Breaking Down The Bucks And Celtics Matchup After Their Summer Of Trades

After a couple very quiet months in the world of NBA transactions, the last week brought a flurry of deals that saw the Milwaukee Bucks and Boston Celtics separate themselves from the rest of the Eastern Conference contenders (on paper, at least).

The sudden arms race began when the Bucks landed Damian Lillard in a three-team deal with the Blazers and Suns, sending Jrue Holiday and Grayson Allen out in the deal. Holiday was then swiftly rerouted this weekend to Boston as the Celtics, who had made the biggest trade of the offseason prior to Lillard by acquiring Kristaps Porzingis for Marcus Smart and others, seemingly recognized they now needed 48 minutes of great guard defense to deal with a Dame-led Bucks team, swooping in to bring the former Buck to Boston for Robert Williams and Malcolm Brogdon (and a couple of picks).

Both teams have gone all-in on this year, and each team is now banking heavily on their starting lineups to carry an immense load by sending out depth to add top-end talent. There are genuine concerns about what happens if either team loses one of their top players, and each are now also banking on health from some stars who have had recent durability concerns.

For Boston, that’s Porzingis, who had a terrific year last year but has already dealt with plantar fasciitis this offseason and, with Williams gone, the Celtics frontcourt grows even thinner. In Milwaukee, it’s Khris Middleton who is vital on the wing, with little behind him now that Allen is gone. And Middleton missed considerable time last year working back from a knee injury that ended his postseason two years ago. Then again, very few teams are capable of winning a championship without a top player and if that is your only goal, as these two have made clear is the case, you might as well create the best possible high-end outcome.

That’s where I want to focus. There’s no way to predict health, and it’s far more fun to imagine what an Eastern Conference Finals showdown could look like between two healthy teams. What makes both teams so fascinating is they are constructed in very different ways, with varying strengths, weaknesses, and matchup advantages that, should we get the seven-game series we’d all love to see, will determine who comes out on top.

We’ll start with the Celtics defense, which has been one of the best in basketball the last two years. Boston now has two of the best perimeter defenders in basketball in Holiday and Derrick White, who they surely hope can mitigate the offensive headaches created by Lillard. Both have long arms and are disruptive on and off the ball, capable of applying ball pressure, navigating screens, and making it increasingly difficult for the Bucks to get into their sets. They also have Jaylen Brown and Jayson Tatum, who are both long, versatile defenders on the wing and they should have a lot of switchability 1 thru 4. Having multiple options to send at Lillard is important, and few teams will be able to keep pressure on Dame for an entire game better than the Celtics.

The question, for this matchup and overall, is in the frontcourt. Like with Lillard, the Celtics will want to show Giannis a lot of different looks, but unlike with Lillard, they don’t have as many good options. Al Horford is still a good defender but is getting older and certainly wouldn’t be the first player you’d select to handle Giannis. Porzingis has rim protection abilities but is not particularly good in space and likewise isn’t the ideal choice to matchup with Antetokounmpo, although he did spend the fourth most time guarding Giannis a year ago while with the Wizards — Giannis scored 19 points in the 14 minutes he was defended by Porzingis, per the admittedly wonky NBA matchup data. A year ago, the four Celtics that spent the most time defending Giannis were Grant Williams (8:24), Jaylen Brown (4:57), Marcus Smart (4:44), and Robert Williams III (3:27). Three of those are now gone, meaning Joe Mazzulla and company will come up with a completely different coverage strategy for facing Giannis, and it will be fascinating to see how they craft that.

For years, the idea against the Bucks was to form a wall and show Giannis as many bodies as possible to deter him from putting his head down and getting to the rim, where he’s almost unstoppable without fouling. With Lillard, that calculus changes considerably as he is the most dynamic perimeter threat Giannis has ever played with by a large margin and is a threat well beyond the three-point line. That requires a very different approach, both when Giannis is on the ball or playing as the screener. What’s interesting is whether the Celtics’ roster seems better equipped to try and limit Lillard and test their partnership by seeing how often Lillard can and will get the ball to Giannis going downhill against a Boston frontcourt that is missing an elite rim protector like Robert Williams was.

One would assume they’ll show a variety of looks to keep them off balance, with some switching when Holiday is on the ball (similar to how they used Smart), showing size with Porzingis, and then asking Brown to shoulder a larger burden as well.

I think how well Lillard and Giannis can get on the same page in Year 1 in their various actions will be the determining factor in how they fare against this Boston defense. There shouldn’t be a singular defensive strategy that can limit them, but the potential pitfalls come in whether they can read and react to varied looks and make the right decision time and again. They clearly have the ability to do that, but building that trust and unspoken bond in pick-and-rolls and dribble handoffs often takes time, even for two elite veteran stars — particularly when they’ve never had someone on their team capable of what each of them can do. That’s part of the excitement for the duo, but it’s also going to take a bit for them to fully understand what it is they can do for each other.

If that process goes smoothly, the Bucks offense is terrifying. Giannis will either have more space than he’s ever seen or Lillard will face less perimeter pressure than he’s ever dealt with, and there isn’t really a good choice on either side of that equation. Khris Middleton will now be firmly the third option and should get better looks and see less attention than he’s gotten in years. Brook Lopez’s ability to set screens and either pop out to the perimeter or roll and seal smaller defenders will make him a quick favorite of Dame’s, and Pat Connaughton will space and cut as the fifth option. It all makes a crazy amount of sense on paper, and we’ll just have to find out exactly how much of a buzzsaw that unit can be on the floor — because given the bench situation, they’re probably going to need to be.

Boston’s offense is dynamic in a similar way now as well, albeit with a bit more frontcourt bias, with Tatum still the engine but Brown now no longer needing to be the secondary ball-handler with Holiday in town. The biggest weakness in Brown’s game has been his handle, but that should be mitigated with Holiday able to start possessions and create for others. Holiday’s big issue in the postseason has been shooting efficiency while shouldering a heavy burden, but in Boston he should be the fourth scoring option, rather than the second or third as he was in Milwaukee (depending on Middleton’s health) and that should accentuate his passing chops while deemphasizing his need to get buckets. Porzingis gives them a frontcourt scoring dynamic they’ve never really had during the Tatum-Brown era, and the pairing of Porzingis and Horford could provide a crazy amount of space for Tatum and Brown to attack the paint because they now are playing alongside two of the league’s best three-point shooting bigs from a year ago.

The challenge for the Bucks on defense is how they can keep Lopez as a rim deterrent while dealing with the spacing abilities of Boston’s frontcourt. For years, Milwaukee has been willing to give up threes in order to shut off access to the rim, but that has made them particularly susceptible to hot shooting series from opponents. For all of the skills of Tatum and Brown, a matchup between the Bucks and Celtics could very well hinge on the three-point shooting of Porzingis and Horford. Both are coming off of career years in that department, and if they can both be 38 percent-plus threats from deep,

I’m not sure what you do to slow down this Boston offense and they can punish Lopez’s deep drop. However, both also posted sub-35 percent shooting seasons two years ago, and if that’s the case then they’ll have a harder time breaking Milwaukee out of their defensive shell.

If they can prove to be threats that need to be accounted for at all times, that also increases the pressure on Lillard as a defender. The idea in Milwaukee is that having Giannis and Brook patrolling the rim mitigate his deficiencies as a defender, with Lopez’s proficiency in drop lessening the impact of Dame’s struggles in screen navigation and the weakside rim protection of Giannis helping to limit the damage of teams drawing Lillard into isolation. However, if Boston’s bigs can draw those two further away from the rim, both as straight floor-spacers and in pick-and-pop, Lillard’s defense will become a bigger story. Boston doesn’t present a great option to hide Lillard anymore, and he’ll likely just have to guard Holiday and White at the point of attack in a series — when Boston goes small with White and Holiday, it’s a lock Lillard will be on White. If that’s the case, Milwaukee is going to have to be great in rotation and communication, which places a lot of stress on the unit as a whole.

The bench units for both teams are major questions, and I’d expect both teams to be looking at possible upgrades as the deadline and buyout market arrive in February. That said, they also don’t have a lot of ammunition to make trades, and buyout players are rarely real impact players so it’s likely they look fairly similar once the playoffs arrive. In Milwaukee, I’d expect a playoff rotation of about eight players (similar to how Denver navigated the playoffs a year ago), with Cameron Payne, Bobby Portis, and Jae Crowder as the frontrunners to make up that rotation — Malik Beasley and MarJon Beauchamp could also crack the rotation in early rounds, but I’d think it gets trimmed pretty tight for the ECF. Crowder and Portis in the frontcourt are solid and provide some small-ball versatility and floor-spacing. While I’m not a huge fan of being reliant on Payne (this was often a concern of mine for Phoenix), if he’s always out there with one of Middleton or Giannis it certainly should help ground him.

Boston has even less experience beyond their top six, with Payton Pritchard, Luke Kornet, and Oshae Brissett (and maybe Sam Hauser?) as the likely options at guard, center, and wing beyond their star-studded six-man rotation. Wing depth is the biggest question for the Celtics behind their star duo, and getting solid contributions from Brissett in spot minutes would be a huge boost for them.

These are two teams that have done what fans always ask their teams to do, which is go all-in on a title window. Both have built unbelievable starting lineups with questionable depth, but when it comes time to sort out real contenders every year, very rarely do we include a team missing a key piece. Both teams have some elite defensive talent that will be put to the test by two offenses that, on paper, can present unanswerable questions. That will put coaching into focus, with two relatively unproven head coaches in Joe Mazzulla entering his second year and Adrian Griffin going into his first. They will have to make the right choices on where to focus their efforts and what to give up on defense, as well as pressing the right buttons on rotations with fairly thin bench units.

All of it makes for fascinating conversation now, but hopefully even more fascinating basketball to watch when they get on the court. Come May, we’ll see if we get the series we all want with both teams healthy, in what could be an all-timer in the East.