The 10 Best Offseason Moves in Boston Celtics History

As one of the original Basketball Association of America teams, the Boston Celtics pre-date the NBA. When a team has been around for that long and won as many titles as they have, there are a lot of moves that helped the Celtics hang as many banners as they did.

The word “moves” is intentionally chosen here, because these aren’t all trades. With that in mind, let’s get on with the show.

10. Ainge Steps down

Danny Ainge, Brad Stevens, Wyc Grousbeck — Jul 5, 2013; Waltham, MA, USA; General Manager Danny Ainge talks about hiring new Boston Celtics head coach Brad Stevens, center, as owner Wyc Grousbeck, right, listens in during a news conference announcing Stevens new position. Mandatory Credit: Winslow Townson-USA TODAY Sports | IMAGN IMAGES via Reuters Connect

The move: Danny Ainge announces retirement in June 2021, Brad Stevens takes over as President of Basketball Operations.

Despite it being under-discussed, this is a critical move in modern Celtics history.

Ainge is a Hall of Fame-level executive who has built a lot of the greatness Celtics fans have enjoyed over the years. However, by 2021, Ainge had built a reputation of a guy who “almost” made a lot of big deals, but actually did none.

Part of that reputation was because Ainge stubbornly wanted to dominate every trade. If it wasn’t a fleecing, Ainge didn't want to do it.

Enter Stevens.

Stevens brought a renewed energy to the job, and a willingness to give something up in order to get something back (as you’ll see further down the list). I don’t think Ainge would have made the two moves Stevens did, mostly because they cost Boston some draft capital and important players. Stevens’ willingness to move on in those situations won Boston a championship, which makes this a move worthy of making this list.

In addition to the offseason moves on this list, the Derrick White trade at the 2022 trade deadline is another huge win that helped build a champion. Stevens was panned at the time for giving up two first-rounders for White (one of them is a swap), but he took a risk that Ainge probably would not have.

9. Completing a Dynasty

The move: Rick Robey, two 2nd-round picks to Phoenix for Dennis Johnson, a 1st-round pick, and a 3rd-round pick.

DJ had worn out his welcome in Seattle and Phoenix, but Boston’s blue collar ethos and Larry Bird’s aura made Johnson a perfect fit in Boston. He was already a champion and an All-Star when he got to Boston, and with Bird, Robert Parish, and Kevin McHale, he provided a steady hand to make sure all the big dogs got fed.

Bird has called Johnson his favorite teammate for a reason. DJ was a no-nonsense guy who was all about winning. It was fitting that the back half “and there's a steal by Bird” is “underneath to DJ and he lays it in.”

One of my favorite flashbulb moments in Celtics history is Johnson calling Bird over for that hug after that play.

8. A Huge Pivot

The move: Kevin Garnett, Paul Pierce, Jason Terry, DJ White to Brooklyn for Keith Bogans, MarShon Brooks, Kris Humphries, Kris Joseph, Gerald Wallace, three unprotected 1st-round picks and a pick swap.

When we talk about Ainge’s fleecings, this is right there at the top of the list.

The Nets were trying to make a huge splash under owner Mikhail Prokhorov, and they threw caution to the wind when it came to acquiring Pierce and Garnett. They were just coming off a first-round loss after a 49-win season, and saw the two aging Celtics as veteran pieces to push the Nets to the top.

Wyc Grousbeck’s version of the story is pushing Ainge to keep going for unprotected picks, two of which ultimately led to Jaylen Brown and Jayson Tatum. The Nets, meanwhile, slipped further down the standings and have never gotten past the second round after the trade.

7. Building the 2024 Champs

Jrue Holiday, Kristaps Porzingis — Jan 13, 2024; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) and center Kristaps Porzingis (8) and Houston Rockets center Alperen Sengun (28) battle for a rebound during the first half at TD Garden. Mandatory Credit: Bob DeChiara-USA TODAY Sports | USA TODAY Sports via Reuters Connect

The moves: Stevens’ 2023 Offseason trades. Kristaps Porzingis to Boston in three-team deal involving Marcus Smart, Danilo Gallinari, Mike Muscala, and Julian Phillips.

Malcolm Brogdon, Robert Williams, 2024 1st round pick to Portland for Jrue Holiday.

What? Someone compiling an offseason list taking a liberty with a premise he created? No way!

Yes, I’m lumping both trades Stevens made into one move, even though they came at very different times. The reason is that this isn’t the Ray Allen/Kevin Garnett situation, which I think needs two separate stories.

Stevens saw the impending second apron system (which team owner Wyc Grousbeck helped create) and launched into a series of win-now moves that ultimately built the 2024 NBA champions.

He moved Marcus Smart and Robert Williams, two favorites in Boston, rolling the dice on Porzingis and jumping at the chance to snag Holiday after the Milwaukee Bucks traded him for Damian Lillard.

If I had to separate these moves, I’d rank the Holiday move higher because there were some fit questions after the Porzingis acquisition. The Holiday move was critical for Boston because not only did it snap the roster more into place, Holiday became the adult in the room to settle Boston down during playoff blips that could have extended a series or two.

6. Draft Night Fleecing

The move: 1st overall pick in 2017 draft to Philadelphia for 3rd overall pick (Jayson Tatum selected) and 1st-round pick in 2019

Ainge got a huge assist from the Lakers in this deal.

The whole world though Markelle Fultz was the obvious top pick, but the Celtics had Tatum targeted the whole time. The Sixers wanted Fultz in a big way, so Ainge decided to use that against the Sixers by convincing the world he was taking Fultz first.

Philadelphia gave up their pick and Sacramento’s first-rounder in 2019 to swap places. Tatum became a perennial first-team All-NBA player, while Fultz ruined his jump shot and his career.

This could have been much higher on the list if the Kings didn’t have a shockingly good 39-win season and drop their pick down to 14th.

5. Luring KG to Boston

The move: Jeff Green, Wally Szczerbiak, Delonte West and a 2008 2nd-round draft pick to Seattle for Ray Allen and Glen Davis.

This differs from the 2023 offseason because the next move doesn’t happen without this move.

The Celtics were awful in 2007, dropping to 24 wins and the second-worst record in the league. Ohio State’s Greg Oden was all the rage but Kevin Durant wowed in Texas and won Ainge’s heart.

The Celtics were in a position to get their next generational talent to pair with Paul Pierce, and then …

… they got the fifth pick.

Ainge pivoted, called up Sam Presti in Seattle (who drafted Durant second overall), and swung a trade to send Jeff Green there in a deal for Ray Allen and second-round pick Glen Davis. Allen no longer fit their timeline, so the move made sense for both teams.

Once Allen was on board, Garnett’s attention was piqued, and Boston became a suitable destination for him. Now, Ainge and former teammate Kevin McHale could start talking about Garnett in a way they couldn't before.

4. Stealing Larry Bird

The move: Red Auerbach drafts Bird in 1978 despite Bird going back to school for his senior year, risking losing him.

Bird originally committed to Indiana University, but left and sat out his freshman year. That decision allowed Bird to be eligible for the 1978 draft despite his declaration that he was going back for his senior season.

Auerbach didn’t want to take any chances. He took Bird sixth overall in the 1978 draft and risked losing him if they couldn't negotiate a deal prior to the 1979 draft.

Bird went back to school, won nine different player of the year awards, and played hardball with Auerbach’s low-ball offers. Ultimately, the Celtics gave Bird a five-year, $3.25 million deal weeks before that next draft, making him the highest-paid rookie at the time.

All Bird did after that was win Rookie of the Year, three MVP’s (consecutively), three championships, and two Finals MVPs to be widely considered among the top NBA players of all time.

3. The New Big 3

The move: Al Jefferson, Ryan Gomes, Gerald Green, Theo Ratliff, Sebastian Telfair, two 1st-round draft picks in 2009 NBA draft to Minnesota for Kevin Garnett

With Ray Allen in the mix, Garnett was suddenly open to a future in Boston. At the time, Jefferson was a promising young big man coming off a season where he averaged 16 points and 11 rebounds. He might go down as the last true NBA post player, but it’s a skill that the NBA was moving away from.

Maybe the post play was why McHale was so willing to take Jefferson in the deal. There were some arguments in Boston that the Celtics were giving up a lot in the deal considering how well Jefferson was progressing, but Ainge pulled the trigger and built a new Big 3.

Jefferson averaged 20 points and 10.4 rebounds in three years as a Timberwolf, but Garnett changed the entire culture of the Celtics, leading the biggest turnaround in NBA history at the time and the 2008 NBA championship.

2. The Original Big 3

The move: 1st and 13th overall picks in 1980 NBA draft to Golden State for Robert Parish and the 3rd overall pick (Kevin McHale selected)

These next two moves are in permanent ink at the top of everyone’s top-whatever trades lists.

Parish spent four years in Golden State, but he and the team weren’t really going anywhere, so the Warriors decided to pivot. They saw Joe Barry Carroll as the answer to their problems.

The Celtics had the top pick in that draft and Larry Bird on the roster. They saw the opportunity to build a great frontcourt around their young star, and they didn’t value Carroll the same way the Warriors did.

The result was one of the most lopsided deals in NBA history. Boston drafted McHale with the third pick and created the Big 3, which dominated the mid-80’s NBA. Parish and McHale will be remembered as two of the 50 greatest NBA players of all time, and Carroll will be remembered for having the nickname “Joe Barely Cares.”

1. The Greatest Winner Ever

The move: Ed Macauley, Cliff Hagan to St. Louis (and the Ice Capades to Rochester) for second overall pick in 1956 (Bill Russell selected)

Bill Russell might be the single greatest winner in the history of sports. He won two national championships at San Francisco, Olympic gold, and 11 NBA championships with the Boston Celtics.

But he existed in a unique era in NBA (and American) history. The league was still very much in its infancy, and there was no guarantee it could survive. At the same time, the league was only just beginning to integrate, and racism was stronger than championship aspirations among some teams.

So was the need to make money, and the NBA wasn’t a huge draw at the time.

Red Auerbach and Celtics owner Walter Brown didn’t care about bringing a Black star to Boston, and the opportunity to get Russell was too good to pass up. So they put the most incredible plan in place.

The Rochester Royals had the first pick in the draft, but they were looking for a guard. Brown, who owned the money-making Ice Capades at the time, made sure the Royals kept looking for a guard by promising them the ice skating show booking for passing on Russell.

The St. Louis Hawks were second, and they coveted hometown star Ed Macauley. The Celtics threw in Cliff Hagan and the second pick, and Russell, came to Boston.

What people don’t remember is that the trade actually worked out, to some degree, for both sides. The Hawks actually went to the Finals (losing to Boston) the season following the trade, and then won the championship the year after that. It just happened to be the only championship in team history.

Russell led the Celtics to 11 rings, including eight in a row.

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