During LeBron James’ first tenure with the Cleveland Cavaliers, the Cavs made the Eastern Conference Finals only once. One of the biggest reasons for the team’s lack of success was that LeBron James was never surrounded with top talent. Even the greatest player of the millennium needs some help.

In 2009-10, his final season with Cleveland the first time around, James’ sidekicks included Mo Williams, 33-year old Antawn Jamison, and 37-year-old Shaquille O’Neal. The Cavaliers fell to the Boston Celtics in the semifinals, 4-2. Unfortunately, that team was Cleveland’s most talented of the decade.

Due to James’ transcendent talent, as well as Cleveland’s poor drafting, the Cavs were unable to add elite, young talent to the team. For instance, in 2001, the Cavs selected DeSagana Diop with the eighth overall pick; in 2002, Dajuan Wagner with pick number six; in 2004, Luke Jackson with the 10th choice. As James quickly developed, the Cavs became too good to have high lottery picks, but not good enough to make the Finals.

Much like the current team, the Cavs were forced to make trades if they wanted to improve their team. But one deal that may have changed the landscape of the entire league never went through.

At the trade deadline during the 2009-10 NBA season, the Cleveland Cavaliers were at a crossroads. They were well on their way to another first-place finish in the East (61-21 would be their final record), and they would contend for a Finals berth. But the team had a larger concern; James was in the final year of his contract. His impending free agency stint would completely reshape the future of the NBA. With a weak roster outside of James, the Cavs would be in deep trouble if he left. An aging O’Neal at the end of his career, and Williams would not be enough to persuade him to remain in Cleveland.

Naturally, a trade would need to be made. James needed help this season, but the team also needed to be prepared if he decided to move on. Young power forward J.J. Hickson had the most potential of the few young players on the roster.

Targets included Wizards power forward Antawn Jamison and Indiana’s Troy Murphy. Both veteran options who would improve the team, but neither was a star who would tip the scales against a team such as the Los Angeles Lakers. However, the Cavaliers did have interest and serious discussions concerning a player who would: Phoenix Suns power forward Amar’e Stoudemire.

Stoudemire was also set to be an unrestricted free agent after the season. He was a perennial 20-plus PPG scorer, who was a physical presence in the post. His defense was nothing to scoff at either. O’Neal and Stoudemire were teammates for the Suns the season before, and pairing the two up with James and Williams would have made Cleveland a force to be reckoned with. A deal would need to include Zydrunas Ilgauskas and his nearly $12 million contract that expired after the season, the Cavs’ first round pick, and J.J. Hickson.

But, the deal fell apart. Maybe it was because the Suns preferred to attempt to re-sign Stoudemire. They failed to do so, and Stoudemire teamed up with Carmelo Anthony in New York. Another reason was that the Cavs wanted to keep their contingency plan in case James left; Hickson. Once hailed as the future of the franchise, Hickson was unable to meet expectations, and was eventually shipped to the Sacramento Kings in exchange for Omri Casspi and a protected first round pick. The current team is in a similar situation; James is a free agent after the 2017-2018 season, and the Cavs, right now, are not able to beat the Golden State Warriors. They own the Brooklyn Nets' 2018 first round pick, which is projected to fall in the top 10. General manager Koby Altman and owner Dan Gilbert will have to decide whether to go all-in on the current team and trade the pick for an established star, or keep it and select a rookie to build around.

The Cavs, after striking out on Stoudemire, pulled off a trade for Jamison, and he ended up being a solid addition to the team. Unfortunately, after the devastating loss to the Celtics, both James and O’Neal signed elsewhere, leaving the Cavs in shambles. The next season, 2010-11, Cleveland set the NBA record for most consecutive losses in a season. The team’s best remaining player, Mo Williams, was traded to the L.A. Clippers for Baron Davis and a first round pick. This trade ended up essentially saving the franchise, as that draft pick ended up winning the lottery, and was used to select point guard Kyrie Irving. Things ended up working out for the Cavs as they won the 2015-16 NBA Finals, but quite a bit of heartache could have been saved had the Stoudemire trade gone through.

After trading Ilgauskas, Cleveland would have had enough cap space to sign both James and Stoudemire to max contracts. Perhaps another marquee free agent would be enticed to join them. Stoudemire would have made the difference against the Celtics, giving the Cavs a Finals berth against the juggernaut Lakers. Maybe they don’t win. Maybe LeBron James still leaves to join his friends in Miami. But the Cavs’ chances of keeping him would have been drastically higher with Stoudemire on the team.