In truth, the Ted Stepien Cleveland Cavaliers have a multitude of regretful trades. So many so that the NBA instituted the “Stepien Rule”, forbidding teams from trading consecutive first round picks.
Stepien traded away so many draft picks for seemingly nothing in return. Numerous picks eventually ended up with potential for NBA legends, such as John Stockton, James Worthy, Charles Barkley, and more.
When the Association invents a rule just to stop your owner from intentionally ruining your franchise, you have a tough history in the trade market. Though teams find plenty of ways around this stipulation, its existence might be the biggest way the Cavaliers have impacted the NBA.
Recent years have been quite different, however. The Cavaliers acquired Kyrie Irving in the 2012 NBA Draft first overall after trading for the Boston Celtics’ first round selection. Recently Donovan Mitchell joined Cleveland’s ranks after a blockbuster trade from the Utah Jazz.
On a smaller scale, the Cavs acquired Caris LeVert in a controversial move, but his production in Cleveland has carved him a substantial role on a developing contender.
The modern Cavaliers are not perfect in their negotiations. Hindsight might show an alternate path Cleveland could have followed, one that might have shaped the team’s overall place in the NBA.
Whether it’s keeping this player altogether or receiving a better deal in return, these three losses to the Cavs still leave the heart wondering what could have been.
The Cleveland Cavaliers losing Andre “The Professor” Miller still stings
While Cleveland faithful had every reason to loathe LeBron James’ decision to take his talents to South Beach in 2010, it is hard to argue that the team around the budding superstar was any sort of contender.
One of the worst decisions made came just before James’ journey began. In summer 2002, the Cavaliers traded a young Andre Miller to the Los Angeles Clippers for Darius Miles, who was traded to Portland later the next season. Miller had just recorded 10.9 assists per game in 2001-02, the most in the NBA.
Trading away one of the best young guards in the NBA was not only a poor choice, but Miller’s fit with the future 2003 first overall pick is one of the greatest “What Ifs” in Cavaliers history.
The GM at the time, Jim Paxson, later admitted that the trade was made with the intent to snag LeBron in the draft (subscription required). Tanking for lottery luck is nothing new in the NBA, but the Miller-led Cavaliers were only 29-53 in that season. Losing The Professor guaranteed better draft odds, but there might have been a better route to tanking to keep Miller and still land LeBron.
Once the Cavs got LeBron, the team was so poorly constructed that they could never find a way to build around him. Having Miller would have changed that.
Building a duo of LeBron James and Andre Miller would have given the Cavaliers a much more competitive roster in the early 2000’s. Instead, the Cavaliers were an embarrassment to the league on how to build around a generational talent. James eventually returned after four years (and two rings) in Miami, leading the Cavaliers to a historic 2016 NBA Finals win.
The potential for LeBron and Miller in Cleveland is a great mystery now. Could the Cavaliers have won the championship with those two at the helm? Guaranteeing a championship is impossible, but the team would have certainly been an exciting one to watch.
The next trade also might have led to more championships in the Land and may have been the start to the rebuild the Cavaliers recently completed.
The Cleveland Cavaliers made the wrong Kyrie Irving trade
In the midst of the 2017-18 season, NBA Champion Kyrie Irving requested a trade out of Cleveland, breaking up the pairing of himself and LeBron.
At the time, Irving felt it was time to step into a leadership role, no longer wanting to play second fiddle to James. Surely, for a player who was undeniably pivotal in the Cavs’ 2016 run, wanting to lead a team is a reasonable desire. Looking back, it was clearly an immature and unnecessary choice. Irving has yet to reach the level of success he found with James and has joined a number of different teams.
In return for Kyrie, the Cavaliers received All-Star point guard Isaiah Thomas, Jae Crowder, Ante Zizic, and a 2018 first round pick that turned into Collin Sexton.
For the era of the trade, this was an exciting package. Cleveland got an All-Star, multiple good role players, and a first round pick. The problem was that Isaiah Thomas was injured and never returned back to his former self.
The Cavaliers returned to the NBA Finals in 2018 but lost in four games to the Golden State Warriors. That summer, LeBron James left for Los Angeles (in a much less dramatic fashion than 2010).
Irving was almost sent to Phoenix, though, instead of Boston. In a three-team deal, the Cavaliers were reportedly close to completing a three-team trade (subscription required) to acquire Paul George and Eric Bledsoe in exchange for Irving.
Paul George at the time was one of Cleveland’s greatest adversaries, earning a reputation as one of the Association’s best two-way forwards, defending the greatest scorers while scoring endlessly himself.
Once again, it is impossible to know what would have been accomplished with George in the Wine and Gold, but the idea of a James, George, and Kevin Love big three is painful to have never witnessed in reality.
Finally, the Cavaliers traded for a superstar but might have rather kept somebody out of the deal.
Losing Lauri Markkanen was a mistake
As part of the Donovan Mitchell trade to Cleveland, the Utah Jazz received 7-foot-tall forward Lauri Markkanen. In the 2021-22 season, Markkanen started for the Cavaliers at the small forward position and helped reshape Cleveland’s image as a competitive team in the Eastern Conference.
The Cavaliers traded Markkanen one year after trading for him from Chicago. in his season with Cleveland, Markkanen averaged 14.8 points on a 35.8 3-point percentage and grabbed 5.7 rebounds per game.
In his first season with Utah, Markkanen earned his first All-Star appearance and averaged a career-high of 25.7 points, shooting 39.2 percent from 3-point range. In addition, Markkanen’s rebounding went up to 8.6 per game, and he won the 2022-23 Most Improved Player award.
This is not to say the Cavs should not have traded for Donovan Mitchell. Mitchell had what was arguably his best season yet in his career with the Cavaliers. He set a single-game franchise record with 71 points versus the Chicago Bulls. Spida Mitchell also was voted to the All-NBA Second Team for the first time in his career.
In a redo, the Cavaliers probably do not offer Markkanen in the deal, though. Cleveland’s worst weakness last season was their poor perimeter presence. Trading other players instead of Markkanen would have given the Cavs the floor spacing so desperately needed.
Keeping Markkanen in the trade likely means parting ways with one or both of Jarrett Allen and Isaac Okoro, two players who have equally helped Cleveland’s recent success. Markkanen would have certainly not had the opportunity to develop as much as he did in Utah, as both Mitchell and Darius Garland would have orchestrated the offense the majority of possessions.
Lauri’s fit in Cleveland would have been perfect, nonetheless. Maybe Utah never accepts a trade without Markkanen. In that case, it’s worth it.
But, in hindsight, Markkanen might be the missing piece for the Cavaliers going forward. Losing that is not easy to ignore.