The extension deadline came and went without a deal, so now Monroe will hit restricted free agency this offseason. Detroit can still match any offer in free agency, but it's going to cost them a pretty penny to so, if recent history is any indicator.
Monroe's agent, David Falk, also represents fellow Georgetown alum Roy Hibbert. If you'll recall, Hibbert hit restricted free agency two offseasons ago and signed a max offer sheet with the Portland Trail Blazers that the Indiana Pacers matched.
Monroe and Hibbert are different talents, of course, but players with this combination of size and ability don't come at a discount on the open market. A max deal is almost certainly on the way for Monroe.
Can Detroit afford it? Financially, yes. The Pistons can retain Monroe and stay under the luxury tax, at least for now. But once it comes time to pay Andre Drummond, that could change.
The question is less about money and more about fit at this point. Josh Smith is signed long-term, and his unique skill-set complicates the equation. Can Smith, Monroe and Drummond all co-exist in the same frontcourt? That's the one question that has to be answered this season in Detroit.
Luckily, Pistons general manager Joe Dumars can take his time. A rush to judgment seems unlikely, as it would be prudent for the Pistons to give this a long look to see how viable it is to play all three players together.
Similar to what the Sacramento Kings did with Tyreke Evans this offseason, the Pistons can always work out a sign-and-trade with Monroe's next team if they deem him too expensive or simply a bad fit after this year.
That certainly seems like a more realistic option than dealing Monroe before the trade deadline. That said, if it's very clear that spacing and shooting are issues that will hold Detroit back from making the playoffs, perhaps Dumars would pounce on the right offer.
What would Detroit want in return for Monroe? Most likely, help on the wing would be the top priority.
Brandon Jennings is locked up at point guard, Smith can (and should) play power forward, and Drummond is one of the most promising players in the league at center. While Kentavious Caldwell-Pope and Kyle Singler are promising, that's where the upgrade will likely need to be. After all, the whole point of trading Monroe would be because he's a bad fit with Drummond and Smith, not because he's a bad player.
What teams would be interested in acquiring Monroe in exchange for an enticing wing player? Let's dive in.
The Pelicans have somewhat similar problems to Detroit in that there's a surplus of locked up talent in the backcourt with Jrue Holiday, Eric Gordon and Tyreke Evans, but there's not enough cap flexibility to add a legitimate threat in the frontcourt next to Anthony Davis.
While it's possible that the Pelicans can make it work with this group, exploring alternate options might not be a bad idea.
In this hypothetical deal, New Orleans would send Eric Gordon and Ryan Anderson to Detroit for Greg Monroe, Rodney Stuckey and Charlie Villanueva.
For Detroit, landing a perimeter scorer and underrated pick-and-roll player in Gordon would be a great find, so long as Gordon can stay healthy. While that's a risky proposition, Gordon could provide Detroit with the floor spacing and perimeter defense that's currently missing.
Adding one of the league's best shooting big men in Ryan Anderson to the frontcourt of Smith and Drummond could work as well, as those two players could protect Anderson on the defensive end.
While this move would eliminate Detroit from being a player in free agency for the next few seasons, that might not be a bad thing considering Dumars' tendency to get a little crazy in that setting. Could a core of Jennings-Gordon-Smith-Anderson-Drummond with Singler and Caldwell-Pope off the bench compete in the East? If healthy, I say yes.
For New Orleans, pairing Monroe with Anthony Davis would be a perfect match. For Monroe to be at his best, he needs to be next to a guy who can protect the rim defensively and draw his man out of the paint offensively. Davis supplies that, and at the same time, Monroe could take the bulkier assignments and carve out space in the paint for Davis to thrive.
The big-to-big passing here would be incredible, and building around two twin towers up front would be awfully appealing. The Pelicans would also shed about $8 million in future salary thanks to the expiring deals of Stuckey and Villanueva, which could lead to another big addition in free agency.
Portland Trail Blazers
If Portland's core fails to reach the playoffs once again, perhaps changing up the core would be considered. Because LaMarcus Aldridge is a threat to bolt for free agency after next year, it might be wise for the Blazers to attempt to lock up a franchise big man now.
Monroe would certainly come at a heavy cost, but if for some reason this core isn't good enough to make the playoffs, what's the point of keeping it together?
In this deal, the Portland Trail Blazers would send Nicolas Batum, Joel Freeland and Allen Crabbe to Detroit for Greg Monroe, Kyle Singler and Rodney Stuckey's expiring deal.
For Detroit, adding an incredibly well-rounded young wing like Batum to Smith and Drummond in the frontcourt would be lethal on both ends. Batum isn't a top-option offensively, but he's an accomplished shooter and an improved playmaker that would fit wonderfully.
With Batum, the Pistons could really be a handful in transition and great at protecting the rim with weak-side help.
For Portland, this deal probably only makes sense if Aldridge looks primed to leave. While Aldridge and Monroe could work together offensively really well, there would be defensive issues at play that would be only further complicated by losing Batum.
Trading Aldridge might be an easier option, but if Batum was the ticket to a potential building block like Monroe, it might be hard to pass up.
A smart, passing big man who can gobble up boards and operate out of the high post? Where does Gregg Popovich sign up?
The Spurs could very quietly have plenty of cap room next offseason, particularly if Tim Duncan retires or takes less money in a new deal. Finding a replacement for Duncan is almost impossible, but it's not hard to envision Monroe having success in San Antonio's offense in a similar role.
In this trade, San Antonio would send Danny Green and a second-round pick to Detroit for Greg Monroe.
For Detroit, it might not look like a great haul. Green doesn't provide "name" value, but he's probably the league's best 3 and D player. When you consider Green's top-10 shooting guard status and incredibly cheap contract that runs through next year, it starts to make more sense.
If the goal of trading Monroe is to get better floor spacing and more shooting in the lineup, Green more than accomplishes that.
Would San Antonio trade away Green after his incredible postseason last year, especially given the lack of wing depth on the roster? They might think about it, but pairing Monroe with Leonard and Parker for the future could be a special combination that's too good to pass up.
Detroit should be able to nab one of the last playoff spots in the Eastern Conference, which would probably make a deal during the year for Monroe very unlikely. A sign-and-trade deal would make more sense, barring a great offer coming Detroit's way.
While I do believe there's a strong chance that Monroe will be in a different uniform next year, I wouldn't write off the possibility of Smith, Monroe and Drummond figuring out how to make it work. Smith and Monroe are both wonderful passers, and there are ways to create space through smart design, much in the way the Memphis Grizzlies do.
This will be a year of experimentation for Detroit, but if it doesn't work out, it's pretty easy to identify who the odd man out will likely be.