Damian Lillard, in the midst of “the hardest transition of my life,” still faces his biggest on-court challenge yet.

The 33-year-old veteran will be held responsible for the outcome of this Milwaukee Bucks season, for better or worse, whether or not he deserves it. That is what happens when a front office trades a core member of a recent championship roster for an eight-time All-Star. He is the face of change for them.

Everything, as of now, points to the Bucks being worse than last season. At this time last year, they owned the NBA’s best record, three games better than both the Boston Celtics and eventual champion Denver Nuggets. They are entered Wednesday fifth, 10 games worse than the Celtics and trailing a trio of Western Conference contenders.

Then they moved 11 games back from the Celtics with a 122-119 loss in Boston. Lillard scored 32 points with Giannis Antetokounmpo out.

Second place in the East is not so wide a gap in the grand scheme, but it is slim enough that one tweak to a team could have meant all the difference, and much of that margin does point to Lillard as a likely culprit.

The Bucks are shooting and taking care of the ball better, as their offensive rating has risen from 113.6 (17th) at this point last season to 118.8 (4th, entering Wednesday). We can agree that Lillard has played a significant role in that.

But the Bucks are also worse at 3-point defense and defensive rebounding, as their defensive rating has slid from 109.8 (3rd) to 115.4 (16th). They have changed coaches three times in the past 10 months — from Mike Budenholzer to Adrian Griffin, Joe Prunty and now Doc Rivers — and replaced several role players (notably Grayson Allen for Malik Beasley), but no one should argue against Lillard playing a role in this, too.

Damian Lillard and the Bucks are looking way up at the Celtics in the standings. (Photo by Tim Nwachukwu/Getty Images) (Tim Nwachukwu via Getty Images)
And you rarely hear a title team talking like them.

“I feel like for me, this has been the hardest season that I’ve played — not only physically, because I had the procedure done on my left knee in the end of June,” Antetokounmpo told The Athletic’s Sam Amick. “And I had to get back to myself. … But emotionally, and mentally, it’s been draining. I’m not going to lie to you. It’s been extremely tough, from Coach Bud being let go to Coach Griff coming in, being let go, then Coach Joe for three games, Coach Doc coming in, and then you have Dame. It’s been tough.”

“It’s been harder than I thought,” Rivers said of the job three weeks into his tenure.

It is even more personal for Lillard, who opened up about a divorce that was filed three days after his trade to Milwaukee, telling Yahoo Sports’ Vincent Goodwill, “It’s probably been the hardest transition in my life.”

As Antetokounmpo told Amick, “Hopefully, step by step, I get where I want to go and I’m able to help the team get where we want to go.” The same should apply to Rivers and Lillard. There is still time left in the regular season to get right before the playoffs, beginning with Wednesday night’s showcase in Boston.

The Celtics nearly blew a 21-point lead to the Bucks in November and received a 33-point beatdown from their rivals in January. Wednesday offers another look at the matchup and whether Boston’s big moves — acquiring Kristaps Porzingis and Jrue Holiday in the offseason — outweighed Milwaukee’s big swing for Lillard. Unfortunately, that look won’t be as clear as we would have liked, since Antetokounmpo has reportedly been ruled out with a hamstring injury.

The statistics overwhelmingly favor Boston, as do other factors since Milwaukee’s 2021 title. The Celtics have won five playoff series to the Bucks’ one over the past two seasons, including a second-round series between them in 2022. Boston’s Jayson Tatum and Jaylen Brown have aged into their NBA primes, surrounded by more talent than ever before. Meanwhile, Brook Lopez has aged into his mid-30s, and a series of injuries has left Khris Middleton looking up at an All-Star field of which he was once a member.

Milwaukee’s defensive stats might be anomalistic enough to regress in its favor. The team’s defense has an admirable shot profile, forcing more midrange jumpers than all but three teams, per Cleaning the Glass. Opponents are making 44.9% of them. Only four teams allow a higher percentage from midrange. How much that has to do with the quality of those looks is difficult to discern, but the NBA’s tracking data suggests the looks are no cleaner than last season, when the Bucks held opponents to the sixth-worst percentage from midrange (41.6%).

Still, Lillard will carry Milwaukee’s drop in net rating from 3.8 last season to 3.3 this year until he proves otherwise. It may not seem like much, but when Boston has nearly doubled its net rating to a historically great 11.9, that margin feels weightier. The front office sensed it, twice changing course on its coach. You can hear in Antetokounmpo’s diatribe how difficult it’s been to build championship chemistry with Lillard.

While Wednesday’s game against Boston might be another opportunity to demonstrate strength against the East’s elite, none of it will matter if Milwaukee fails to get out of the second round again. It cannot get worse than last season, when the Miami Heat bullied the Bucks in a shocking five-game, first-round upset.

Chemistry may come with time, but Milwaukee is in a race against Lillard’s prime to maximize its window with Antetokounmpo, who gives his team a shot in any series but needs help to win four. Lillard’s 24.4 points per game are his fewest since 2015, save for the season he required abdominal surgery. His free throw are down, and his effective field-goal percentage (51.2) is his lowest since 2016, when he was 25.

Lillard will turn 34 in July, two years younger than Stephen Curry, who is the same age as Chris Paul was when he last made an All-NBA team, averaging 14.7 points a night for the Phoenix Suns. Point guards are lasting longer than ever before, but the Bucks have to wonder about the two sides of that coin: Has Lillard fallen out of the All-NBA discussion due to his difficult transition or the beginning of a steady decline?

Lillard is under contract through the 2026-27 season, when he is owed $58.6 million, the same season Antetokounmpo can opt out of the three-year, $186 million extension he signed in October. With little in the way of rising talent and no first-round picks to trade until 2031, this may be Milwaukee’s lot in life.

Of course, it’s not such a bad lot to be in. Lillard has risen to the occasion in the postseason, twiceending series by his own hand. His clutch numbers — 36.7 points (66.4 TS%) per 36 minutes and +84 in 114.9 minutes — are encouraging enough to believe he can rise again, as long as he and Antetokounmpo can find the chemistry to close games together.

Wednesday’s game against Boston was an opportunity to jolt Milwaukee through the hard part and into the hardest part of this season. Instead, it was another stumbling block, potentially on the path to a third straight playoff disappointment, where answers on the other side won’t be easy for Lillard or the Bucks.