The Portland Trail Blazers are heading home to Rip City winless following Wednesday's disappointing 107-104 loss to the Cleveland Cavaliers, finishing a quick Eastern Conference road trip 0-3.

Here are three key takeaways from another frustrating Blazers defeat.

The Wrong Kind of Dame Time

Lillard's fingerprints were all over crunch-time…just not in the way Rip City has come to expect over the last decade. Portland's franchise player reached the nadir of his ongoing slump at the worst time against Cleveland.

It started when he botched a virtually uncontested layup that would've completed the Blazers' arduous comeback efforts, tying the game with 2:30 left. Lillard didn't make excuses for another poor shooting night or his bizarro collapse in the clutch, but admitted after the game that he “irritated” a core injury in the second quarter. You can see how that flare-up could've affected his balance after he explodes past Jarrett Allen on that should've-been game-tying layup.

It didn't get better for Lillard from there.

On Portland's following trip down, he missed one of the cleanest pull-up looks from three he's had all season. Lillard cleared out the left side of the floor for an isolation against Evan Mobley 40 seconds later, failing to get a step on the rookie seven-footer then getting his scooping finger roll blocked. He atoned with a steal on the ensuing Cavaliers possession, only to throw the ball out of bounds during an odd 2-on-1 fast break with Anfernee Simons.

After all that, plus an and-1 layup right through Collin Sexton that cut Cleveland's lead to three, Lillard had the chance to knot the score again in the game's final seconds. Billups said he was pleased with the look the Blazers got after he drew up a final play in the huddle. Lillard, though, ultimately lamented drawing a switch from Allen, who managed an awesome contest on his step-back three try as time expired.

“If I had to do it again, I wouldn't have used a screen,” Lillard said. “I just would've kept the wing on me.”

Allen, who Billups called a “monster,” frustrated Portland's guards in switches all game. He's not the plodding center his laughable length makes him out to be. Even if Lillard had simply isolated on Cedi Osman, though, recent odds are it wouldn't have ended the way he wanted. He went 3-of-12 from deep against the Cavs, needing 27 shots to equal his season-high of 26 points.

Fingers crossed that Lillard's long-awaited breakout comes on Friday against the Indiana Pacers.

Point of Attack Problems

Billups almost seemed fed up with his team's defense after the game, and rightfully so. Cleveland put up a 112.6 offensive rating on Wednesday, a number that would rank top-five in the season's early going, and absolutely carved up the Blazers in the first half before Billups made several adjustments. Just like the Philadelphia 76ers, by the way, the Cavaliers were absent three key contributors. Lauri Markkanen and Kevin Love missed this game due to health-and-safety protocols, while Isaac Okoro—by far Cleveland's best perimeter defender—sat out with a hamstring strain.

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Billups couldn't help but point out that bench players and rotation replacements have been burning the Blazers of late. Two days after Georges Niang dropped 21 points, five rebounds and five assists on Portland, Cedi Osman and Dylan Windler combined for 25 points and seven triples on 12 field goal attempts. It's not just the Blazers' inconsistent back-line rotations and merely semi-frequent multiple efforts that have been an issue on defense, though.

“We're not doing a good job keeping the ball in front of us. We're getting beat too quick,” Billups said. “Our defense is designed to help and help your buddy, but when you get beat in one dribble that help can't even be there yet.”

Portland's best defensive stint came when Billups went small in the late third and early fourth quarter, slotting a rejuvenated Robert Covington and Larry Nance Jr. up front. Switching across all five positions left Portland vulnerable on the defensive glass, a weakness exploited by Allen, but kept the defense out of rotations that Ricky Rubio and Darius Garland picked apart early. The Cavs' putrid 97.9 second-half offensive rating was due in large part to the downsized Blazers keeping the ball out of the paint—and themselves from scrambling on defense.

Right when Portland brought back Jusuf Nurkic midway through the fourth quarter, Rubio got Allen a dunk, taking full, immediate advantage of soft defense at the point of attack. Making matters more discouraging? The Blazers were still switching one-through-four, ostensibly to avoid exactly this result.

Nance, to be clear, isn't the culprit Billups was indirectly referencing in his complaints above. Lillard, Simons and C.J. McCollum are Portland's biggest problems at the point of attack, in that order, and there's only so much even all-out intensity and airtight execution can do to fix it.

Neil Olshey insisted over the summer that the Blazers' personnel didn't lead them to basketball's second-worst defense last season. On Wednesday night, Billups— sure looked like he was suggesting the opposite.

Rotation Roulette

Portland's lineup from this game that will get most attention is the one that closed it. For the second straight time with his team trailing in the clutch, Billups rolled out Lillard, Simons, McCollum, Norman Powell—who was awesome all night long—and Nurkic. It didn't take the rookie head coach's post-game explanation to understand why.

“Well, we wasn't stopping 'em anyway,” Billups said. “So I wanted our offensive weapons to be out there, try to get in the pick-and-roll and then create. Wherever the ball landed at, we'd feel good about it.”

Simons, shining again offensively, came in for Nance with 3:17 remaining. Say all you want about the long-term defensive efficacy of a lineup featuring four offense-first guards—all of whom stand about 6'3”—and a massive seven-footer who can't switch, but Portland allowed just four points after Billups brought in Simons. That group managing just three points over the final three-plus minutes of a close game was the real reason why the Blazers failed to complete their comeback from a double-digit deficit.

Either way, it's clear Billups is searching for lineups that will give Portland its best blend of offense, defense and energy. Nassir Little had been first off the bench in every game this season until Monday, when he ceded that honor to Nance and Cody Zeller. Little still got first-quarter minutes against Cleveland, but fell behind both Tony Snell and Nance in the pecking order during the second half.

Snell only appeared after intermission, entering for Powell as Portland's initial sub. Though active and alert as a back-line defender in both man and zone defense, Snell didn't record a single regular box-score statistic other than a missed three.

There's nothing wrong with experimenting. This rotational numbers crunch seemed inevitable once Portland traded for Nance, and it clearly became a story against Philadelphia—when Snell made his Blazers debut. Billups will no doubt continue tinkering with his rotation going forward, even if injuries don't force his hand. But just like their penchant for slow starts that he bemoaned post-game, Billups' lineup juggling act will be an obstacle the Blazers have to overcome to get some much-needed victories in wake of an 0-3 road trip.