What does Damian Lillard joining the Milwaukee Bucks mean for the Boston Celtics?

When Giannis Antetokounmpo sits down to have his next plate of Oreos, he’ll be washing it down with a hefty glass of Miami Heat tears. After falling to the eighth-seeded Heat in the first round of last year’s playoffs, the most brutal loss of his career, Antetokounmpo helped steal Pat Riley’s golden goose.

Damian Lillard is headed to the Milwaukee Bucks.

But while Milwaukee celebrates and Miami copes, Boston Celtics fans are likely stuck in the middle. On the one hand, the Heat didn’t get Lillard. That’s a win. On the other, the Bucks did. That, not so much.

What does this mean for the Celtics’ chances in the East? How much better are the Bucks? What happens with Jrue Holiday, and could he find his way back into the conference?

The question of “When and where will Lillard get traded?” has been answered, but in its wake are a million more left to be tackled.

Kicking things off, the only way to answer the query of what Boston’s new chances in the East are is to take a look at Milwaukee and assess what this addition means for their season(s).

It’s important to note that while Lillard is an excellent addition and will fit in great alongside Antetokounmpo, Khris Middleton, and Brook Lopez, the loss of Holiday will absolutely be felt. He just wrapped up his best season in years, earning his first All-Star nod in a decade and making the All-Defensive First Team.

The Bucks were a top-four defensive team in the league last year (based on defensive rating), and losing the best perimeter defender (or one of them) in the NBA will certainly hurt their chances of reaching that peak again. They don’t have many great perimeter defenders on the roster anymore, especially since Jevon Carter also departed this summer.

However, this deal has the potential to do wonders for Milwaukee’s offense.

Milwaukee’s defensive success last season was paired with a middling offense. They ranked 15th in offensive rating and 19th in field goal percentage, and when Antetokounmpo was out, they struggled to find sources of offense, especially with Khris Middleton working his way back from an injury.

With Lillard in town, the Bucks not only have a much better secondary scoring option but also a guy who could take over as the team’s primary scorer if Antetokounmpo wants to focus his efforts on the defensive end.

Holiday is a great ball handler, an exceptional playmaker, and has shot super well from three-point range in each of the last three seasons. However, he’s nowhere close to the scorer Lillard is.

En route to their first championship last year, Jamal Murray and Nikola Jokic ran what was arguably the deadliest two-man game the league has seen in decades. Lillard’s scoring ability and Antetokounmpo’s rim pressure have the potential to create a similar threat, and that should absolutely strike fear into the hearts of every team in the East, including the Celtics.

What Boston can take solace in is how well they’ve matched up against the Bucks in recent years. Adding Lillard into the mix will give them an extra element to worry about, but with White, an All-Defensive guard, leading the way, they have guys who can hold their own against all of Milwaukee’s scoring options.

Al Horford is entering the final years of his career, but he’s defended Antetokounmpo extremely well during his time in Boston. Add in Jaylen Brown, Jayson Tatum, Kristaps Porzingis, and Robert Williams, and the Celtics’ defensive front matches up with Milwaukee’s now seemingly elite offense as well as any team in the league.

But the follow-up question that needs to be asked after a Lillard trade is, “Where does Holiday go now?”

Portland has no plans to keep the All-Star point guard, and if he joins an Eastern Conference squad, they will get a major boost. As silly as it may seem, Boston calling the Trail Blazers about a trade isn’t out of the question, though they would have to empty the picks cabinet to garner any interest.

Of all the potential East foes Boston could encounter, the Philadelphia 76ers, New York Knicks, Heat (as ironic as it would be), Chicago Bulls, and Orlando Magic seem most primed to strike while the iron is hot.

Philadelphia could use the security as they deal with the James Harden situation. The Knicks are always ready to make a splash. The Bulls desperately need point guard help. Orlando seems like they are a point guard away from being a real threat in the East.

Plenty of Western Conference teams will undoubtedly check in with Portland about Holiday as well. Still, while most Celtics fans are thinking about how Boston might deal with an Antetokounmpo-Lillard duo, the Holiday factor is still very much a storyline to watch.

The Bucks will be a force next year. But they were last season, too. Swapping Lillard for Holiday is an upgrade, but not one that the Celtics can’t prepare for. Boston still has one of the most talented rosters in the league, and this deal doesn’t change that.

Did the East get a bit scarier? Yes. Should the Celtics be concerned? Absolutely not.

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