Looking back at the biggest "What If" trade in recent Cleveland Cavaliers history

2017 NBA Finals - Game Three
2017 NBA Finals - Game Three / Jason Miller/GettyImages
1 of 2

One missed opportunity might have completely changed the trajectory of the Cleveland Cavaliers and their second run with LeBron James.

When the Cavaliers drafted Akron native LeBron James first overall in the 2023 NBA Draft, Cleveland walked away from a decade of being stopped short of the Finals by Michael Jordan and the Chicago Bulls with the greatest prospect the franchise had ever seen. Before LeBron James led the Cavs to the 2007 NBA Finals, the organization could never reach the biggest stage.

In 2010, James left the Cavaliers for the Miami Heat after being knocked out of the playoffs short of the Finals time and time again. Cleveland had remained in NBA purgatory and could not build a winner around their young star. Once James left, the Cavs entered a dark era of the team's history. They tied the longest single-season losing streak ever in the NBA by dropping 26 consecutive games. The only bright spot for Cleveland was another young star in Kyrie Irving, who they had drafted first overall in 2013, but they had not been able to reach the postseason with Irving at the helm.

In 2014, LeBron James returned to Cleveland and led the Cavaliers to four consecutive Finals appearances alongside Irving and Kevin Love. Irving and James quickly formed a league-leading duo over these four years. Irving's playmaking, shooting and clutch mentality paired perfectly with James' all-around dominance. Following the unforgettable and historic 2016 3-1 comeback against the Golden State Warriors, that same partnership began to shift.

Before the start of the 2017-2018 regular season, Irving requested a trade from the Cavaliers. On August 22, 2017, Cleveland agreed to send Kyrie Irving to the Boston Celtics in exchange for Isaiah Thomas, Jae Crowder, Ante Zizic and a 2018 first-round draft pick. Thomas had developed into a star in his own right, leading the Celtics to numerous deep playoff runs in the East over the past years. Crowder and Zizic also gave the Cavs a deeper lineup going into the latter half of the season.

Unfortunately, Thomas' tenure with the Cavs was far from ideal. Thomas began the season recovering from a prior knee injury, and Cleveland posted a 7-10 record upon his January return. By the 2018 trade deadline, tensions rose to new heights on the Cavaliers, and it was clear the pairing was far from what Irving and James had been. Only months after dawning the wine and gold, the Cavs traded Thomas in a trade that seemed to solidify that LeBron James' second run with the Cavaliers would not extend beyond his upcoming free agency.

While the past can never change, the Cleveland Cavaliers were mere moments away from an entirely different timeline. Rather than a botched Kyrie Irving trade, the Cavs almost exchanged the disgruntled star for perennial All-Star.