Milwaukee Bucks: Free agency contract predictions and primer

Khris Middleton

Middleton is set to sign one of the richest offers of any free agent this summer, and you can fully expect it to cause a combination of consternation and head scratching among certain factions of NBA fans.

The answer to how Middleton positioned himself for such a pay day is not all that complicated, though. Through a combination of great timing on his part, and the challenges facing the Bucks, there’s been something of a perfect storm in terms of the price he’s now able to command.

At this point, Middleton has long been one of the Bucks’ most important players, but it certainly doesn’t hurt to raise your profile with a first All-Star appearance in the season ahead of the most important free agency of your career.

Middleton has all of the leverage in this situation. He’s a player that many teams around the NBA would be all too happy to sign this summer, either as a secondary target for those hunting big fish, or a top target for those looking to make the jump to the next level. He’s an unrestricted free agent, meaning he can speak to any of those teams, and if negotiations with the Bucks were to sour, he could sign with someone else in an instant.

That’s the nightmare situation for Milwaukee. Keeping Middleton isn’t simply about retaining the value Middleton offers as a player, although it is a significant factor which I’ll get back to in a moment. A new deal with the 27-year-old wing ensures Milwaukee remains in meaningful contention at the top of the East, shows their intent to continue chasing a championship, and may ultimately send the kind of positive message needed to convince Antetokounmpo to agree to an extension next summer.

In terms of Middleton’s production, he’s undoubtedly a tier below a player such as Klay Thompson, who he will very soon earn the same amount as, but he remains among the best players at his position and the Bucks wouldn’t have any route to sufficiently replacing him if they were to simply let him walk away.

This isn’t a case of taking the $36 million per year the Bucks could offer Middleton and instead trying to persuade Thompson, Kawhi Leonard, Kevin Durant or Kyrie Irving to play in Milwaukee. The Bucks have just $12 million in cap space, and can only offer Middleton such a deal as he’s their player and they hold his Bird rights.

Also, only the Bucks can offer Middleton a fifth year on a deal this summer, but even that creates an element of risk if the Bucks were to offer him less than the max and tempt him to listen to offers from elsewhere.

The Bucks simply can’t afford to lose Middleton. In a vacuum, his contract is guaranteed to be an overpay, but contracts really shouldn’t be viewed without context. It’s taken a long time for Milwaukee to arrive back to this point in terms of relevance, and they need to make sure they complete a hassle-free negotiation with one of their best players to remain in the NBA’s upper echelon.

Middleton’s last deal was a major underpay just by way of timing, so he’ll likely be eager to get every cent he can this time around. Even if the Bucks aren’t convinced Middleton is the supporting star they need to get over the line in the long-term, retaining him creates the path to future trades centered around an All-Star. Letting him walk, with no real cap space to replace him this summer or in the foreseeable future, and with draft picks owed left, right and center, would seem like the easiest way to guarantee a hard Bucks regression.

Expect this deal to be agreed early.

Prediction: Middleton signs a five-year, $190 million deal to remain with the Bucks