Bucks get: Guard George Hill, forward Jason Smith and a 2021 second-round pick
Cavaliers get: Guard Matthew Dellavedova, center John Henson, a 2021 first-round pick, a 2021 second-round pick and a 2022 second-round pick
Wizards get: Forward Sam Dekker
Get more trade grades for every deadline deal here
Milwaukee Bucks: A
For the Bucks, this is probably two parts a long-term salary move and one part a basketball move for this season. Dellavedova and Henson were set to make a combined $20.1 million in 2019-20, the final season of their contracts, when Dekker will be a restricted free agent (if Milwaukee chooses to make him a qualifying offer) and Hill's $18 million salary is just $1 million guaranteed through July 1. That gives the Bucks more flexibility going into what figures to be a fascinating offseason for one of this season's pleasant surprises.
Of Milwaukee's five starters, just one -- MVP contender Giannis Antetokounmpo -- will assuredly be under contract on July 1. Shooting guard Malcolm Brogdon will be a restricted free agent, point guard Eric Bledsoe and center Brook Lopez will be unrestricted and small forward Khris Middleton has a $13 million player option he's all but certain to decline.
As a result of that uncertainty, there are a couple of reasons the Bucks would value more cap flexibility next summer. If either Bledsoe or Middleton decides to leave, shedding the salary of Dellavedova and Henson would give Milwaukee somewhere in the neighborhood of $20 million to pursue a replacement. (The exact number will depend not only on where the salary cap is set and which player it is, but also whether the Bucks receive an expected long-term injury exclusion to remove Mirza Teletovic's $3.5 million in stretched salary from their cap sheet.)
Alternatively, in the happy case that Milwaukee can bring everyone back, the luxury tax would become a concern. While Bledsoe might not sign for much more than his $22.5 million cap hold, Middleton stands to receive a much larger pay increase over his current $13 million salary. Given the number of teams that plan to have max cap space next summer, it wouldn't be surprising to see Middleton get an offer starting at his estimated $32.7 million maximum. Playing out those two scenarios would leave the Bucks with approximately $13.5 million to re-sign Brogdon and Lopez while avoiding the tax, assuming the injury exclusion for Teletovic.
Under almost any scenario, then, saving money next offseason will be beneficial for Milwaukee. And while that cost a future first-round pick, the Bucks were also able to modestly upgrade for this season as they contend in the Eastern Conference.
Wrist surgery last month was likely to keep Henson out for several months. Meanwhile, Dellavedova had largely fallen out of Mike Budenholzer's rotation, playing just 97 minutes this season. While Milwaukee has gotten solid play off the bench from guards Pat Connaughton and Donte DiVincenzo, another perimeter reserve would be helpful. The Bucks had been outscored by 3.6 points per 100 possessions in Dellavedova's limited action, per NBA Advanced Stats, and have a minus-2.9 net rating in second-year wing Sterling Brown's 148 minutes.
Undoubtedly, Hill will be an improvement on the players at the fringes of Milwaukee's rotation. Though no longer the playmaker and shot creator he was in his heyday with the Indiana Pacers and Utah Jazz, Hill remains a capable catch-and-shoot threat (46 percent on 3s so far this season, and better than 40 percent each of the last four) with the ability to run an offense.
How large a role Hill can carve out with the Bucks will depend on whether his poor defense this season in Cleveland was a product of disinterest on a rebuilding team or physical decline that can be traced to Hill's age (32) and the lingering effects of a toe injury he dealt with in Utah. It's less likely Smith can help, and the possibility that he takes minutes away from better center options causes me to downgrade this deal slightly from the version reported originally that included Dekker.
Getting Hill alone wouldn't be worth a first-round pick at this point. After all, the Cavaliers gave up only a 2020 second-round pick and cash (along with Iman Shumpert) to get Hill from the Sacramento Kings at last season's trade deadline. However, when the cap relief Milwaukee achieved in this deal is considered, as well as the protections on the pick (at lightest top-eight protected in 2024 before converting to two second-round picks if not conveyed by then, per ESPN's Zach Lowe), it's a solid move at worst with the potential to be a huge win.
Cleveland Cavaliers: B
The Cavaliers' sell-off, which began last week when Kyle Korver was dealt to Utah, continues with Hill's departure. Though Hill was starting for Cleveland alongside rookie point guard Collin Sexton after returning from a shoulder sprain, he was not part of the Cavaliers' future plans and a trade seemed inevitable.
From Cleveland's perspective, taking on long-term salaries using the lightly guaranteed contracts of the team's veterans in exchange for draft picks is a good strategy. The Cavaliers are too early in their rebuilding process to make use of cap space in free agency, and they can use additional draft picks to fortify a stock depleted by the pursuit of championships with LeBron James on the roster.
The first-round pick Cleveland got from the Bucks almost certainly won't arrive in Northeast Ohio until 2022. Because Milwaukee already owed a first-rounder to the Phoenix Suns from the Bledsoe trade, this pick won't convey until two years after that happens due to the so-called Stepien Rule named after the former Cavaliers owner who traded multiple future first-round picks.
The Bucks' 2019 first-round pick goes to Phoenix only if it lands between No. 4 and No. 16, something projections based on ESPN's Basketball Power Index give zero chance of happening this season. Much more likely, Milwaukee will lose its 2020 pick (top-seven protected) to the Suns, meaning 2022 would be the earliest the Bucks could send this pick to Cleveland.
As ESPN's Adrian Wojnarowski noted, getting the deal done Friday allows both teams to potentially aggregate players acquired in the trade on deadline day. That seems more likely to benefit the Cavaliers, who could seek to take on even longer contracts in pursuit of additional draft picks. Flipping Henson, particularly if he's near a return from surgery, would make sense given he's still a rotation-caliber player and Cleveland is flush at center with Larry Nance Jr., Tristan Thompson and Ante Zizic.
Washington Wizards: B-minus
The $5.45 million player option the Wizards handed Smith for this season, the third of his contract, was one of a number of costly mistakes by team president Ernie Grunfeld that have left Washington in the luxury tax. This deal slightly mitigates that bill, and gives them a player with a better chance of contributing this season.
In a complex move affecting protections on a pick already owed to Milwaukee from this year's Jodie Meeks deal, the Wizards effectively traded the Bucks either their 2020 or 2022 second-round pick. Previously, Milwaukee got Washington's 2020 second-round pick if it fell in the top 45 picks, or otherwise the 2022 second-rounder. Now the Bucks will get both, per Fred Katz of The Athletic DC, leaving the Wizards without a second-round pick in any of the next four drafts.
By swapping Smith for the cheaper Dekker, Washington saves more than $5 million in salary and luxury tax. If the Wizards want to further cut into their tax bill, Dekker should be much easier to move to a team with a trade exception without draft compensation than Smith would have been.
Because Washington was able to use the trade exception generated by the Meeks deal to take back Dekker, the Wizards also generated a larger exception for the value of Smith's salary -- though naturally, it's unlikely they would use that to add talent this season as taxpayers.