With the exception of "sure thing, can't miss" max players, negotiating a contract extension can be awfully tricky for both parties.
Players don't want to undersell themselves unnecessarily and miss out on a big payday in restricted free agency, but they also want long-term security.
In that same vein, franchises dread overpaying for players. Locking a player up before a breakout season (see: Steph Curry, Golden State Warriors) is the ideal scenario for a team, but even then there are still risks involved.
As we've seen so far this offseason, small-market teams have been more willing to extend their franchise cornerstones nice and early. The Milwaukee Bucks kicked things off with an extension for Larry Sanders, and the Washington Wizards, Indiana Pacers and Sacramento Kings followed up with max contracts for John Wall, Paul George and DeMarcus Cousins.
For those teams, the reward of establishing a good relationship and removing any potential distractions this season outweighed the risks.
With the October 31 extension deadline approaching, will we see teams with other big names from the 2010 draft class follow suit?
Detroit Pistons: Greg Monroe
The Detroit Pistons have leverage in their discussions with Greg Monroe, and it comes in the form of Andre Drummond. After a tantalizing rookie year from Drummond and the signing of Josh Smith in free agency, Pistons GM Joe Dumars may be able to play a little hardball.
Monroe would almost certainly receive a max contract in restricted free agency, but it's not guaranteed. That uncertainty might allow the Pistons to shave a few million off Monroe's deal, but not much.
Either way, it's hard to imagine the Pistons planning for the future without Monroe. The most likely scenarios are either a trade, an extension or a matched offer in free agency. Losing Monroe for nothing can't possibly be an option given Detroit's lack of appeal as a free-agent destination, and Dumars and company know what to expect when a young big man hits the market.
While Monroe's representation will undoubtedly point to the money DeMarcus Cousins received and try to prove that as the going rate for Monroe, the Pistons might be able to bluff their way to a slightly lower price.
Extension Comparison: Pointing to Al Horford's, five-year, $60 million dollar contract extension from 2010 might be a reasonable comparison for Dumars to make. Monroe's statistical production has been very similar to Horford's first three seasons, and the questions of whether Monroe is a center or power forward are similar to the questions Horford faced as well.
If the two sides can meet in the middle between $12 million and $15 million a year, this could probably get done. It seems more likely, however, that the Pistons let the year play out. It still needs to be seen whether Monroe can mesh with Drummond and Smith, and it's possible that Drummond becomes so good that he demands a full starter's slate of minutes. Leaving the trade window open for a full season makes sense as well.
Prediction: No extension. Detroit will play the trading field, then match in free agency. If an extension does happen, five years, $67.5 million.
Utah Jazz: Derrick Favors
Finally, Derrick Favors won't be buried on the Utah Jazz bench behind Al Jefferson and Paul Millsap any longer. While that's a good thing for Favors in what amounts to a contract year, it could cost the Utah Jazz a pretty penny if they're unable to lock up the promising young big man before October 31.
Favors played a career-high 23 minutes a night last season, and for three seasons we've only been offered glimpses of his immense potential. Favors is mobile and can defend pick-and-rolls extremely well, but his size also lends well to protecting the rim. He's putting it together offensively, but he's shown the touch and the moves to be a force on that end as well. And he's just 22-years-old.
What's potential without substantial production worth? That's the question for the Jazz. Buying low on Favors and banking on his potential might be the best decision, because players with his talents won't come at a discount once they hit the open market.
For that reason, Favors may want to bet on himself this season. He'll finally have the minutes and the touches to put up big numbers this season, which is the only thing stopping him from a max deal.
Extension Comparison: A deal similar to Serge Ibaka's four-year, $49 million dollar extension from 2012 might be a good starting place. Although Ibaka's deal included a "contender" discount that Utah's won't, the shortened length of the deal might be appealing to Favors, who could line himself up for a max deal down the line a little quicker. Larry Sanders also reinforced a similar value for defensive specialists by signing a four-year, $44 million dollar deal.
Ibaka makes for a pretty good statistical comparison for Favors, primarily because of the defensive focus and limited minutes both players shared in their first three seasons. Favors isn't the shot-blocker Ibaka is, but it's not a stretch to say he could be the better overall defender in the near future.
Prediction: No extension. Favors will bet on himself this year and wait for restricted free agency. If an extension does happen, four years, $48 million.
Philadelphia 76ers: Evan Turner
While he's been a disappointment thus far, Evan Turner did show some signs of life last season. With very little competition for shots since Jrue Holiday is now in New Orleans, Turner has a chance to put up some big raw numbers for a really bad 76ers team this season. Points are often put on a pedestal in free agency, so this could be a year where Turner bumps up his value.
That said, Turner's future probably doesn't exist with the Philadelphia 76ers. Teams entrenched in the beginning stages of a rebuild rarely commit large chunks of salary to players who, at best, make the team mediocre. And from Turner's side, extending at a cheap enough price to make the 76ers bite would be selling himself short before he has the chance at a breakout season.
For those reasons, it doesn't make sense for either side to negotiate an extension.
Extension Comparison: The situations are different, but you could easily see Turner following a path of another disappointing top-three pick in O.J. Mayo. After the Memphis Grizzlies passed up on extending Mayo, they also declined to make a qualifying offer, which made Mayo an unrestricted free agent.
Similar to Mayo, Turner has talent and should get a decent contract down the line, but it will almost certainly be with a different team than the one who drafted him.
Prediction: No extension. Philadelphia will look to trade. If an extension does happen, four years, $26 million.
Utah Jazz: Gordon Hayward
The Utah Jazz might be playing with fire if they let Derrick Favors and Gordon Hayward both hit the market as restricted free agents. Favors might be tougher to keep because of his potential and position, but the Jazz could find value in keeping Hayward, a player who oddly hasn't seen his reputation catch up with his high level of play.
Hayward's minutes have been limited much like Favor's (come on, Tyrone Corbin), but he's shown all the abilities of a complete offensive player. Guys with Hayward's size and skills on the wing don't come around all that often, and like Favors, Hayward should get a bigger chance to put that on display this season.
Extension Comparison: It's a little scary how similar Hayward is to Danilo Gallinari. Both players can shoot from deep and use their great size to draw lots of fouls at the rim, and over their first three seasons, the two small forwards posted a nearly identical PER.
Gallinari signed a four-year, $42 million dollar extension in 2012, and that seems like a price point both Utah and Hayward should be willing to accept.
Prediction: Hayward signs a four-year, $42 million dollar extension.
Phoenix Suns: Eric Bledsoe
No one's free-agency value hinges more on their performance this season than Eric Bledsoe's. If Bledsoe struggles next to Goran Dragic playing off the ball, his value could take a dive, as very few teams need a starting point guard. If Bledsoe works well with Dragic and is a major factor no matter what position he's at, though, his value in free agency could skyrocket.
It would make sense for the Suns to see what they have with Bledsoe and Dragic together before investing long term, but this might be the last chance to get a player of Bledsoe's ability at a steep discount.
At the same time, Bledsoe could instead decide to bet on himself in free agency and at least attempt to pull down one of the few starting point guard spots available.
Ultimately, there's probably too much unknown on both sides for a committal at this juncture.
Extension Comparison: There really aren't many players in the league quite like Bledsoe, but Tyreke Evans might be a good example for what Bledsoe's deal in free agency could look like as an athletic stud without a true position.
Prediction: No extension. Both sides will wait to see how it plays out. If an extension does happen, four years, $36 million.