The Biggest Gambles in Celtics History

One could argue that 16 of Boston's 18 championships came from a trade or a draft pick that could have gone very wrong. Some of those moves paid off within a year, and one took more than a decade.

Not every move worked out, and the one Boston made this summer has most fans wishing it never happened. Let’s revisit some of them.

6 Celtics Moves That Could Have Gone Either Way

Every move on this list was a big call that could make or break the franchise. In poker, before you make a call, you can run your hand through a poker odds calculator and see your win percentage. In sports, there's nothing like that, so even a smart trade can feel like a coin flip.

1956: The Trade for Bill Russell

Red Auerbach traded Ed Macauley and Cliff Hagan to St. Louis for the No. 2 pick, with both of them later making the Hall of Fame. That's a big price for a rookie some pro coaches still doubted.

He even missed the first weeks of the season at the Olympics, and still won 11 titles in 13 seasons.

1978: Waiting a Year for Larry Bird

Auerbach took Larry Bird with the sixth pick, even though Bird planned to stay in college one more year. If Boston didn't sign him within a year, he would go back into the draft.

While Boston waited, Bird took Indiana State all the way to the national title game. When he finally signed, it was the richest rookie deal in team sports back then, at $3.25 million over five years. You probably know the rest, with three titles and three straight MVP awards.

1997: Two Lottery Picks, No Duncan

Boston went 15-67 in 1996-97, which is still the worst record in team history. At least the Celtics had two picks in the lottery and a 36% shot at Tim Duncan. No team had better odds, so you can imagine how many fans were picturing him in green.

Sadly, the lottery didn't go Boston's way, and San Antonio won it with only a 21.6% chance. Duncan won five titles with the Spurs and later said, "In my head, I was going to Boston."

2007: KG and Ray Allen Come to Boston

After a 24-58 season, Danny Ainge decided he was done waiting. First, he landed Ray Allen on draft night for the No. 5 pick and two players. A month later, he went even bigger, sending Al Jefferson, four other players, and two first-round picks to Minnesota for KG.

Honestly, that's a lot for two guys over 30, but Boston won title No. 17 right away.

2013: Pierce and KG Head to Brooklyn

By 2013, Pierce was 35 and Garnett was 37, so Ainge traded them to Brooklyn while they still had some value. The Nets also took Jason Terry and gave up five players, three unprotected first-round picks, and a pick swap.

It was strange to see those two in Nets jerseys. They won just one playoff series, and by 2015, Pierce was in Washington and KG was back in Minnesota.

Boston used those picks to get Jaylen Brown and Jayson Tatum, who won the 2024 title together.

2026: Jaylen Brown Goes to Philadelphia

Last but not least, this summer Brad Stevens traded the 2024 Finals MVP to Philadelphia, two months after the Sixers knocked Boston out. Boston got Paul George, who is 36, and four draft picks back.

Stevens said it came down to money, since Tatum and Brown were taking up 70% of the salary cap. Funny enough, Brown came from that Brooklyn trade, so the 2013 deal is still paying off.

Worth the Risk?

Most of these moves worked out, since four of the six ended with a championship. The Duncan lottery is the only one that didn't, and the Brown trade needs a few years before anyone can draw a conclusion.

Brown didn't leave on bad terms, with a farewell party on Boston Common and the key to the city. Fans will get their chance to react on January 21, when he plays his first regular-season game back at TD Garden.