With one week to go until NBA Opening Night, expectations for the Boston Celtics are all over the place, and rightfully so. The Celtics had a tumultuous offseason as Brad Stevens retooled the roster after a disappointing first-round exit. After dominating the NBA for a decade, Stevens made the shocking decision to trade All-NBA forward Jaylen Brown to the Philadelphia 76ers for veteran forward Paul George and draft picks. The Brown trade is partly why the Celtics are one of the biggest wild cards entering the season.

How will the team look without Brown for the first time since 2016-17? Can Paul George or Mitchell Robinson stay healthy? Will Derrick White bounce back from a down year? All those questions and more will need answering. 

Despite the uncertainty surrounding the first year of the post-Brown era in Boston, Yahoo’s Kevin O’Connor is bullish on the Celtics prospects heading into the Oct. 20 opener in Detroit. 

“I’m gonna say the Celtics are going to win more games than they had last year, and they get the East No. 1 seed,” O’Connor said on Monday’s edition of the ‘Kevin O’Connor Show’. 

O’Connor’s “semi-bold” prediction drew immediate pushback from his guest on the show, The Ringer’s Chris Vernon. “That is not semi; that is ridiculous,” he said. 

But O’Connor defended his argument well: “George and Tatum looked legitimately good; there was some synergy between those guys,” he said. “George and Tatum looked like they had more synergy together than Tatum and Brown ever did; it’s stupid to say that, but it just felt like there was a natural flow between those guys, like there was no friction between them,” he continued. 

O’Connor, of course, mentions “friction” between Tatum and Brown, a seemingly never-ending storyline leading up to and since the deal. Did the two stars secretly hold animosity towards each other? Ultimately, we’ll never know the true answer to that question. However, there is something to be said for George being a better complement to Tatum’s game as more of a spot-up shooter than Brown, allowing Tatum to drive to the basket and look for the six-time All-NBA forward on the perimeter. 

O’Connor was met with more pushback from Vernon, who cited a much-improved Eastern Conference as a reason for the Celtics to take a step back. Vernon is right; plenty of teams made major improvements over the offseason. The Miami Heat made a blockbuster trade with the Milwaukee Bucks to land two-time MVP Giannis Antetokounmpo, the Toronto Raptors added former Finals MVP Kawhi Leonard, and Philadelphia added Brown and LeBron James to join Tyrese Maxey and Joel Embiid. 

With the reigning NBA Finals Champion New York Knicks, a 2025-26 breakout team in the Detroit Pistons, and Indiana Pacers star Tyrese Haliburton returning to full health, Vernon is right: the Eastern Conference is much improved. 

However, that discredits the idea that the Celtics may actually be better off without Brown. Despite George's rough shooting night, O’Connor is right: the pair looked like they fit together seamlessly in Saturday’s preseason win over the 76ers. That’s before you even factor in head coach Joe Mazzulla, who has already drawn high praise in a preseason poll of executives done by The Ringer’s Zach Lowe.

Of course, we still need to answer all those questions mentioned earlier, with George’s ability to stay healthy being the most important. But one thing is becoming clear: the 2026-27 Celtics will make a lot of people look really smart and a lot of people look really dumb, regardless of how the season turns out. 

The Celtics continue preparing for the Oct. 20 opener against the Pistons as they host the Charlotte Hornets in the third of four preseason games at TD Garden on Wednesday night. Tip-off is set for 7:30 p.m. ET.