of its socket.
And 2015, as the source puts it, could have ended differently.
In Other News...
Kevin Love Brought Back A Cavs-Raptors Joke Toronto Still Hates
Kevin Love showed up in Toronto for Kyle Lowrys jersey retirement celebration and immediately nudged an old playoff wound back into the conversation. With former Raptors teammates around and Toronto Mayor Olivia Chow presenting Lowry with the Key to the City, the night was built around honoring one of the franchises defining players, while the Raptors also announced that Lowrys No. 7 will be retired on Jan. 10, 2027.
Love, of course, could not resist leaning into the Cavaliers-Raptors history that still lingers for both fan bases, jokingly using the word LeBronto in reference to those postseason clashes. It was a light bit of nostalgia in the middle of a bigger celebration, but it also served as a reminder that even in a tribute setting, the old rivalry can still get a reaction north of the border. [Read more 🡒]
Cavs Double Down On Continuity With A Front Office Decision
The Cavaliers made a clear choice to keep their organizational structure intact, promoting Brandon Weems to general manager as they continue building around their key players. It is the kind of front-office move that signals confidence in the direction already in place, valuing familiarity and internal growth as much as a splashier outside search.
For Cleveland, continuity matters because the roster is still very much in the window where the right decisions around the margins can shape the bigger picture. Weems steps into a job where every move carries weight, from preserving what works to helping guide the next phase of the teams development, and the real question now is how that stability will show up when the Cavs start making their next major basketball decisions. [Read more 🡒]