Dan Gilbert is a tremendously wealthy man.
Depending on who you ask, Gilbert's net worth is anywhere from $24 to $29 billion, give or take a few hundred million. As the head of the nation's largest mortgage lender, now known as Quicken Loans, Gilbert has amassed a large fortune that continues to grow.
One of his investments that also continues to grow is the Cleveland Cavaliers. Gilbert bought the team in 2005 for a then-record-price of $375 million. 20 years later, Forbes estimated the franchise's value at $3.95 billion. That's an incredible return on investment. During Gilbert's time owning the team, while he has certainly had some rocky moments, the Cavs have made it to five NBA Finals and won the championship in 2016.
Gilbert is a businessman, and as such he likely tries to come out of every business transaction having made money. Yet he also likely understands the value of on-court success and what it does for a team's overall profit line. That makes it difficult to parse exactly where the team's priorities lie heading into the NBA Trade Deadline.
The Cleveland Cavaliers have multiple Trade Deadline options
With the NBA Trade Deadline just one week away, the paths ahead of the Cleveland Cavaliers tend to fall into three categories. The first is that they simply stand pat, keeping together the roster that is leading the Eastern Conference and letting this season play out.
The second is pushing in their remaining assets -- namely, some combination of their 2031 first-round pick, rookie Jaylon Tyson and potentially a 2030 pick swap -- to get an upgrade, be that a shooter like Cameron Johnson or a defensive wing.
The final path seems unexpected given the Cavaliers' status as a title contender, but it's also one that many around the league expect Cleveland to take: saving money.
Specifically, the Cavaliers are $1.9 million above the luxury tax line for this season. Historically, teams that are that close to the line tend to do what it takes to get "out of the tax" -- it not only saves them from paying an extra tax on that $1.9 million, it means they become eligible for the luxury tax payout to non-tax teams, which could be upwards of $20 million this season.
On top of that money for this season, however, getting out of the luxury tax would reset the clock on the dreaded "repeater tax" which kicks in for teams in the tax multiple years in a row. Because Donovan Mitchell and Evan Mobley will be starting new contracts next season that pay them significantly more money, the Cavaliers are likely going to be in the luxury tax for the next few seasons. If they remain in the tax this year, those future teams will be much more expensive.
That's why everyone analyzing the Cavaliers ahead of the Trade Deadline seems to be convinced that they will take "path No. 3" and focus on shedding salary. When ESPN's Bobby Marks broke the entire league into trade tiers, he put the Cavaliers into "Watching the bottom line" with other teams looking to shed salary.
It's not simply Marks who expects a cost-cutting approach to the deadline: literally everyone seems to think so. Michael Scotto of HoopsHype reported that while the Cavaliers have stated that could pay the luxury tax, that "NBA executives elsewhere are skeptical" and that they think Cleveland will "try to duck the tax with a trade." Dan Favale of Bleacher Report saw the report that Cleveland is willing to pay the tax and said "that feels like a lie" when discussing trade candidates for the Cavs this year.
So now we circle back to Dan Gilbert's net worth. Engaging the repeater tax is an extremely punitive reality, especially for teams tens of millions into the tax. It will cost Gilbert a lot of money to keep the team intact for the next four, five, six seasons if he is forced to pay it.
Yet at the same time, the repeater tax doesn't come with any team-building restrictions other than paying more money. If Gilbert is comfortable footing a higher bill -- as Joe Lacob and Steve Ballmer have done in recent seasons -- then he will steer the Cavaliers to make moves solely to maximize their on-court play. If he wants to "win the transaction" then the savvy business move is probably to move off of something now to save a lot of money down the road.
Is Dan Gilbert willing to pay up? Is the Cleveland front office "lying" and they are actually going to shed money? One week to go to find out this team's priorities at the Trade Deadline, a deadline that could have shockwaves that extend for years to come.