It's a decision that small-market teams hate to face, but it is often an unfortunate reality.
With teams like the Denver Nuggets and Orlando Magic being unable to hold on to one superstar, the Minnesota Timberwolves may be forced to decide which of their two rising stars deserves the most attention.
Now the front office does have a little time to weigh its options. Ricky Rubio is working on his rookie contract for one more season, and Kevin Love's locked up for next season as well.
But they'll need to have their minds up before the summer of 2014 arrives.
That's when Rubio can become a restricted free agent, assuming the team can't secure a long-term contract extension. It's also the time that Love can opt out of his current contract, which may be a mere formality given the hefty pay raise he'd be sure to see.
So which direction should the Minnesota brass be leaning at this point?
Well, there's a case to be made for either side.
Perhaps the most intriguing aspect on Rubio's behalf is that he's only hinted at the type of player he can become. Injuries have limited him to just 90 games in his first season, and he spent some of those outings carrying the obvious effects of his past ailment.
If he maximizes his potential, he's a once-in-a-generation type of talent.
Even with a shooting stroke that would make a middle school coach cringe, he's one of the few players capable of elevating the play of his teammates. He plays with a lot of flair and that's endeared to him to the casual fans.
But the fact of the matter is he sees passing lanes that many other starting point guards can't envision. He's decisive with the basketball, always coupling his dribble drives with a solid plan of attack.
He's still getting a feel for his teammates, yet understands how to put them in the best position to succeed. And some times that means not just spotting an open teammate, but actually leading that player to an open spot.
And he's a pest defensively. Even through an injury-riddled 2012-13 campaign, he's nabbed nearly three steals per 36 minutes.
But that intrigue into what he could become is a far kinder way of saying that we really don't know what he is.
And that uncertainty may cause Minnesota to balk at offering him a max contract, especially for a player who's shot a paltry 36.7 percent from the field over his first two seasons.
Love, on the other hand, has already established himself as one of the premier power forwards in today's game.
He's the best shooting big man the game has going. He converted at least 37 percent of his three-point teams in each of the last two seasons before his shot went awry this year, thanks in no small part to the massive adjustment he faced after returning from a hand fracture.
But Love's bread and butter lies in his ability to clean the glass like a seasoned window washer.
That hand clearly bothered him when he was playing (he's been out of action since fracturing the same hand on Jan. 3 and could miss the remainder of the season, according to Ray Richardson of the St. Paul Pioneer Press). He played fewer minutes this season than he had in the last two. And yet he still corralled an astounding 14.0 rebounds in 34.3 minutes per game.
He's a willing passer (2.3 assists per game), a prolific scorer (26.0 points per game last season) and an extremely intelligent player. He doesn't force shots (44-plus field-goal percentage in each of his first four seasons) despite the obvious talent gap between him and his teammates.
But that's not to suggest that he's a no-brainer for Minnesota, either.
There are legitimate questions about whether Love wants to be with the team. He held no punches in an earlier interview with Adrian Wojnarowski of Yahoo Sports criticizing the franchise's approach to his contract situation in 2012 and questioning the direction of the franchise.
He's repeatedly voiced his desire to play for a contender (via ESPN.com). Is there any chance Minnesota, a team that hasn't been in the playoffs since the 2003-04 season, could possibly field the kind of squad that Love wants over the next 12-plus months?
Ideally the Timberwolves find a way to keep both players in Minnesota. But in an ideal world, Carmelo Anthony is still shredding nets inside the Pepsi Center and Dwight Howard is enjoying the fruits of an annual pass to Disney World.
Should the Timberwolves gamble on a player who's been touted as perhaps the next Pete Maravich or Magic Johnson? Or should they side with the more proven talent, a player who's the ideal mold in today's undersized NBA?
Always a glass half-empty guy, I'm more focused on which of these two players carries a more dangerous worst-case scenario. Is it better to bank a franchise's future on a guy who can't shoot or a potential disgruntled locker room cancer?
Love is a better player now than Rubio may ever become. But he also has the potential to be far more damaging to the franchise should things go awry.
If the Timberwolves gamble big on Rubio and miss, it's just the next bad contract in a league already overflowing with them. But if they miss on Love, they have the potential to be the next hand-cuffed small-market organization.
Next season can't come fast enough for a Minnesota fanbase still reeling from witnessing one of the worst rash of injuries the NBA has seen in some time. Unless the Timberwolves see the progression that pundits tabbed for their star-studded duo this season, that twosome may quickly become a solo act.