In fact, the list of players who have left but can't stay away is lengthy. When arguably the game's all-time greatest player, Michael Jordan, does it twice, that just about removes any negative stigma.
But Roy's retirement was different. After just five seasons (and three All-Star Game appearances), the then 27-year-old cited ongoing knee injuries as the main reason behind his decision.
So this wasn't another good player struggling to accept that Father Time had once again relegated a former star to a reserve role. Those knee issues had gotten so bad so quickly that Roy's production dropped from 21.5 points in 37.2 minutes in 2009-10 to just 12.2 points in 27.9 minutes the following season.
One of the NBA's greatest guys away from the court (and most exciting players on it) had his career cut strikingly short. So please, forgive the cheers you may have heard from the press box when the Minnesota Timberwolves signed Roy over the summer.
Expectations were cautiously optimistic for what his knees would allow him to accomplish. And they were far more cautious than optimistic.
But with all of the questions surrounding his return, there was one question that necessitated it. Roy told The Oregonian's Jason Quick that he couldn't live with his lingering thoughts over whether or not he left the game too soon.
Maybe he watched too much game film from his three-year stretch of at least 19.1 points, 4.7 assists and 4.4 rebounds. Or maybe he just couldn't figure out which direction he wanted to take his life.
Whatever the reasoning, Roy decided that leaving the game on his own terms was something that he hadn't been able to do the first time around and needed to do for himself and his family.
The basketball gods owed this return to Roy and the NBA fans. This was bigger than the fact that his addition helped Minnesota enjoy a rare appearance among basketball's sleepers. It was bigger than the sport itself.
This was the chance for Roy to, at best, rediscover his mastery of the NBA hardwood (even on a limited basis) or, at worst, find some closure to this chapter of his life. For the fans, it also brought the chance to say thanks for that incredible four-year run that transformed Portland from the punchline "Jail Blazers" to a Western Conference powerhouse.
But even as important as this comeback has been, it's still part of one basketball's biggest tragedies.
In a time of one-and-dones and teenage phenoms, Roy gave the Washington Huskies four years of production. He gave the Trail Blazers leadership, production and a barrage of clutch baskets. He brought those same leadership qualities to Minnesota and as much production as his body allowed.
But that's the thing. His body's already costing him more games.
Friday night was supposed to mark his return to the Rose Garden. Instead, arthroscopic knee surgery is expected to keep him sidelined for at least a month, according to Ray Richardson of the Pioneer Press.
No one knows where this comeback will take him. It's just unfortunate that it had to happen in the first place.