It was early October. Seven days after Kyrie Irving’s surprise announcement that he planned to re-sign with the Celtics and five days before the season opener. Inside a tented gazebo at the Westin Boston Waterfront, members of the Celtics organization mingled with VIP guests before the start of the team’s annual Shamrock Gala.

In one corner of the room, Kyrie Irving lounged on a swanky sectional sofa, looking relaxed and content. Around him, members of the organization all seemed to be smiling. There was an excitement that lingered from Irving’s declaration and the anticipation for the season set to tip.

Before the night’s program began, Celtics co-owner Wyc Grousbeck stepped in front of the assembled media and beamed when asked about Irving’s impromptu announcement about his future and the potential of this year’s group.

“In terms of the relationship with Kyrie and the Celtics and his teammates, this bond between these guys, I think is the real deal,” said Grousbeck. "I've seen 16 rosters now and this team is knit together. They're a real team and they're taking a great approach to this season.”

The conversation shifted to what Grousbeck wanted to see this season and he laughed before pointing to his 2008 championship ring. “I want to see — someday — one of these again.” He quickly clarified that he simply wanted a sustained run as a title contender but the insinuation was clear: The 2018-19 Celtics had lofty expectations.

For the past six months, smiles were harder to come by around these Celtics. The burden of expectations weighed heavy on Boston throughout the season and the Celtics never quite figured out how to harness their collective talents. The team became a chore to watch, regularly devolving into bad habits and then bickering about the reasons for their failures. And Irving’s uncertain future has hovered over the team throughout the season — and will only intensify this summer.


How exactly did everything go awry? Let’s take a look at some of the defining moments of the 2018-19 season.


Sept. 24, 2018: Ready for their close-up
As Boston players navigated their Media Day chores on the eve of training camp, the Celtics culled together Irving, Gordon Hayward, Jayson Tatum, Jaylen Brown, and Al Horford for a photo shoot. This wasn’t an accident. Boston’s projected starting five — affectionately dubbed the Newport 5 in this space and dubbed Erotic City by others — was supposed to be the answer to any of the star-studded groups the Warriors might trot out. This was supposed to be the lineup that differentiated the Celtics from their Eastern Conference competitors. Instead, it fizzled mightily as Boston stumbled out of the gates of the season.

Maybe we should have been paying more attention to coach Brad Stevens on Media Day as his words were prescient when the first question of the day asked him about the expectations for the new season. Said Stevens: "I think when you break down last season, first of all, we had a really fun team and a team that really pulled together...We have some real areas to improve [on both sides of the ball], otherwise, we’re not at the level we want to be at. And so we’ll see if we put in the work, defensively, and we’ll see if we improve offensively.”

Oct. 6, 2018: A (pre-)reason for concern
The first caution flags went skyward as the Celtics staggered through a 1-3 preseason. It wasn’t so much the record but the way the Celtics were routinely outworked in those games. Still, it seemed foolish to overreact to preseason basketball and much of the concerns were written off to 1) A shortened training camp before diving into game action and 2) Rust and reintegration of star players (though Irving certainly seemed to hit the ground running). After a loss in Cleveland to wrap the exhibition slate, Al Horford expressed concern while noting, "We have a lot of work ahead. That’s just the reality of it. No excuses. We have a lot of work to do.” Stevens yet again maybe saw what lied ahead when he said, "I just want to play with spirit and passion and togetherness, and we just have to find that kind of joy in playing together.”


Irving’s declaration that he planned to re-sign in Boston at a season-ticket holders’ event, combined with both a long break before the start of regular-season games and an opening-night trouncing of the Sixers restored a bit of confidence in these Celtics. But it was fleeting.

Oct. 22, 2018: Searching for their Magic
A loss to a Kawhi Leonard-led Raptors had reminded Boston that the East wasn’t going to be the LeBron-less cakewalk that many anticipated over the summer. But it was a home loss to the Magic in the fourth game of the season that made everyone wonder if the preseason wasn’t just a fluke after all. Following the loss, Irving was asked about where the team’s chemistry stood. His response: "I don’t know. I don’t know. I don’t mean that negatively. I just don’t know. It’s four games. I don’t know. I don’t know. I don’t have the answer for that.” Irving also offered his first glimpse into the difficulty in getting everyone on the same page when he added, "Being on a team like this, where it’s a challenge for me to figure out where do I fit into all this and how do I lead this team the best way I can with other great players. So it’s all a learning experience.”

A 6-2 start, culminating with a win over the previously undefeated Bucks, had the Celtics feeling good about some early bumps in the road. The team then labored through a 1-4 road trip that started with Victor Oladipo hitting a game-winner over Irving. Boston’s only win on the trip required a double-digit comeback and a Marcus Morris overtime winner.

Nov. 11, 2018: Smart: ‘I probably hate losing more than I love winning'
After the Celtics stumbled their way through a disappointing trip, Smart unloaded on his teammates after a loss in Portland. In a locker room outburst, Smart demanded that the team stop making excuses for their streaky play. "I hate losing. I probably hate losing more than I love winning,” Smart told NBC Sports Boston in the aftermath. "Especially with the team that we have and the potential that we have, we shouldn’t be losing games that we know we should win. Let alone, getting down 20 early and putting more pressure on ourselves and more stress on ourselves to come back.” Added Smart: "We have to look ourselves in the mirror, look at one another, hold each other accountable, and figure out what’s going on.” Irving compounded matters by wondering out loud if the Celtics might benefit from having a 14- or 15-year veteran to help steer Boston’s young roster.


A thrashing of the Bulls and an overtime win over the Raptors sent the roller coaster on the upswing but a plunge quickly followed with a three-game losing streak, including an early candidate for worst loss of the season when the Knicks came to town. Hunting for a fix, Stevens moved a struggling Hayward to a reserve role before a loss in Charlotte.

Nov. 21, 2018: Expectations ‘means s--- at this point'
Trey Burke gouged the host Celtics to the tune of 29 points and 11 assists in 32 minutes as the four-win Knicks won a game that even they didn't want to win. After the Celtics dropped to 9-9, Irving noted, “The expectations everyone has on us means s--- at this point. Excuse my language but it doesn’t mean anything. Until we figure that out, we’ll be struggling. But I’m going to continue to push this team, I’m going to continue to lead the best I know how, as well as with Coach Stevens.”

Nov. 24, 2018: Time to get Smart
Another poor outing, this time in a loss in Dallas, left Smart fuming again. He deemed himself speechless but did his best to put his frustrations into words. "It’s like déjà vu all over again. Like, we keep saying and doing the same thing after every game. It’s getting really annoying. I don’t even know why to say to [reporters] at this point,” said Smart. The loss spurred more change from Stevens, who shuffled Smart into the starting lineup and moved Brown to a reserve role.

The Celtics put together some of their most inspired ball of the season in the aftermath of Smart’s elevation, winning eight straight games. But it wasn’t enough to chase away the drama.

Dec. 21, 2018: Team meeting hoping to Buck the trend
Even as the Celtics piled up wins with a new-look starting lineup, it was fair to wonder if they were feasting on inferior competition. Even after a couple of bad losses (including another unforgivable home loss to the lottery-bound Phoenix Suns), the Celtics found a measuring-stick game against the Bucks. Giannis and Co. promptly snapped a ruler straight over their backs while rumbling to a double-digit win. That triggered what would become a very publicized closed-door meeting for the Celtics. While initially barking that the meeting was, “none of y’all's business,” Irving later noted, "Much needed. I think everyone can see that we’ve obviously had some inconsistencies regarding our play so I think it was just time to address it.”


The Celtics won seven of their next nine, prompting the latest round of, ‘Have they figured out what ails them!?’ There were encouraging signs along the way, too, such as a 35-point night for Hayward, which led to another round of, "Has Hayward turned the corner?!" Spoiler alert: No, to both questions.

Jan. 10, 2019: Push comes to shove
When Brown failed to sprint back on defense during the second quarter of another listless loss in Miami, Morris took exception and tempers flared. On the bench during a timeout, the two exchanged words before Morris shoved his younger teammate. The dustup was filmed by a fan seated behind the Boston bench and the video went viral. Morris and Brown downplayed the incident in the aftermath, chalking it up to frustrations, with Morris adding, "I know social media is going to make a big deal about something like that, but I feel as though I’m one of the leaders on this team, so if I have an engagement with any of my teammates we all know that it’s basketball related and it goes nothing past the court. It’s just two guys that both care about the game and that’s all it was.”

Jan. 12, 2019: Not exactly the happiest place on Earth
On the final play of a game in Orlando, the Celtics didn’t get the ball in Irving’s hands and he didn’t mask his displeasure. After the buzzer, Irving stomped at inbounder Hayward, incredulous that the pass instead went to Tatum (who missed a game-tying fadeaway with a decent look). After stewing a bit as the visitor’s locker room cleared out, Irving dismissed his first few postgame questions in minimal words. Then he unloaded, particularly on Boston’s younger players. Said Irving: “Experience … we’re lacking it and, because of that, we have a lot of learning to do.” Later he added, "We had nothing to lose [last season] and everybody could play free and do whatever they wanted and nobody had any expectations. We were supposed to be at a certain point, we surpassed that. Young guys were supposed to be at a certain point, they surpassed that. We come into this season, expectations, and it’s real. Everyone from the coaching staff to the players, it’s very much real every single day, so, that’s new. It’s tough. It’s hard.” 

Jan. 14, 2019: No finger-pointing!
Before the team's third consecutive loss in Brooklyn, Irving admitted he probably shouldn’t have pointed fingers after the Orlando loss. But Brown still fired back after the game. Said the third-year swingman, "We've just got to have each other’s back at the end of the day. We can’t make comments. We can’t point fingers. We've just got to continue to empower each other and have each other’s back.” That push back might have forced Irving to further consider his leadership style but it was far from the end of the drama.


Jan. 16, 2019: ‘I had to call Bron’
Irving put together one of his best nights in a Celtics uniform, registering 27 points and 18 assists in a win over the Raptors. Then, rather unprompted, he revealed in his postgame media session how he phoned former teammate LeBron James to apologize for the way he acted when he was a “young player” in Cleveland. If Irving thought the revelation would accentuate his quest to be a good leader, it backfired when some wondered if Irving was pining for a reunion with James and throwing the young players under the bus in the same breath. What Irving seemed to be doing was not only reconciling with his past but recognizing that he didn’t want to become James, the sort of heavy-handed leader that drove him away from Cleveland. Instead of letting his play do the talking in a statement win, the revelation only caused Irving’s leadership missteps to linger in the spotlight.

The Toronto win kickstarted a stretch in which the Celtics won 10 of 11, the only loss being a hard-fought defeat at the hands of the visiting Warriors. Boston even clawed itself from the No. 5 seed it seemed stuck in for weeks and briefly surged to No. 3 in the conference. What could possibly kill Boston’s good vibes? An unexpected Anthony Davis trade request.

Feb. 1, 2019: 'Ask me July 1'
When Davis’ camp tried to power play The Brow's way to the Lakers before the trade deadline, the Celtics suffered collateral damage. First, the trade request reopened the national debate about whether the Celtics should be willing to include Tatum in a potential deal, which forced Boston’s 20-year-old to deal with questions about his own future. Irving also got dragged into the mix when reports suggested he wasn’t a slam dunk to re-sign in Boston this summer, forcing Irving to address his future for one of the few times since his preseason declaration. Irving, already irritated by the speculation, grumped his way through a media session in New York (of all places) where he responded to questions about his future by declaring, “Ask me July 1.” He added, "Obviously, Boston is still at the head of that race,” but it only hammered home that this wasn’t the one-team sprint that many thought after his preseason declaration.


Feb. 7 + Feb. 9, 2019: La La Bland
Even amid all the Kyrie drama, the Celtics were rolling and It seemed impossible that they might hit a momentum speed bump before the All-Star break arrived. And, in the spirit of the season, the Celtics were like, “Hold my beer.” First, the Celtics watched Rajon Rondo stun them with his first career buzzer-beater (with Kevin Garnett watching from the front row, no less) while James and the Lakers rallied late in Boston. Two days later, a nametag-wearing Clippers roster rallied from 28 points down to hand Boston a candidate not only for the worst loss of the season but perhaps of the Brad Stevens era. Keeping with the theme of the season, Celtics players decided to pour gasoline on a bad loss when Morris sounded off after the loss. "Guys are hanging their heads. It’s just not fun. It’s not fun,” said Morris. "We’re not competing at a high level. Even though we’re winning, it’s not fun. I don’t see the joy in the game … I mean, it hasn’t been fun for a long time, man.” 

The Celtics pulled themselves together in time to take down Philadelphia’s new-look starting five on the road and hammered home the notion that Boston tends to play to the level of its competition. Even the All-Star Game couldn’t pass without drama and a video circulated showing Irving and good friend Kevin Durant chatting in the hallway before the game. Some online sleuths tried to suggest that Irving and Durant were talking about teaming up in New York next season and Irving would be forced to answer questions about the video when the team reconvened in Milwaukee.

Feb. 21, 2019: At a loss … before the loss
Given an opportunity to downplay the hype around the video from All-Star weekend, Irving gave the story more life by venting that he even had to acknowledge it. "So it’s a video of me and one of my best friends talking, and then it turns out to be a dissection of a free agency meeting? Do you get that? Like, do you get that?” Irving asked reporters. "And then I’m asked questions about it? That’s what disconnects me from all that s---. Like, because I have no connection to that. Over a video? I’m asked a question about the fans, and you brought up the fans. Come on, man. You do it for the likes and clicks. Everybody does. Everybody wants to hear me talk like this. Everybody wants to hear an athlete talk about bulls--- like this. A video though? To pour water on it? It makes no sense. It just makes no sense. It’s not real life.” Compounding matters, Irving misfired at the buzzer and the Celtics lost to the East-leading Bucks in the first game after the break.


Feb. 23, 2019: Bulls on parade
Just when you thought it would be impossible for a game to muscle its way into “worst loss of the season” contention considering the early applicants, the Celtics dug themselves a 25-point hole while falling to a Bulls team they had smothered by 56 earlier in the year. On the positive side: The Celtics didn’t make matters worse by pouring more gas on the loss with their comments and Irving actually pivoted from his typical stance by noting, "I don’t get frustrated by this stuff anymore. It’s just part of the regular season. In the playoffs, when we plan for a team, prepare for a team, I still don’t see anybody beating us in seven games.” Asked why he was confident that Boston’s regular-season woes wouldn’t seep into the playoffs, Irving added, "Because I’m here.”

Feb. 26 + March 3, 2019: Nothing left of their identity
Even after a disastrous February in which their defense eroded and they routinely responded poorly to adversity, the Celtics could still cling to the notion that they played their best basketball against elite competition. Then Boston fell behind by 31 in Toronto and 28 against the Rockets. Irving was tight-lipped after both losses but especially after the Houston defeat.  Most damning might have been when he was asked if he thought the team could come together on the four-game trip it was set to embark on. “We’ll see,” he shrugged.

March 3-March 11, 2019: Soul Plane
In a season full of turbulence, it’s ironic that one of the more turbulence-free moments came during a seven-hour plane ride to San Francisco. The Celtics were reeling after the Houston loss and Irving’s frustration was palpable. But it was Irving who tried to rally the troops at 35,000 feet. Said Al Horford: "Kyrie was instrumental because he was the one that initiated everything as far as being like, ‘Hey, let’s have conversations, let’s play cards, let’s do this, let’s do that' on this plane ride. And we were all engaged at that point.” The Celtics stomped the Warriors — maybe their signature win of the season — then Gordon Hayward hit a buzzer-beater the next night in Sacramento. Sprinkle in a win over the Lakers and Boston could shrug off the fact that they gave up 140 points to the Clippers to prevent a four-game sweep out west. The Celtics returned to Boston with renewed confidence but their issues were still in the cargo hold.


March 24, 2019: Yet another team meeting
All the good vibes from the west coast trip had washed by the end of a four-game losing streak that included falling to Isaiah Thomas and the Nuggets during his long-awaited return to Boston, a gut punch in Philadelphia against the Sixers' new-look starting 5, and a LaMarcus Aldridge butt kicking when the Spurs visited. After the loss to San Antonio, the Celtics huddled — again — for a team meeting. Marcus Smart downplayed the tone of the meeting and noted it mostly involved watching film to see what the team could improve. Pleaded Smart: "We just got to take a deep breath.”

April 7, 2019: Not very Smart
Late March and early April were filled with encouraging moments. The Celtics found success moving Aron Baynes into their starting lineup, Gordon Hayward played with newfound aggression, and Boston’s playoff fate took shape. Even though Boston settled for the No. 4 seed, they locked in a favorable matchup with the Pacers. Alas, in the penultimate game of the regular season — with the team very much planning to rest its stars in the finale — Marcus Smart suffered an torn oblique muscle, taking one of Boston’s most impactful players off the court for the start of the playoffs.

April 30, 2019: Health scare for Ainge
The Celtics ripped off five straight wins to start the playoffs but, before Game 2 in Milwaukee, president of basketball operations Danny Ainge suffered a mild heart attack, his second in nearly 10 years. While Ainge received immediate attention and a full recovery is expected, it was a sobering reminder that there are bigger issues than basketball.

May 8, 2019: What happened to Playoff Kyrie?
After stealing Game 1 in Milwaukee to open an Eastern Conference semifinal series, the Celtics dropped four in a row to the Bucks with Kyrie Irving enduring maybe the worst four-game shooting stretch of his career. The legend of Playoff Kyrie took a hit as Irving improbably struggled to make shots of all varieties. Irving connected on just 19 of 62 shots over the middle three games of the series, then went 6-for-21 (1-for-7 on 3's) in Game 5. Compounding matters, Gordon Hayward went invisible in the series and a lot of Boston's worst regular-season habits resurfaced, essentially ending the Celtics' season.

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