MLB isn’t the only league with a gulf between the big-market titans and small-market penny-pinchers. In fact, the superstar-driven NBA might have even more of a parity problem, with headline players consistently forcing their way into the glitzy metropolises, tougher collective bargaining agreement be damned. With Dwight Howard headed to Los Angeles, seven max-contract players (Howard, LeBron James, Chris Bosh, Carmelo Anthony, Amar’e Stoudemire, Deron Williams and Chris Paul, are now congregated in just three cities (Los Angeles, New York and Miami).
As in MLB, the big-market, small-market divergence creates a conundrum for evaluating league executives against each other. Because circumstances are so different between the environments, splitting each into its own category is the most logical method. In this post, I first offer two “prototypes” for all big-market executives to emulate. Then I provide two cases of executives failing to capitalize on their favorable circumstances.
Big-Market Prototypes: Mitch Kupchak (Los Angeles Lakers), Pat Riley (Miami)
As preferred superstar destination spots, cities like L.A. and Miami have no reason to set the bar any lower than championship level. While annual second round playoff appearances may be sufficient for Utah and Indiana, they should not be acceptable for franchises that are theoretically capable of attracting any player in the league.
Likewise, the success of Kupchak and Riley is rooted in a refusal to accept long-term futures that do not include championship contention.
Kupchak and Riley leverage desirable destination cities into superstar talent, swinging for the fences instead of copping out like our friends in the “big-market failures” category. But most importantly, they swing for the fences with discipline, laying off the bad pitches before launching a meatball deep (sorry for all the baseball references—I’ll stop now). The Lakers had drifted in and out of the Dwight Howard rumor mill for a couple of years because Kupchak would not agree to any deal that amounted to much more than a straight-upgrade swap of Andrew Bynum for Howard. It took a while to finally secure those terms, but it was well worth the wait.
Sure, there’s always some luck involved in headline acquisitions—in the Howard sweepstakes, the incompetence of Nets G.M. Billy King and Howard himself allowed the Lakers to become front-runners. Regardless, the final results speak for themselves. As multiple columnists have written (even Bill Plaschke, in a rare quality piece), when the Lakers want a big player, they get him. It’s almost inevitable—the process becoming a mere formality.
At certain points in his front office career, Kupchak seemed to lack the intangibles of his predecessor Jerry West, but since executing the Pau Gasol trade in ’08, Kupchak has firmly established himself as one of the NBA’s best in the blockbuster-deal department.
The same goes for Riley, whose masterful skills of persuasion landed him the Big Three in ’10 and Ray Allen this summer. In the summer of ’04, he landed Shaquille O’Neal from Kupchak (a deal that indirectly led to the acquisitions of Gasol, Nash and Howard. The trade netted the Lakers Caron Butler, Lamar Odom and Brian Grant in return. Butler would be traded to Washington for Kwame Brown, who would later be traded for Gasol. Odom would be dealt to Dallas and his trade exception used to acquire Nash. The Lakers drafted Bynum to replace O’Neal, and he became the key piece in the Howard deal).
After O’Neal and Dwyane Wade led Miami to a title in ’06, Riley waited out four years of irrelevance until making his next league-bending splash.
Riley and Kupchak dream big and deliver, with impeccable patience possibly being their most valuable asset of all. For our big-market failure executives, patience is a trait you certainly will not see.
Big-Market Failures: Billy King (Brooklyn), Glen Grunwald/James Dolan (New York)

While Ian O’Connor (or whoever wrote his headline) deemed Billy King the “King of Brooklyn” last month, I was not quite so complimentary. Indeed, King convinced Deron Williams to turn down Dallas and stay with the Nets, preventing less-than-ideal circumstances for the team’s Brooklyn move from entering disaster mode. King also allowed the situation to become so desperate that the antidote was a trade for the talented but absurdly overpaid Joe Johnson.
Taking note of the crap sandwich Orlando received in return for Howard, King looks worse than ever. At the 2012 trade deadline, the embattled G.M. dealt his first round pick to Portland for Gerald Wallace.
The pick ended up being No. 6 overall.
The Magic front office is certainly delusional, but would they really have been delusional enough to reject an offer of Brook Lopez, MarShon Brooks, the No. 6 pick and future first-rounders? Lopez is better than any player Orlando received in the Howard four-teamer (despite being the most anemic 7-foot rebounder since the legendary Wang Zhi-Zhi), Brooks is cost-friendlier than Afflalo and only a step below him skill-wise, and whichever player the Nets drafted No. 6 would likely turn out better than Afflalo, et. all, as well. Shipping out expiring contracts for Johnson also eliminated King’s ability to sweeten a Howard offer with the ability to take back some of the Magic’s burdensome long-term salary.
Unfortunately, King lacks (severe understatement) the Kupchak/Riley magic touch, the facility to convince his superstar that championship-level talent will arrive on his watch (and actually make it arrive). Kupchak had to earn such trust from Kobe after the debacle of the mid-2000s, but he has erased all memory of that mini-era with pure mastery in the last four-plus years (Kupchak’s only flaw is an affinity for using the mid-level exception to overcompensate the white men bench club of Vladimir Radmanovic, Luke Walton, Sasha Vujacic, Steve Blake and Josh McRoberts).
King, as I argued before, had proven so little to Williams than even a move to the mega-market of New York (which enticed him to play for the Nets in the first place) could not sway his decision as much as the acquisition of Johnson, a.k.a. Rashard Lewis 2.0 (wait 2-3 years and see how accurate this comparison becomes). When Dwyane Wade re-upped with Miami in ’10 before either Chris Bosh or LeBron James signed, he trusted Pat Riley could do his job. Williams could not trust King to do his.
Thus, instead of a championship contender built around the power duo of D-Will and Dwight, King has assembled Williams and four overpaid whipping boys (Johnson, Wallace, Lopez, Kris Humphries) for the Heat in the Eastern Conference (semi)finals. When a big-market team that could theoretically attract any superstar caps out its potential for the next 3-4 years, you know a dud G.M. is running the show.
Speaking of capping out your potential, Brooklyn’s new cross-town rival, the New York Knicks, chose the same path of future playoff ignominy by failing to match the Houston Rockets’ back-loaded, three-year offer to Jeremy Lin.
Since it’s possible that owner James Dolan’s spite is entirely responsible for the Lin decision, I listed him alongside G.M. Glen Grunwald as a “big market failure.” Dolan has a well-documented history of screwing things up, but this might be his lowest moment yet. For the first time in years, the Knicks had a legitimate championship core of superstar player (Carmelo Anthony), defensive anchor (Tyson Chandler) and dynamic scoring/distributing point guard (Lin). Certainly it was no Heat or Thunder core, but with a no-nonsense coach in Mike Woodson, the Knicks finally seemed like a team on the rise.
Notice the exclusion of Amar’e Stoudemire on the above list, and keep in mind that the Knicks’ stunning shortsightedness with how to handle Stoudemire ultimately allowed them to financially justify their Lin decision.
The issue at hand with the Lin contract was its approximately $15 million third year, which would saddle New York with four mega-contracts in the more punitive upcoming luxury tax era. While concluding that they could only pay three of those contracts, the Knicks apparently forgot that they need a potentially elite point guard like Lin far more than they need Stoudemire.
The incompatibility of Stoudemire and Anthony has already been hashed out ad nauseum—they are two ball-dominating scorers who don’t defend or pass. And as nine and eight year veterans, respectively, they don’t seem particularly intent on ever adjusting their styles to suit each other.
So why ’Melo over Amar’e? Simply put, he’s better. Although Anthony has always teetered just outside the NBA’s top 10 players, he has the ability to reach the superstar pinnacle of contemporaries like LeBron James and Dwyane Wade.
The 2004 Pistons remain the only NBA team in over three decades to win a championship without a top-10 player on their squad, and the did so by with one of the best defenses of all time. The Knicks are no defensive juggernaut, so regardless of Anthony’s shortcomings in the realm of over-isolation and unwillingness to improve weaknesses, they need a player of his caliber to have any chance at the title. An all-around point guard and Defensive Player of the Year at center are two more extremely valuable pieces.
What the Knicks don’t need is Stoudemire. Amar’e might be even less valuable to New York than Steve Novak, who provides similar defensive ineptitude but spreads the floor with three-point shooting and doesn’t take the ball away from Anthony.
I’m not saying Stoudemire is a useless player, period. He’s still anywhere from top 25-50 in the league, but he has no role in New York. After signing Lin, the Knicks could have dangled Stoudemire for role players/expiring contracts. I used the ESPN Trade Machine to compile a list of possible trades:
Trade #1: Stoudemire to Milwaukee
- New York receives: Ersan Ilyasova (sign-and-trade), Luc Richard Mbah a Moute, Mike Dunleavy (expiring contract)
- Milwaukee receives: Stoudemire
Trade #2: Stoudemire to Toronto
- New York receives: Andrea Bargnani, Tayshaun Prince, Austin Daye (expiring)
- Toronto receives: Stoudemire
- Detroit receives: Jose Calderon (expiring)
Trade #3: Stoudemire to Golden State
- New York receives: David Lee, Andris Biedrins/Richard Jefferson (expiring in ’14)
- Golden State receives: Stoudemire
Trade #4: Stoudemire to San Antonio
- New York receives: Channing Frye, Jared Dudley, Tiago Splitter (expiring), Derrick Byars (expiring)
- San Antonio receives: Stoudemire
- Phoenix receives: Stephen Jackson (expiring), Cory Joseph
Thanks to a hefty contract and declining skills, STAT wouldn’t yield the Knicks a spectacular haul, but anything they received would have put them in better shape if it meant keeping Lin. And players like Ilyasova, Lee, Bargnani and Frye could have fit nicely as third offensive options behind Anthony and Lin.
While common consensus holds that the Lin poison pill doomed New York, I believe that the structure of the deal actually favored the Knicks. Lin would be paid below-market value for two full years, giving New York ample time to pursue a Stoudemire trade before suffering severe luxury tax consequences. Even in the worst case scenario of a complete Lin tanking, he would have a short-term deal with a sizable expiring contract to dangle for another impact player.
Alas, Houston G.M. Daryl Morey knew that the New York front office would enter panic-mode too quickly to consider any other options. Morey played his hand perfectly, adding a new episode to the fascinating front office career of this tortured genius (more on that in an upcoming post).
Whether it was Grunwald, Dolan or both calling the shots, the Knicks just closed their championship window. At least New York and Brooklyn should be able to enjoy an exciting Subway Series rivalry among 50-win teams. LeBron and the Heat will eagerly devour the second-round leftovers.

The new reality of the Knicks dooms Anthony to eternal sub-James-and-Wade status, which is unfortunate for ’Melo. But the Knicks’ star himself deserves some of the blame. Anthony forced a trade to New York seeking a “family” environment, and he was allegedly lukewarm about Lin for taking his seat at the head of the table.
If a family environment is the goal for Anthony, he chose a dysfunctional one in New York—Patriarch Jimmy D, a coach with whom he clashed (Mike D’Antoni) and a co-star, who, despite being a veteran in experience, is an immature rookie in practice. Stoudemire has spent his last few months punching a fire extinguisher, dishing out a homophobic epithet on Twitter and presumably continuing to avoid making adjustments to his game.
Anthony has always felt unfairly relegated to second fiddle behind his buddies James and Wade, who both have rings that ’Melo doesn’t (even Bosh has surpassed him in the jewelry department). He’s always felt that the criticisms of him as a selfish player are unfair, and that he simply needed the right situation to flourish. However, in his mission to create that type of atmosphere in New York, he unwittingly played right into the selfishness/lack-of-leadership narrative that has dragged down his whole career.
Even if the Knicks retained Lin, Anthony had already stated publicly his opinion of the point guard’s “ridiculous contract.” That doesn’t sound like much of a team unity builder. J.R. Smith also commented that Lin’s salary could spurn friction in the Knicks’ locker room, and it very well could have, considering the plainly obvious leadership vacuum there.
If Lin stayed a Knick with his $25 million salary, Anthony would have done nothing to prevent team chemistry from turning toxic. ’Melo might be satisfied that Lin is gone and that he can be the sole headliner, but little does he know that his best opportunity at pulling even with his ’03 draft-mates just passed.
Despite Anthony’s role in the Knicks’ collective failure, it still circles back to the front office, which chose Anthony as its building block in the first place. Instead of honing in on CP3 and/or Howard, Dolan overrode the desires of former G.M. Donnie Walsh and brought the ‘Melodrama to Broadway. Meanwhile, guess who didn’t bite on Anthony? The Lakers, who kept Bynum until they could parlay him into Howard.
Patience truly is a virtue.
Next up: Small-Market Prototypes and Failures