4. Milwaukee Bucks
Trade proposal:
Bucks receive: Jimmy Butler
Heat receive: Damian Lillard
Former Portland Trailblazer point guard Damian Lillard was set on joining the Heat, specifically to team up with Jimmy Butler and Bam Adebayo under the leadership of Pat Riley and Erik Spoelstra. However, that didn't happen, and the desire for this trade was not as mutual between Lillard and the Heat as it seemed. Maybe things would happen differently, but this time it would be between Miami and the Milwaukee Bucks. What if the trade proposal was the Heat trade Butler to the Bucks for Lillard?
In 2018, the Bucks were desperate for an NBA championship title, so they reached out to their superstar, Giannis Antetokounmpo to ask for his blessing on the opportunity to acquire All-Star wing player Jimmy Butler from the Minnesota Timberwolves.
Giannis' influence on the Milwaukee Bucks organization was strong, as he advised against the idea of trading for Butler from the Timberwolves. Jimmy ended up being traded to the Philadelphia 76ers in a deal involving three other teams. Antetokounmpo preferred to stay loyal and keep teammate Khris Middleton on the team.
After a whirlwind of trade talks and disappointment, Lillard who was acquired by the Bucks last season, seems to be fitting in seamlessly. Fast forward to 2023, Middleton and Antetokounmpo, along with Dame have formed a formidable trio that is highly regarded in the league. Despite past losses to Butler and the Heat, the Bucks are focused on maximizing Antetokounmpo's time in Milwaukee with the addition of Lillard. The future success of Giannis and Middleton together remains to be seen, but it seems that Giannis has no regrets about his decision in 2019 to not be paired with Butler.
Giannis' decision is seen by some as a significant missed opportunity for the team, but is it? At the time, the superstar chose to stay with Middleton, and the team missed their chance to add star power. The Heat are currently lacking All-Star caliber players alongside Butler, Herro, and Bam Adebayo.
It may be safe to say that the Heat missed out on acquiring Damian Lillard as the Bucks did so with Jimmy Butler. Miami would have greatly benefited from Lillard's scoring and playmaking abilities, especially during crucial moments in the playoffs, like the series against the Denver Nuggets in the NBA Finals. The Heat has reached the Finals twice in the last four seasons, showcasing the coaching prowess of Spoelstra and the strong front office led by Pat Riley, Andy Elisburg, and Adam Simon.
While Butler may not have been on the same level as Lillard at the time, had he teamed up with Antetokounmpo in 2018, it is likely that he would have re-signed with the Bucks, and they could have potentially become champions multiple times by now. At the very least, the Bucks may not have suffered defeat against the Heat last summer. It's hard not to wonder what could have been if Butler had joined the Bucks instead of the 76ers all those years ago. As for Jimmy, he remains determined to win an NBA championship with Miami.
Due to NBA regulations, Miami cannot trade first-round draft picks until 2028 and 2030. If the proposed deal for Lillard was still a reality, it would revolve around draft picks and other players including Tyler Herro. This proposal isn't straightforward or feasible without a third or fourth team looking to be involved, which is common in superstar trades.
Lillard would be unable to be acquired by Miami directly because of salary-cap regulations, and the Bucks would need to include more salary in the deal to land Butler due to the state of his contract. The inclusion of extra players in the offer would also make this wild trade scenario significantly disadvantageous for both organizations, but more so for the Heat at this time. Miami needs a regular season All-Star not just in the playoffs. If Butler left Miami and added Lillard to the roster, the team's chances of competing for another title would be tough, as we know one best player is not enough. It takes a team to win.