[Retiring in 1998 seemed like a pretty good choice for Jordan.
Even though that year's championship still went to the Portland Trail Blazers, Jordan, like the unfortunate Jerry West, could never defeat Bill Russell in the Finals.
But Jordan still managed to seize the opportunity to win three championships, own the world's most famous sneaker brand, amass a fortune in US Dollars, have a private jet, and enough financial resources and energy to explore his greater passion for baseball and golf.
But was such a career really enough for Jordan?
Especially when Ah Gan won the championship again in 1999 and 2000, completing a third three-peat and achieving an unprecedented feat.
A ten-time champion, an unmatched status as the greatest in history, the topic of who was better between Gan and Jordan quietly disappeared without any debate.
So, did Jordan ever consider making a comeback during his retirement years?
Clearly, Jordan did, but his pride wouldn't allow him to join any championship-level team to directly challenge Ah Gan and the Portland Trail Blazers.
In 1999, he had the opportunity to join the New Jersey Nets and team up with Charles Barkley and Olajuwon. With him on board, the Nets would likely replace the New York Knicks to challenge Ah Gan in the Finals.
But Michael refused the checkbook waved by Microsoft mogul Paul Allen, preferring to retire directly rather than form a superteam just to get a ring.
Later, Phil Jackson and the Lakers also extended an olive branch to him, offering the chance to team up with Pippen again for another championship in the 2000-2001 season.
But he still refused, not wanting to collaborate with Phil Jackson again.
Michael always insisted that the process was more important than the result. Although people can be easily swept away by the sweetness of success, one's perspective on the process determines their true stature.
Michael practiced this principle, as the fractured Bulls were no longer a team he wished to fight for. After leaving the Bulls, his relationship with Phil Jackson swiftly collapsed.
He realized that Jackson had been manipulating him all along, using his competitiveness to unify the team for victories.
Although interactions between people inevitably involve some level of mutual use, Jordan always believed that true friendship involved genuine affection and appreciation devoid of selfish motives, which is why he increasingly valued his friendship with Ah Gan and Barkley.
He and Barkley, along with Ah Gan, invested in some ventures together and often played golf and bowling during the summer.
At the 2000 Olympics, both Jordan and Barkley stated that if Ah Gan could win the Olympic championship, they would be equally happy for him.
Barkley landed a commentary job at Turner Television, reportedly thanks to Ah Gan, with both the contract duration and amount being substantial.
Jordan, however, reaped considerable gains from several foreign trade investments, as the trade channels Ah Gan possessed in China were practically money-printing machines, though Jordan himself wasn't very keen on them and preferred to refer friends instead.
Meanwhile, Jordan's relationship with his family became increasingly strained, showing no signs of improvement.
His sister Sis was still engaged in an inner struggle of grief after their father's death. She began writing a book shortly after Old Joe's passing in 1993, only to abandon it in 1995.
She's always criticized her brother Jordan for spending a fortune on gambling, even though Jordan never financially neglected the family.
He always provided them with money, over 100,000 US Dollars a year, but his sister claimed she didn't want to push the responsibility of raising her children onto Michael, and everyone disliked Jordan's extravagant spending at casinos and his rampant purchase of luxury goods.
After receiving criticism, Jordan immediately gifted each family member a brand-new car, courtesy of a local North Carolina dealer. But he gave his sister a used Pathfinder, prompting her criticism about him using wealth to control the family.
From then on, Jordan stopped contacting his sister. Upon hearing that she intended to publish an autobiography after his retirement, Jordan expressed anger, vowing never to buy or read the book.
His relationship with his mother, Deloris, also grew distant, with Deloris publicly criticizing Jordan for not being kind enough to his family, and Jordan choosing to refuse donations to the James Jordan Center.
Aside from the inherent complexity of family relationships, it's evident that Jordan is breaking free, or has already broken free from the nest of kinship, love, and family that nurtured him during his youth. This nest bred him, gave him strength, but eventually, he'd have to leave it. He had become too big and needed to soar to further distances.
By the year 2000, two years into retirement, Jordan was actually only 37 years old, at what should have been a peak career stage from a societal standpoint, but as an athlete, he was entering the final stages.
Off the court, Jordan was an exceptionally successful businessman. According to a survey, as much as 90% of NBA players declare bankruptcy within a few years of retiring.
Many of them are deceived by agents and fund managers, entirely exploited, while others fall victim to the education system, receiving little to no financial education. Most are clueless about money management.
When they leave the league, they can no longer maintain their once-luxurious lifestyles.
Jordan, on the other hand, maintained a long-term partnership with Nike, and the Air Jordan brand alone keeps him wealthy for life. Not to mention, his various off-court investments have all yielded substantial returns, making him a bona fide billionaire.