Carmelo Anthony used to have time to let dollar signs cloud his vision.
While still playing out his rookie contract in 2006, the Denver Nuggets offered him a five-year extension that would net him the highest annual salary possible at the time.
While LeBron James, Dwyane Wade and Chris Bosh—Anthony's 2003 draft-class brethren—all settled for lesser guaranteed deals with shorter commitments, they opted for a more lucrative option long term: the ability to hit the open market simultaneously and join forces in 2010.
Ignoring the type of free-agency synergy that eventually paid off in hardware for the Miami Heat trio, Anthony took the maximum deal. And though it may not have been the better basketball decision, 'Melo was fine, still. He was only 22, with the prime of his career still far in the distance.
Five years later, Anthony faced another dilemma. With an NBA lockout looming after the 2010-11 season, the All-Star forward was ready for a change of scenery as his deal was set to expire, but he fretted the risk of losing millions by signing a fresh free-agent deal under a new collective bargaining agreement.
With the New York Knicks interested, and Anthony desperate for a powerful market, there was a match. But there was also a decision to be made: 'Melo could've simply waited it out, signed with the Knicks outright post-lockout, for a slightly lesser total than he could've racked up in pre-lockout.
Instead, he again secured the financial gain and forced a trade to the Knicks while the old CBA still stood, though it cost his new team four players and three draft picks.
Still, 'Melo was fine. He was just 26, under contract for three more years and paired with an All-Star teammate in Amar'e Stoudemire. Anthony knew they were in for a small rebuild after the deal, but the full length of a new contract seemed like sufficient time for management to build a winner.
His three years are up, and though his checking account would disagree, opting for the max has now failed Anthony twice.
He never gave himself the chance to chase 'chips with LeBron. Partnering with Chris Paul in New York could've been the vindication he needed, but 'Melo's arrival had the Knicks tapped out of trade chips before they could even make the call.
After earning more than $135 million through these maneuvers, it's tough to contest his logic.
This July, it'll be time to lock in another deal. He'll be hitting the open market for the first time ever. But also for the first time ever—as he reaches the age of 30 this month, still with no meaningful success to his name—signing on the dotted line won't be a mindless mathematical calculation.
For the first time, should he value Benjamin Franklin over Larry O'Brien, 'Melo won't be fine.
After New York's turmoil overshadowed its success during Anthony's three-plus seasons there, he'll finally be forced to consider every option. Chances are, for the player who's never left a dime on the table in negotiations, money won't even be a factor at all.
He practically said as much when he stated publicly that he is open to re-upping with the Knicks on a discounted deal if it meant a better chance at a title. While in New Orleans that Friday during All-Star Weekend last February, Anthony addressed the proposition (via ESPNNewYork.com's Ian Begley):
Without a doubt. Any opportunity I have to build that up in New York, I'd do it. I told people all the time, always say, "If it takes me taking a pay cut, I'll be the first one on [Knicks owner] Mr. [James] Dolan's steps saying take my money and let's build something strong over here."
Taking a pay cut with the Knicks, depending on the size, would essentially eliminate the advantage New York has in possessing Anthony's Bird rights. They can offer him up to $129 million over five seasons, while other suitors max out at four years and $96 million.
It would only behoove the Knicks to bring 'Melo back on a discounted deal, as a full max would leave them in a severely hamstrung spending situation moving forward. This essentially renders New York's Bird rights-possession irrelevant, and put the Knicks on a level playing field—in regard to spending on Anthony—as every other suitor.
But, as Anthony has implied, the total amount won't be the deal-breaker.
What he will be concerned with is measured success on the court. And, as we stand in 2014, the Knicks can't offer him that.
With Stoudemire and Andrea Bargnani set to make about $35 million combined next season, New York will be capped out with or without Anthony. Barring a Phil Jackson "Zen miracle," next year's roster will largely resemble the one put together this past season—the one that went 37-45, despite one of Anthony's best years to date.
If Anthony invests the rest of his prime in the Knicks, it won't be a matter of cash nor will it be banking on 2014 win totals. Should he please the Big Apple and re-sign, it will be solely because of the franchise's direction that Jackson has laid out to him. 'Melo must trust that the organization's vision is markedly different under Jackson and that the team can turn its fortune around in short order.
Closing in on the final prime years of his career, Anthony will need significant help leading a team to the promised land.
Anthony will be banking on Jackson acquiring a bona fide talent in 2015, when the team will finally have room to spend. But it's worth noting that teams of that nature—that strip nearly an entire roster and reappear the following season with a star-studded lineup—rarely reach championship heights in just one season. Even the Heat failed to bring home a ring in 2010-11.
Using this logic, the earliest the Knicks would be able to compete for a championship would be the 2016-17 season, which would be Anthony's 13th in the league.
Over the last three seasons, according to Basketball-Reference.com, Anthony put up .172 win shares per 48 minutes (league average is roughly .100). Also according to the site, over the last five years, just four different forwards have enjoyed success like that past their 13th NBA campaign. Only one occurrence has resulted in a title.
|Since 2009-10: SF/PFs in 13th Season or Later to Post .173 WS/48|
|NBA Championship season|
Judging by these examples, it's hard to expect 'Melo to keep up this level of play by the time New York plans on chasing titles. By that time, a 32-year-old Anthony would need a roster packed with good defenders, excellent shooters and certainly a younger star to help shoulder the load.
If he returns, it means he fully trusts that Jackson will assemble a team of this makeup.
It's also hard to expect 'Melo to buy into a plan that requires him to wait until he's 32 to make a serious run, when he can fit right into the Houston Rockets' or Chicago Bulls' championship hunt right now.
But if you find him in Madison Square Garden next season wearing orange and blue, trust that it'll have little to do with a dollar sign. Anthony understands the only way to compete as a Knick is to diminish his own salary and watch New York's 2015 cap room balloon.
And he'd only agree to such a sacrifice if he's completely sold on Jackson's pitch: that he can pilot a 'Melo-led Knicks team to glory—and quickly.
More than three years after their marriage began, Carmelo and the Knicks are both vastly different than before. This Knicks management isn't one that will drown Anthony in James Dolan's dollar bills nor is Anthony a player who would be interested in such a deal with the devil.
Both sides have a clearer view of the future now than they did the last time they sat across the negotiating table. Both sides are tired of failure, and both will be in positions to right their wrongs in the near future. For New York, it's simply a matter of that future being as near as Anthony prefers.
For the first time, Anthony can no longer afford to misplace his trust. And after a decade of lucrative disappointments, it appears that a wiser 'Melo has changed his ways.
To retain him, the Knicks will have to convince their star that they've changed, too.
Follow me on Twitter at @JSDorn6.
Stats gathered from Basketball-Reference.com.