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The Chicago Bulls had two viable paths this offseason. The first is the one that they actually took. They used their financial flexibility to meaningfully improve their team. So far, that has meant adding Lonzo Ball and Alex Caruso on four-year deals, and in all likelihood, there is more talent to come. 

The opportunity cost of that approach will, in all likelihood, be the other path they could have taken. Zach LaVine is set to be a free agent next offseason. He is also severely underpaid for this season. Despite coming off an All-Star campaign, LaVine will earn only $19.5 million in his contract year. The Bulls could have rectified that by renegotiating his deal up to the max -- roughly $33.7 million. There was a strong case for doing so. LaVine recently said that he wants "respect" in a new deal. With that raise, LaVine would have been a Bull for the foreseeable future. Without it? There's a genuine risk that he bolts as a free agent next offseason. 

So why didn't the Bulls pay him? Because doing so would have cost a significant amount of cap space -- roughly $14.2 million -- that could no longer be used to acquire new players to help the Bulls actually win with him. Realistically, the Bulls were left with a choice: lock up LaVine now, or put a winning team around him in the hopes that doing so convinces him to stay later. They chose the latter. In doing so, barring some unforeseen moves, they have essentially guaranteed that LaVine's salary for next season will remain at $19.5 million. 

You obviously read the headline before you clicked on this story and must be wondering what this has to do with Michael Jordan. Well, had LaVine gotten his raise, his salary could have jumped as high as $33.7 million. That would have been the first time in Chicago Bulls history that any player had ever earned more in a single season than Jordan did in his last dance. Prior to the 1997-98 season, Jordan negotiated a one-year, $33.1 million deal to remain in Chicago. It has been over two decades and still, no subsequent Bull has ever managed to top that figure. Assuming the Bulls don't find a way to bump LaVine's salary, next season will be the 24th in a row that Chicago fails to pay a player as much as it did Jordan.

This might not sound particularly impressive at first glance, but think about how NBA finances work. The salary cap tends to rise fairly steadily. Contracts tend to rise with it, so the highest-paid player in any franchise's history is often whoever that team happens to be paying the most in the current season. 

Here's an example. Entering the 2016 offseason, the highest-paid player in Golden State Warriors history was Baron Davis. During the 2007-08 season, he made more than $16.4 million according to HoopsHype's database. However, the 2016 offseason happened to coincide with the cap spike. That allowed the Warriors to pay Kevin Durant roughly $26.5 million for the 2016-17 season, easily the most the franchise had ever given a single player. But only a year later, they signed Stephen Curry to a new super-max extension. That deal vaulted his salary to just under $34.7 million, breaking Durant's record, but more importantly, it guaranteed him eight percent raises annually. That has allowed Curry to break his own record in each of the three seasons that followed. He will do so again next season by making roughly $45.8 million, and after agreeing to yet another super-max extension, he is going to break his new record at least four more times afterward. In other words, the Warriors will break their franchise record for highest-paid player a staggering 10 seasons in a row.

Yet in over two decades, no Bull has even come close to Jordan's record. The highest cap number any Bull besides Jordan has ever had was the $28.5 million owed to Otto Porter Jr. last season. He was traded at the deadline, though, so if you only count players that finished a season in Chicago, the answer would be Porter in the 2019-20 season in which he earned $27.5 million. So why has Jordan's mark remained intact for so long? That's due to a combination of factors present during both Jordan's career and the league that followed. 

The NBA did not impose a maximum salary on players until the 1999 lockout. Prior to that change, teams were free to pay their players any amount the two sides agreed to so long as it fit within the rules of the CBA. Teams needed cap space to sign free agents from other teams, but their own players had Bird rights. While the concept has become significantly more complex in recent CBAs, the basic concept was the same: they allowed teams to go above the salary cap to retain their own players. Without a maximum salary, a team could pay its own free agent literally any amount of money that the owner could afford. 

Jordan knew this and took advantage of it. When he was a free agent in the summer of 1996, he leveraged the Bulls into a one-year, $30.1 million deal by threatening to sign with the New York Knicks. That deal was so massive that it actually exceeded the salary cap itself, which was set at $24.3 million. A year later, he signed for $33.1 million when the cap was set at $26.9 million. By himself, he managed to earn roughly 123 percent of the cap in that final season. To put that into perspective, the star Lakers trio of LeBron James, Anthony Davis and Russell Westbrook combine to earn roughly $120.75 million. That is still only around 107 percent of the $112.4 million salary cap this season.

As enormous as these deals were, they were inarguably successes for Chicago. The Bulls won championships in both seasons and reaped all of the financial benefits that come with doing so. They were able to rake in the dough from ticket sales, merchandise and every other revenue stream you could think of. Jordan was so remarkably gifted as a player and so obscenely profitable as a business enterprise that signing him to a bad contract would have essentially been impossible. The Bulls would gladly repeat those deals if they could.

But nowadays, they couldn't. The rules regarding max contracts changed the entire equation. The max is tied to one of two things: the cap itself and the player's previous salary. Most players are only allowed to earn a certain percentage of the cap based on how many years they've spent in the NBA, but players can always earn a five percent raise on their previous salary if for whatever reason that figure is higher than their max would otherwise be. That meant that for any player to catch Jordan, they would either need to wait for the cap itself to accommodate them or earn several raises on top of a pre-1999 contract that wasn't subject to the max. No player in the entire NBA topped Jordan until Curry did so during the 2017-18 season. 

Now think about where the Bulls have been ever since then. They haven't made the playoffs since the 2016-17 season, and a big reason for that was their decision to trade Jimmy Butler, the only homegrown player they've developed since a Jordan-caliber salary became possible that might have actually deserved it. Sure enough, Butler's $34.4 million salary for the 2020-21 season actually did top Jordan's … but he earned it as a member of the Miami Heat. Ironically, the Bulls traded Butler in part because of their apparent reluctance to pay him anywhere near that amount. LaVine himself might have had a chance to top it by now were it not for the timing of his last contract. He was not yet a star when he signed a four-year, $78 million offer sheet as a restricted free agent in 2018. That locked him into a sub-Jordan salary. 

If LaVine stays with the Bulls next offseason, he is almost certain to break Jordan's record. The cap is currently projected to rise to around $119 million for the 2022-23 season. That would make LaVine eligible to earn up to $35.7 million -- 30 percent of the cap as an eight-year veteran. If he makes an All-NBA team, he would become eligible for a 35 percent super-max from the Bulls starting at around $41.7 million. Either number would top Jordan. 

If LaVine leaves, things get more complicated. The Bulls would be committed to so many sizable multi-year contracts between Ball, Caruso and Nikola Vucevic that they may not have the space to sign someone new at above Jordan's level. Even if they did, there's no guarantee they'd be able to recruit such a player. It might take several more years at that point for Jordan's record to finally be shattered. For now, that record appears safe for at least another year.

But think about the record that record represents. Unless the NBA's business model drastically changes, it seems almost impossible that any other franchise could go two-and-a-half decades without naming a new highest-paid player. The salary cap simply rises too quickly. Even if Jordan's Bulls record itself falls, his unofficial record for holding that mark the longest appears virtually untouchable. It's a fitting tribute for arguably the greatest player in the history of the sport. His shadow still looms so large over his former team that even after he has gone on to purchase a different one, no Chicago player has ever warranted a salary greater than his, and even when they eventually do, no player in league history will ever approach his financial dominance relative to the rest of the league he was playing in during his career.