For a small market team, the Cleveland Cavaliers have enjoyed much success since their 1970 debut. Many All-Stars and great role players have joined the franchise and left the franchise, but many have also given the fanbase unforgettable "what if" questions.
Whether a failed trade rumor, years-long pursuits or just a missed opportunity to capitalize on a star talent, the Cavaliers' history could have been drastically different if only a few moments turned out differently. For every LeBron James or Donovan Mitchell that the Cavs manage to employ, two or three talents pass through Cleveland's fingers.
Over the years, the Cavaliers have stayed relatively quiet during most of their trade negotiations. While the league's biggest markets tend to negotiate through the media, most of Cleveland's rumors only emerge from reputable sources when actual conversations are had. Thus, when a player enters the Cavs' mythos only to dissipate without anything happening, it is just as important of a news story as the moments when a new player dawns the wine and gold.
Three players of the 21st century stand out as the most prominent players who nearly were Cavaliers but never quite made it to The Land.
No. 1 - Cam Johnson
Most recently, the Cavaliers pursued Cameron Johnson seemingly every offseason and trade deadline. Johnson, with the Brooklyn Nets at the time, is far from an All-Star candidate but was a perfectly suited piece to add to the Cavs roster. The marksman forward was lauded as the ideal addition to Cleveland's frontcourt rotation, becoming a bench sniper alongside Evan Mobley or Jarrett Allen.
Shooting 39 percent from three-point range at high volume over his six-year career, Johnson appeared like a game changer if he joined Cleveland. The Cavaliers chased a 3-and-D wing to complement the core four. Johnson, a 6-foot-8 combo forward, would have slotted in at either small or power forward.
Unfortunately, Brooklyn's asking price continually exceeded what the Cavaliers could offer. For all of Johnson's talent, his high price tag and the Nets' insistence on extra draft capital took the Cavs out of the running. Eventually, Johnson joined Nikola Jokic and the Denver Nuggets in exchange for Michael Porter, Jr. and a 2032 first-round pick.
Though the 29-year-old veteran could still be a trade candidate for the Cavs in the future, his arrival to a proven contender and recent champion likely removes him from the market for the foreseeable future.
No. 2 - Amar'e Stoudemire
In a much more consequential what-could-have-been trade, the Cavaliers' first stint with LeBron included a trade deadline chase for Phoenix Suns All-Star Amar'e Stoudemire. In James' final year during his first run with Cleveland, the Cavs wanted to make a final all-in deal to build a contender around the young superstar in an effort to convince him to re-sign.
The prior season in 2008-09, Stoudemire earned his fourth All-Star nod, averaging 21.4 points, 8.1 rebounds and 1.1 blocks per game. He was an athletic phenom, blowing past any defender and holding down the paint on the other end of the court. Ahead of the 2009-10 trade deadline, Stoudemire had continued his frontcourt dominance as the sidekick to Hall of Fame point guard Steve Nash.
While the deal was nearly completed in mid-February 2010, the Suns and Cavs pulled out of the trade over disagreements on draft compensation. Both franchises were concerned that their respective upcoming free agent stars would leave for nothing but did not want to agree to a poor trade out of fear. In the end, both teams lost the player they sought to retain.
The painful twist of fate pushed the Cavs and Suns off the stage as Finals contenders after years of standing as one of the best teams in their conferences. The Nash-Stoudemire duo had devastated opponents but often fell apart to injuries in the playoffs. As for James, the early Cavaliers nearly achieved the ultimate goal early on before losing to Tim Duncan and the San Antonio Spurs. Without another true star, a young LeBron could not carry the Cavaliers back to the Finals, and the front office never secured a real supporting cast.
No. 1 - Paul George
In what may be the most consequential missed opportunity in modern Cavaliers history, Cleveland was moments away from adding the second-best forward in the Eastern Conference during James' second Cavs era. With the Indiana Pacers at the time, Paul George was an elite two-way wing, becoming the franchise player for a midwestern rival.
After Kyrie Irving requested a trade late in the 2017 offseason, the Cavaliers looked for a reliable star to continue Cleveland's Finals campaigns. Irving was asking out just one year after the historic 2016 run, but the Cavaliers were not ready to pivot to a rebuild yet. George had proven himself against the Cavs multiple times in highly contested playoff battles, and as he entered his prime, he could have been the perfect second star for the Cavaliers.
In a three-team trade, George would have joined the Cavs while Irving joined the Suns. The Pacers would have received a king's ransom in return. All parties were aligned until Phoenix suddenly backed out. The trade died as the Cavs and Pacers could not find a replacement team, and Cleveland eventually pivoted to sending Irving to the Boston Celtics in what became one of the most regrettable deals in franchise history.
Instead of building a formidable eastern dynasty, the Cavaliers watched James leave again the following summer, this time for the sunny beaches on the West Coast with the Los Angeles Lakers.
The Cleveland Cavaliers always find ways to return to contention after short rebuilds, but that does not make them immune to regrettable missed opportunities. Stoudemire could have joined Cleveland for an extra draft pick the Cavs did not want to include, but his arrival would not have guaranteed the Cavaliers anything beyond a talented but underachieving star with potential. There is no way of knowing what results any of these moves would have given the Cavaliers, but it still stings to know what could have been.