2) Dwyane Wade and Penny Hardaway
From 1993–94 to 1995–96, Shaquille O'Neal and Penny Hardaway formed one of the most exciting dynamic duos in NBA history. They led the Orlando Magic to the NBA Finals and just their second season together and they appeared to be well on their way to a dynasty. Despite that, Shaq left in free agency in 1996 and Hardaway's career quickly fell apart due to injuries. Shaq then led the Los Angeles Lakers to three straight championships and a fourth NBA Finals before demanding a trade.
He was then dealt to the Miami Heat, where he won another championship with Dwyane Wade. Those Heat teams featured many former NBA stars who wanted to try and win a title, including Hardaway. Actually, Hardaway came out of retirement to play with the Heat during the 2007–08 season and reunited with Shaq and played on the same team as Wade.
Unfortunately for Hardaway, the Heat won just 15 games that season despite being seen as a potential championship contender during the preseason. He retired again after that season without having won a championship, while Shaq was traded to the Phoenix Suns. Given how great he was to start his career, it would have been nice to see Hardaway win a championship with Shaq and even Wade but it wasn't meant to be.