How the Celtics’ Title Window Disappeared: A Timeline

Jun 1, 2021; Brooklyn, New York, USA; Boston Celtics small forward Jayson Tatum (0) reacts during a timeout late during the fourth quarter of game five of the first round of the 2021 NBA Playoffs against the Brooklyn Nets at Barclays Center. Mandatory Credit: Brad Penner-USA TODAY Sports

The 2017 offseason brought two All-Stars to Beantown—Hayward and Irving—but Boston’s luck turned sour less than six minutes into the season. Attempting to catch an alley-oop from Irving, Hayward suffered a gruesome fractured tibia and dislocated ankle in the season-opener against the Cavaliers.

He was out until October 2018 and, though he made an impressive comeback over time, never quite returned to the form he showed as an emerging star on the Utah Jazz. 

In November 2020, with both parties ready to move on, Boston sent Hayward to the Hornets.

While Hayward watched from the sidelines, Irving was amazing in his first season with the Celtics. He was even an early MVP candidate. But he, too, eventually ran into some bad injury luck.

In March 2018, with the playoffs looming, Kyrie underwent surgery on his left knee. It was a procedure he had needed since 2015, but the recovery kept him out until the next season.

Boston finished with the East’s No. 2 seed and, despite lacking its two biggest stars, fought valiantly in the postseason. Jayson Tatum emerged as a star, going toe-to-toe with LeBron James. 

The Cavs outlasted Boston in seven games in the Eastern Conference Finals, but Boston’s future looked bright.

Boston’s unsatisfying era has been marked by several “almost trades” for stars that never actualized. The first: the Celtics’ bid for Kawhi Leonard.

From the time it became unclear Leonard wanted out of San Antonio, Boston was a frontrunner for the 2014 Finals MVP. But Boston’s offers were too stingy.

According to Jay King of The Athletic, the Celtics refused to include any of their young stars in a trade package. Boston had an embarrassment of riches to use as trade chips—Tatum, Brown, Smart, Robert Williams, three 2019 first-round picks, two 2020 first-round picks— but couldn’t get the job done.

“The Celtics never indicated they were willing to put top young players Jayson Tatum or Jaylen Brown into a trade package,” King reported.

San Antonio likely would’ve preferred Tatum or Brown but instead accepted Toronto’s offer: DeMar DeRozan, Jakob Poeltl, and a 2019 first-round pick (with Danny Green also joining Toronto).

Leonard only spent one year in Toronto but led the Raptors to the franchise’s first NBA title.

The “almost trade” saga also includes Anthony Davis...who has also gone on to help lead his new team to a title.

It was no secret that Boston had its eye on Davis for years. But the Celtics never got too aggressive in their pursuit of the New Orleans Pelicans’ star big man, playing it safe as they did with San Antonio.

The Celtics “refused to make Jayson Tatum available in trade talks with New Orleans,” according to Marc Stein of The New York Times. 

Instead, New Orleans sent Davis to the Lakers in July 2019, receiving Lonzo Ball, Josh Hart, Brandon Ingram, and three first-round picks.

When it rains, it pours. After falling to the Milwaukee Bucks, 4-1, in the East semifinals and missing out on Davis, Boston also lost its franchise point guard. 

Boston tried hard to make Irving feel at home, but he never seemed totally comfortable.

Irving signed with the Brooklyn Nets in free agency that summer, following his longtime friend Kevin Durant.

The Nets are loaded, with Irving, Durant, and 2018 MVP James Harden on the same roster. Brooklyn’s star-studded squad just bounced Boston from the first-round of the playoffs.

It was a painful loss for Boston for several reasons. One source of the pain: Boston reportedly was in the mix to acquire Harden when he went on the market last summer.

According to The Athletic’s Sam Amick, the Celtics’ “level of interest and involvement” in Harden “far surpassed” what Ainge indicated to the press. Amick reported Boston was weighing a package that involved sending Jaylen Brown to the Rockets. 

But—as became par for the course for Boston—this potential megadeal never solidified, and the Celtics finished the season .500, claiming the No. 7 seed before a quick postseason exit.

Boston now heads into the 2021 offseason looking for a new head coach and wondering what moves will be needed to get back into the championship picture.