In this country, you gotta make the money first. Then when you get the money, you get the power. Then when you get the power, then you get the women. – Tony Montana, Scarface

Admittedly, the quote needs a little contextualization. The quote suggests that things happen in sequence, and the only way to get where you want is to take things a step at a time. That’s exactly what the Bulls need to do in this series. They want Cleveland, but they’ve got to go through Milwaukee to get there, and the Bucks are just good enough to give them a run for their money if they aren’t focused on the task at hand. On the flip side, the Bucks have come a long way this season after having the worst record in the NBA last season. Managing to claim the six seed in the playoffs, even in a weaker conference, is a huge improvement after only winning 15 games the previous season.

Backcourt Matchup

The midseason acquisition of Michael Carter-Williams was an enigmatic one, but he certainly fits Jason Kidd’s defensive scheme. Offensively, the reigning Rookie of the Year is not a good perimeter shooter, to put it mildly, but is effective at the basket. He is an exceptional rebounder from the point guard position, and his size and length give him an inherent advantage defensively.

Khris Middleton has surprisingly emerged as a legitimate primary scoring option for the Bucks and even hit a few clutch shots in the regular season. The Greek Freak is also a tough matchup for anybody. At 6’11”, shooting a three-pointer over him or MCW is like trying to shoot it over a palm tree. The long-armed duo is also active in passing lanes, and creates a ton of turnovers that lead to transition buckets at the other end. Giannis Antetokounmpo still needs to refine his game some on the offensive end, particularly his jump shot. He is a frightening fast break dunker, and shoots a good percentage from the field because of his ability to get to the rim though. The Bucks also get decent bench contributions from O.J. Mayo and Jared Dudley.

For the first time in a few years, the quality of the Bulls’ backcourt isn’t predominantly dependent on the health of Derrick Rose. Don’t misunderstand, a healthy Rose is a huge value added for the Bulls, but the emergence of Jimmy Butler as a two-way star eases the burden on Rose’s shoulders. Aaron Brooks is also playing well as it seems that Thibs is carving out a niche as the “undersized point guard whisperer”. Tony Snell and Kirk Hinrich also provide solid bench minutes for Chicago. Hinrich has carved out an exceptionally impressive resume as a bench player for what feels like a decade.

Edge: Bulls

Frontcourt Matchup

This is where the Bulls need to really attack the Milwaukee defense. In October, Pau Gasol shredded the Milwaukee frontline for 46 points and 18 rebounds. Chicago needs to try to get him going early in the series. Joakim Noah hasn’t really looked himself this season, but he’s still a good player and an exceptional post passer. Mike Dunleavy is a replacement level starter at this point in his career, but the bench production of rookie Nikola Mirotic combined rim protection from Taj Gibson when Pau takes a rest makes up for Dunleavy’s diminishing contribution. Mirotic has been so good that even as a bench player he is almost a lock to finish in the top three of the Rookie of the Year voting.

As for the Bucks, the frontline is the weakest link on the team. Ersan Ilyasova is soft, and he looks like one of the Franco brothers, right down to that infuriating smirk. He’s athletic and a pretty good shooter, but he will get owned by Pau on Bulls’ possessions (and Pau isn’t the toughest player in the NBA by any stretch). Zaza Pachulia has played fairly well for the Bucks, and is consistently voted one of the dirtiest players in the NBA. The odds that he has made Ilyasova cry in practice are -400. Off the bench, John Henson is a solid post defender, but doesn’t provide much on the offensive end.

Edge: Bulls by a lot

Coach

Tom Thibodeau is one of the best coaches in the NBA to not have a ring as a head coach. Jason Kidd is one of the best young coaches in the league, and has made the transition from point guard to head coach much more smoothly than Derrick Fisher. However, Thibs has to get the nod in this one for now.

Edge: Bulls by a little

What an upset might look like

The Bucks are one of the most efficient defensive teams in the league, and one of the best transition offenses in the league. If the Bulls don’t take care of the ball and shoot poorly, then they will lose a few games in this series. Pair that with some Khris Middleton heroics and better than usual post play and you have yourself an upset.

Prediction

There were too many implicit (and one explicit) “ifs” in the above section. Bulls lose one, but wrap it up in five.