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All Things Considered: Grading the Bucks’ Offseason Moves

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In just one week, Milwaukee has overhauled their roster. How did they do?

New Orleans Pelicans v Milwaukee Bucks Photo by Jesse D. Garrabrant/NBAE via Getty Images

In a normal year, we would have plenty of time to digest the litany of transactions that define the NBA offseason. With the NBA Draft in June and free agency opening in July, we usually would have months to process and ponder the machinations of the league’s annual roster restructuring.

This is not a normal year. Nevertheless, the Milwaukee Bucks have substantially reinvented their roster, in some ways that we expected and others that came as a surprise. In the spirit of better understanding what the team looks like right now, we came up with an exercise that will help analyze the fruits of the front office’s labor over the past few weeks.

Two things deserve to be called out before going any further. First, the Bucks have already established themselves as a capable regular season team but have come undone in the playoffs, so our analysis is going to skew heavily towards how impactful Milwaukee’s offseason additions can be in the postseason. The regular season still matters, as it’s the path to even get to the postseason...it just matters less by comparison.

Second (and more importantly), each and every move the Bucks could possibly make is centered around creating a vehicle for Giannis Antetokounmpo to be successful, which is what Milwaukee needs in order to convince him to re-sign and commit to the franchise long-term. It may be the case that the supermax is already in the bag, if you choose that perspective when interpreting the news that the Miami Heat have worked out a Bam Adebayo extension, which would cut into the Heat’s cap space next season and may indicate that Pat Riley does not believe acquiring Giannis next summer is feasible. However, nothing is official until it’s officially official, which is the responsible approach for all parties, and the one we gravitate towards most.

The Method

To attempt to give a rating to each of the Bucks’ offseason moves, we evaluated the player the Bucks added, how well they fit the Bucks’ vision, and how much it cost (in terms of both dollar value and what was used) to acquire them. We rated each category on a scale of 1-5 (including half-points) based on the context surrounding each player and the avenue through which they were added. After all, the haul that netted Jrue Holiday is very different than a minimum contract that brought in Torrey Craig, even if the roster spots between the two are equal. The scale was completely subjective, but we’ll get into the justification below for each player. Without further ado, here’s the scale and categories we used:

Scale
  1. Awful, tough to do worse
  2. Bad, a necessary evil
  3. Average, about what is expected
  4. Good, definitely beneficial
  5. Elite, tough to do better
Categories
  • Talent (offense)
  • Talent (defense)
  • Fit (offense)
  • Fit (defense)
  • Price (contract)
  • Resources (cost of acquisition)

The Results

Offseason Overall

It appears that offense was the major priority for general manager Jon Horst. It should not come as a surprise, considering how poorly the Bucks scored against the Heat last year and the Raptors two years ago. Of all the players added, only two of them project to definitely perform at a below-average level on offense (and neither Craig or Diakite figure to be linchpins of the roster). How much will this priority affect the defense? Only Mike Budenholzer can answer that question, and there is no clear answer at this point. Eric Bledsoe was a cornerstone of the Bucks’ league-best regular season defense, although Jrue Holiday is the rare player who can boast just as much acumen on that end of the court.

All things considered, the Bucks did close to their best with what tools were at their disposal. Speculation in league circles indicates that the Bogdanovic sign-and-trade fell apart through no fault of the Bucks or Sacramento Kings, which stands to reason since neither team would want a trade each side agreed upon to fail. Whether the Woj tweet that rocked the Bucks’ offseason stemmed from information leaked from Bogdanovic’s agent or other league executives who sought to undermine Milwaukee remains to be seen. Regardless of the reason, the deal failed and the Bucks quickly pivoted to Plan B.

In general, five of the Bucks’ new arrivals will likely take a place in the regular season rotation (Holiday, Craig, Augustin, Portis, and Forbes), and will need time to mesh with the team’s mainstays (Giannis, Khris, Brook, Donte, and the returning Connaughton). This level of turnover is difficult to manage for any team, much less one with championship aspirations, and a condensed 72-game season (taking place during a still-unconquered coronavirus pandemic) will make it even more difficult to establish a rhythm by the time the postseason rolls around.

Jrue Holiday

Holiday’s reputation across the league is built upon his defense, having been recognized by two appearances on the league’s All Defensive team. However he has a polished offensive game, as evidenced by my new favorite scouting video.

In all seriousness, in terms of both talent and fit, Jrue Holiday was probably the best player the Bucks could have added this offseason, and they managed to flip Eric Bledsoe in the process. Where we once worried about Bledsoe’s decision-making and tendency to become a shell of himself in the postseason, we can now take solace in knowing that the more versatile Holiday is now in the driver’s seat. Jrue’s not a knock-down three point shooter, but he’s generally more reliable than Eric was and (more importantly) has a much more consistent resume when it comes to scoring in the mid-range and creating easy baskets for others.

Holiday has been one of the most consistent facilitators over the past five seasons with being just one of seven players to reach 375 assists or more in each campaign as well as being one of nine to total 2250 assists during that period. Among that last group, five players have scored more points, but there’s absolutely no shame in trailing Russell Westbrook, LeBron James, Damian Lillard, Kyle Lowry and James Harden.

You may be thinking Holiday’s command of the offense contributes to these numbers, but Holiday’s usage percentage trails all but Lowry significantly during this stretch, and this season 52 players have a higher usage rate than Jrue in a minimum of 500 minutes of action including Dillon Brooks and Jaylen Brown.

The main downside when it comes to Holiday is how much it cost to get him and how much it will cost to keep him. His contract ($26.1M this season) is about what you’d expect for someone of his caliber (averaging 19/6/5 across the past 3 seasons), but his player option ($27.0M for next season) makes it more mechanically difficult to work out an extension if he’s interested in that, which most guards 30 and older are. Beyond the actual salary, the biggest gamble Milwaukee took was sending a treasure trove of draft assets to New Orleans, including two future unprotected first round picks and two pick swaps. In the event that things bottom out (which doesn’t seem likely today, just as being a Finals contender didn’t seem likely five years ago), Milwaukee will be staring at a long, dark tunnel to venture through before they’re ever relevant again.

The downside is scary, but the upside is worth it, if it ends with Giannis and Jrue committed to Milwaukee long-term, and a handful of champagne-fueled parades featuring a certain golden trophy to boot.

Torrey Craig

It was a long road to end up here for Torrey Craig. He’s been in the league for only three years but will turn 30 by the beginning of this season, and is one of the few players who have made the jump from two-way contract to standard NBA roster spot. After four years in Australia and New Zealand, he returned stateside and found a place in the Denver Nuggets rotation, earning his minutes as a tenacious wing defender. He combines his forward-sized frame (6’7”, 220 lbs) with a nearly seven-foot wingspan and guard-level quickness to disrupt drives, passing lanes, and shot attempts.

The story on defense sounds divine, but everything is inverse on offense. Craig is a career 32.0% shooter from deep and a career 66.0% shooter on free throws, making the rare offensive possession where he is asked to score a difficult proposition. Over half of his shot attempts are threes, at least, so he can at least fit in on the Bucks’ offense, but his offensive limitations could undermine his quest for consistent playing time. From Denver Stiffs:

Make no mistake, his defense is very much needed on this team, but defense and offensive rebounding are essentially where his value ends. Like I said, Craig is who he is at this point in his career, but what he is on the offensive end of the ball is a guy who shoots below league average from three, doesn’t have the ball handling skills or quickness to routinely beat players off the dribble and often can struggle finishing at the rim. He’s got great chemistry with Nikola so he’s a frequent the recipient of an easy bucket thanks to a good cut and pass but he’s never going to be a weapon on that end. In fact, he’s often the player opposing defenses elect to leave open and that caused issues for Denver in the playoffs where Torrey shot just 26.2% from three.

All that said, inking a player who exudes as much energy and intensity on defense for a minimum deal is an excellent use of the Bucks’ roster spot and salary resources, especially in light of Wes Matthews’ departure for Los Angeles. Besides Holiday, the Bucks don’t have a “wing stopper” they can afford to throw at opposing stars to slow things down. Craig may not necessarily be a steady part of the rotation (although if he shoots well enough to win the starting SG role, the Bucks lineup of Jrue-Craig-Middleton-Giannis-Brook would be as imposing as any lineup in the league), but he will bring the effort where it counts.

Jordan Nwora

When the NBA Draft drew near, the Bucks were hard-pressed to add a difference-maker with the Pacers pick (#24 overall). After giving that pick up in the Jrue Holiday trade, the chances of bringing in someone who could contribute right away were even slimmer. As luck would have it, Milwaukee didn’t just get a guy, they reportedly got their guy.

Nwora was a first round prospect back in 2019, before an injury forced him to pull out of the combine, so it’s not unreasonable to see how Milwaukee would want to draft him in the first round, and as a 22 year old junior out of Louisville it makes sense how he was still available in the second. Milwaukee needed to use second round picks (and their low salary obligations) to fill out the roster, and acquiring a plus-shooter in Nwora is a great use of that resource. In the group of players picked in his range, he was considered one of the most NBA-ready, and he will have the opportunity to make an impact very soon. Given how safe of a pick he was at the late point he was drafted, Nwora scores highly in this exercise.

Bryn Forbes

Everything we said about Torrey Craig applies to Forbes, just in the inverse. However, Forbes has the benefit of youth (only 27 years old, and 4 years in the league) and more significant NBA experience (started 143 of a possible 145 games in the past two years). He’s an excellent shooter (40.0% from three on his career) and can do just enough playmaking to justify his minutes alongside higher-usage teammates. But does is his poor defense able to be justified as well? From Pounding The Rock:

Regardless, starting Bryn Forbes while an all-defensive caliber guard like Derrick White played second fiddle is perhaps the greatest head-scratcher of the season. Not only did the undersized wing start 49 more games than White, but he also logged more minutes than anyone not named DeMar DeRozan or LaMarcus Aldridge. To make matters worse, he was arguably the worst perimeter defender in the conference.

These details suggest that it was easier for the Spurs to let Forbes walk than may have otherwise been thought, but the Bucks are on a different plane of defensive existence than the present-day Spurs. Mike Budenholzer has experience hiding poor defenders (most notably Kyle Korver), indicating that the trade off was worthwhile for floor-spacing and shot-making on offense. Considering Forbes fits that mold and was available on a minimum deal, his offensive upside and bargain-bin cost makes him a valuable addition to Milwaukee.

D.J. Augustin

For years now, Augustin has been a point guard Bucks fans have pined for. I have been one of those fans, having identified Augustin as a guard worth pursuing this offseason back in September:

Orlando relied on Augustin for offense as a backup to Markelle Fultz, and though he’s undersized (5’11” and 183 lbs.) and an older player (he’ll be 33 next season), Augustin is the type of quick-twitch ball-handler that the Bucks could really benefit from. He earned high grades in this exercise across both the regular and postseason, by virtue of his P&R expertise (over 50% P&R BH frequency, both before and during the bubble) and ability to protect the ball (AST/TO ratio of 3.05). He’s coming off of a deal that paid him $7.25M annually, so it’s hard to know what his range is...but the Bucks ought to kick the tires and find out, if he could be added as a scorer off the bench.

To obtain him, Jon Horst chose to use the non-taxpayer midlevel exception, which means two specific things. One, Augustin commanded a salary higher than $5.7M (the taxpayer MLE), which was confirmed when we learned that he landed a deal for 3 years and $21 million. That’s a lot to pay a 33 year old guard, but at least the third year is unguaranteed. Second, it introduced the hard cap to the Bucks this season, limiting them to spending only up to the tax apron level ($138.9M) on salary for the entire year, and not a dollar more. Given that they only came to the agreement on the second day of free agency, it’s reasonable to assume that the front office pursued alternatives for the MLE before deciding to devote the resource to Augustin.

Augustin, especially at this stage of his career (entering his 13th NBA season), has definite flaws. His size leads to disadvantages on defense. He takes a lot of his shots on the move, which are generally less accurate by default. He’s coming off a down year where he shot below 40.0% from the field. However, he’s a known commodity and provides a layer of diversity to the offense where the Bucks lacked dynamism. That last part was a glaring absence in Milwaukee’s offense in year’s past, and will be a welcome change going forward.

Sam Merrill

One of the most polished prospects in the draft, Merrill was widely considered to be a late second round pick because of his age, his projected defense in the NBA, and the lower level of competition he excelled against in college. The NBA Draft places a premium on players who have yet to reach their ceiling, and it’s likely that Merrill is already developed as much as he can. He spent four years in the NCAA and at 24 years old, he’s already likely done growing, so teams were less interested in dedicating draft assets to him.

The Bucks drafted him because of his plug-and-play potential on offense. Merrill is an outstanding shooter and an underrated passer, and while he’ll never be the focal point of an NBA offense he’s skilled enough to contribute in a variety of ways and can be relied upon to make the right play. That level of polish is rare at his tier of second round selections; the only other player that comes to mind and resembles Merrill’s skill level is Isaiah Thomas.

But like Thomas, Merrill’s questions are on defense. He has adequate SG size but played mostly against competition that will never take an NBA court, and there’s little reason to believe he has untapped potential on that end. Then again, some experts paint a more positive picture of Merrill’s defense, including The Stepien:

Merrill has shown some solid technique getting around screens (on-ball in the pick-and-roll & off-ball chasing around screens) although he can be slow at times. He’s able to get low and get around screens. Additionally, he also showed solid off-ball denial skills. During handoffs, he was able to get his hand in there to deflect the ball for some steals, which led to easy buckets.

If this is indeed the case, Merrill’s offense won’t have to be elite in order to outweigh his weaknesses on defense, and he stands a solid chance to outperform his draft slot. He’ll still need to compete for playing time in the backcourt, but his shooting prowess and versatile offensive game may come in handy for Milwaukee, and maybe even sooner than anyone thinks.

Jaylen Adams

Adams was a member of the Wisconsin Herd last season and was a runner-up to G-League MVP Frank Mason, Adams’ teammate and two-way predecessor who had his qualifying offer rescinded and is now an unrestricted free agent. So why did the Bucks let Mason walk and retain his number 2 in Adams? For one thing, Adams boasts superior NBA height (6’2” vs. 5’11”) for a point guard, and Mason has been extensively evaluated by the Bucks on an NBA court while Adams hasn’t. A two-way contract will be more important this season than in previous ones, though, because of the timeline for COVID-19 to get back under control, and the Bucks probably value someone who offers more scoring punch in that role than the undersized Mason.

Mamadi Diakite

Speaking of two-ways, Diakite appears to be the opposite of Adams in many important ways. Adams is a known quantity, while Diakite is more of a project, Virginia pedigree notwithstanding. Standing at 6’9” with a 7’3” wingspan, Milwaukee took a chance on Diakite as a center prospect, hoping that his instincts and quickness can be paired with improved bulk and strength to survive on the NBA floor. He does at least have one thing that Bucks bigs need to have: a three-pointer. Diakite has been developing this shot, but shot 36.4% in his last collegiate season and should be able to stretch to NBA range.

Why did he fall in the draft? In general, he did well in the Virginia system but was allowed to fill a specific role without too many complications. He’s a bad passer and ball-handler, even by center standards, and is generally considered a play-finisher with very little other upside, especially at 23 years old. Furthermore, he needs more time to physically develop into someone who can handle the physicality of the pro level. If he does that, though, he might turn out to be a gamble that pays off.

Bobby Portis

Portis was one of the most surprising names of the Milwaukee offseason; his name was not mentioned in rumors, probably for a few reasons. For starters, he’s an awful defender, and has been for quite some time. Portis never projected as more than an average defender, though his stints with the Washington Wizards and New York Knicks do suggest that there’s some measure of environmental impact on his performance. From Posting and Toasting:

Portis was meant to fill in a slot somewhere alongside fellow tall guys like Mitchell Robinson, Julius Randle, Taj Gibson and Marcus Morris, and from the get-go it was obvious that there wasn’t really a defined role for him to play. He’s a solid shooter but isn’t lights out, and he’s got skills in the post, but can be inconsistent and a little ball-hoggy.

Still, Portis made the most of his minutes, which sometimes was good for the team and sometimes detrimental. In the grand scheme of things it didn’t really matter; the Knicks were never close to sniffing the playoffs this year.

His time in New York made him a surprise addition for another reason: his contract. The Knicks whiffed on any notable free agents before they signed Portis to a two-year, $31 million contract in the summer of 2019, and even though the Knicks exercised their team option on Portis, going from making above $15M to below $4M is quite a drop, and not one usually expected in the NBA.

A third reason he was a surprise signing is his player profile: Portis is at his best playing with the ball in his hands, and has shown signs of three-level scoring ability by taking advantage of mismatches against other bigs in the league. Considering the Bucks’ most recent PF backup was Ersan Ilyasova, it’s safe to say that Portis doesn’t fit the mold. But as we have stated elsewhere, non-Giannis shot creation in the postseason is an important difference the Bucks need to maximize this year, and Portis brings that ability to bench lineups. As long as he can survive on defense...

Pat Connaughton

We have gotten to know Pat Connaughton as a player relatively well over the past two years, so we don’t need to belabor the points about what he’s good at (cutting, dunking, sometimes shooting) and what he’s not (staying under control, shooting consistently). He is definitely decent value on a minimum-level contract, considering he’s roughly a league-average player in terms of general impact. As a result, you can imagine the outcry when Bucks fans learned that he would be receiving a salary well above the league minimum, and then later learned that there apparently was a mix-up and that his salary had increased alongside the length of the deal!

The devil is in the details! Apparently, the original offer (2 years/$8.3M) included a player option on the second year, which was discovered to be impermissible under the Early Bird Rights provision of the CBA. So if the Bucks stuck with their existing offer, they would have used a little less than half of their available MLE funds and precluded themselves from signing DJ Augustin, or anyone else for that matter!

This would have been disastrous. Using a roster spot on Connaughton is fine, and giving him a slight raise is even acceptable given the number of minutes he’s played. But using your MLE resource when you flat-out don’t have to (the Early Bird exception allows a team to re-sign its own player to a higher salary without using cap space, similar to a veteran minimum deal) would be a massive blow to the Bucks’ offseason efforts, and it cost them both money and guaranteed years when it came to rectifying the mistake.

To be clear, though, this is not an unforgivable error. The biggest impact of the Connaughton deal is the fact that the higher salary caused Milwaukee to have less space under the hard cap (by virtue of Jrue Holiday’s incentive, explained here) and are unable to sign anyone to their remaining 15th roster spot without making a deal that sheds salary elsewhere. And that higher salary may have actually been due to (gasp) demand for Pat’s services! Zach Lowe reported in a conversation with Brian Windhorst that Connaughton had been gaining attention from teams with cap space for a deal between $5-6 million; had the Bucks not fielded their own competitive offer, Connaughton could have walked for nothing.

Some Bucks fans may have preferred that outcome, but the question that still deserves an answer is this: who would be a decent replacement if Pat left? The Bucks were still over the cap and were set to use their MLE on Augustin and their BAE on Portis; what minimum-level contract would attract a wing who is at least as good as Connaughton is (much less one who has such a strong relationship with Giannis)?

All in all, the Connaughton re-signing is an issue, but not an existential one. The Bucks’ still managed to fill out the spots in their rotation with players who should demonstrate they deserve to be there, and Connaughton should not immediately be one of those primary options. All teams are going to make mistakes, and the Bucks were at least able to correct theirs without any lasting effects (that we know of).

Bonus! Bogdan Bogdanovic

Sometimes the worst thing that can happen is knowing what might have been. We examined why the Bogdanovic sign-and-trade fell apart thanks to a single tweet from a prominent ESPN reporter, and subsequent reporting has shed more light on how things unraveled. The main takeaway is this: the Bucks and Kings agreed on a deal in principle and were prepared to follow the steps to execute the deal, including opening contract negotiations with Bogdanovic on Friday, when free agency opened up. But once the cat was let out of the bag on Monday night, other teams began playing defense. Per Bleacher Report (emphasis mine):

[A]t least one rival team filed a formal complaint to the league office Wednesday, sources said. And by that afternoon, the league informed both Milwaukee and Sacramento that it would open an investigation into an alleged sign-and-trade already being agreed to four days before free agency had begun. The league also sent a memo to all 30 teams that afternoon reminding franchises of the NBA’s anti-tampering policies, encouraging teams not to “jump the gun” in contacting players under contract with other teams and warning punishments of up to $10 million and draft-pick forfeiture. At that juncture, it became clear Milwaukee was no longer a possible landing spot for Bogdanovic.

So, there you had it. Whether it was because of a premature media report, a two-faced agent angling for more money, or interference from another franchise, or some combination thereof, the Bucks did not bring in Bogdanovic. What’s more frustrating is that people treat it as a failure on the part of the Milwaukee front office, when every report and rumor suggests that they did the right thing. Something happened here that was outside of the Bucks’ control, and for reasons unknown (nefarious or otherwise), Milwaukee pivoted to Plan B and went the route of signing everybody we previously outlined.

It’s a real shame too, because landing someone with Bogdanovic’s level of skill and grit in exchange for Donte DiVincenzo and some expiring salary was an absolute coup for Milwaukee in terms of value. The fact that the Kings didn’t match a significant (but bearable) offer sheet from the Atlanta Hawks shows just how much better the Bucks deal would have been for the Kings, rather than losing Bogdan for literally nothing. But the win here goes to whichever franchise(s) decided to play dirty by virtue of invoking the selective enforcement of the NBA’s tampering rules. Bogdanovic would have been a great fit for the Bucks’ offense, a passable defender who could be adequately covered for, and a fairly-paid contract that could have still allowed the Bucks to make most of the moves they ended up making anyway. The fact that he isn’t speaks volumes about the NBA, not the Bucks.


If you made it all the way to the end, congratulations. This was a long one but should hopefully last you through the holiday, and all attention from here until training camp will be focused on the constant “will he/won’t he” surrounding Giannis’ supermax extension. He’s the bedrock of the franchise, but he can’t do it alone, and we hope this overview of his teammates helps illustrate the success he can find in Milwaukee this season.