The Worst Draft And Trade Mistakes In Boston Celtics History

The Boston Celtics are widely recognized as one of the most successful franchises in NBA history with 17 NBA championships, the most in NBA history, as their biggest piece of evidence. While it takes a special and beyond-intelligent organization to achieve such things in the NBA, mistakes have been made along the way, whether through the draft or via trade over time. No NBA team is perfect and the Boston Celtics are no exception. 

The Worst Draft Mistakes In Boston Celtics History

1958 NBA Draft

Boston Celtics Selected: Bennie Swain, 8th Overall Pick

Better Available Pick: Hal Greer (14th Overall Pick)

Heading into the 1958-59 season, it was quite clear that the Boston Celtics were all set at the guard position with Bob Cousy and Sam Jones making up their backcourt. For this reason, they decided to go with 6’8’’ power forward Bennie Swain out of Texas Southern. Unfortunately for Boston, Swain would play just one season in the NBA before calling it quits, averaging 4.6 points and 4.5 rebounds per game. Hey, at least he ended it on a high note as the Celtics began their streak of eight straight NBA titles that same season.

Although their backcourt was already solidified with Cousy and Jones, one cannot help but wonder what could have been had the Celtics selected guard Hal Greer who dropped to 14th to the Syracuse Nationals. Greer went on to have a Hall of Famer career with the organization, earning 10 All-Star selections, seven All-NBA Team selections, and an NBA championship in 1967. If Boston had decided to go with Cousy and Greer in their backcourt while sliding Jones to small forward, the Celtics dynasty could have lasted much longer than it did.

1975 NBA Draft

Boston Celtics Selected: Tom Boswell, 17th Overall Pick

Better Available Pick: Gus Williams (20th Overall Pick)

It would be nearly two decades before the Celtics swung and missed terribly in the NBA Draft. With their first-round selection in 1975, the Celtics decided on 6’9’’ power forward Tom Boswell from the University of South Carolina. Boswell struggled to crack the Celtics rotation during his rookie season, playing in just 35 games for less than 8.0 minutes per game as the team went on to win the 1976 NBA title. Boswell would play two more seasons in Boston averaging 5.9 points and 3.9 rebounds per game.

Boswell would go on to play 97 games in Denver and 61 games in Utah before deciding to go overseas to play in Italy in 1981. He did return to the Jazz briefly in 1983-84 for 38 games and averaged just 1.9 points per game

Just three picks after Boswell went to the Celtics, future NBA champion and All-Star Gus Williams was drafted by the Golden State Warriors. Williams would be decent with the Warriors but is well-known for his days with the Seattle SuperSonics where he was a two-time All-Star and an NBA champion in 1979. In six seasons with the SuperSonics, Williams averaged 20.3 points, 6.0 assists, and 2.3 steals per game. His addition to the Celtics of the 1980s would have added even more firepower to their rivalry with the Lakers during the decade.

1976 NBA Draft

Boston Celtics Selected: Norm Cook, 16th Overall Pick

Better Available Pick: Alex English (23rd Overall Pick)

Even after winning the NBA championship in 1976, the Boston Celtics had the chance to add elite offensive players once again in that summer’s draft. With their 16th overall selection, the Celtics decided on Norm Cook, a small forward from the University of Kansas. Cook would go on to play a total of 27 games in the NBA between 1977 and 1978 with the Celtics and Nuggets, averaging 2.4 points and 1.1 rebounds per game. He hung up his shoes for good following the 1978 season.

Just a few picks down the board, Alex English was taken by the Milwaukee Bucks with their 23rd pick. However, even Milwaukee didn’t see the full potential of English and traded him just two seasons into his career. It would not be until he arrived with the Denver Nuggets in 1980 that he would evolve into one of the game’s most dangerous scorers. From 1982 through 1989, English poured in eight straight 2,000-point seasons with a scoring title and eight All-Star appearances to go along with them.

While he never was able to capture an NBA championship, English made the Nuggets one of the most dangerous offensive teams in NBA history as he averaged 25.9 points per game on 50.9% shooting in 11 total seasons with the franchise.

1989 NBA Draft

Boston Celtics Selected: Michael Smith, 13th Overall Pick

Better Available Pick: Tim Hardaway Sr. (14th Overall Pick)

It would be another decade before the Celtics made their next costly draft mistake. In 1989, following having to watch their rival win another NBA championship, the Celtics decided to go big once more with power forward Michael Smith from BYU at 13th in the NBA Draft. It turns out that Smith would be a mid-first-round bust, playing just 112 games in two seasons with Boston, averaging 4.9 points per game in just 9.0 minutes of action.

After he was done in Boston, Smith would go on to play overseas in Italy and Spain before returning for 29 games with the Clippers during the 1994-95 season.

Just one selection after Smith was taken, the Golden State Warriors took point guard Tim Hardaway with their 14th overall pick. Now, the Celtics already had Dennis Johnson, who was 35 at the time, and three backup point guards. Unfortunately, they missed an opportunity to help groom Hardaway for the future at point guard, a position they would struggle to fill during the rest of the 1990s. Hardaway would become a Hall of Famer with five All-Star selections and five All-NBA Team selections in 14 seasons with the Warriors, Heat, Mavericks, Nuggets, and Pacers.

2020 NBA Draft

Boston Celtics Selected: Aaron Nesmith, 14th Overall Pick

Better Available Pick: Tyrese Maxey (21st Overall Pick)

As is well-documented, the Boston Celtics have done a tremendous job over the last 30 years with their scouting and draft capital. In 2020, however, Boston missed an opportunity to add one of the game’s top young point guards in 2023-24, and they didn’t even know it.

With the 14th pick in the 2020 draft, the Celtics decided on 6’5’’ small forward out of Vanderbilt, Aaron Nesmith. Originally seen as a big part of their plans, Nesmith struggled in a bench role with the team in his first two seasons. In 98 appearances, Nesmith averaged just 4.2 points and 2.2 rebounds per game. Nesmith would be dealt during the 2022 offseason for Malcolm Brogdon. Since arriving in Indiana, Nesmith has settled into a bigger role and is performing well with 11.0 points and 3.8 rebounds per game in 129 games including 91 starts.

The Worst Trade Mistakes In Boston Celtics History

1998 Trade Between The Boston Celtics And The Toronto Raptors

Boston Celtics Receive: Kenny Anderson, Popeye Jones, Zan Tabak

Toronto Raptors Receive: Chauncey Billups, Dee Brown, Roy Rogers, John Thomas

The Celtics’ track record as far as trades go has always been very good. Much like every other franchise, mistakes have been made more than once though with their first coming in 1998. In this deal, the centerpiece was Kenny Anderson, the talented point guard who would go on to have some great seasons in Boston, averaging 11.3 points, 5.2 assists, and 1.6 steals per game in five-plus seasons with the team.

Unfortunately for Boston, the other centerpiece would be Chauncey Billups, their third overall pick in the 1997 NBA Draft. Billups would take some time to figure things out but by the time he did, he was one of the most clutch performers in the NBA who went on to become an NBA champion and Finals MVP in 2004 with Detroit as well as a five-time All-Star, three-time All-NBA Team selection, and a two-time All-Defensive Team selection.

For Boston, their point guard for the future was right under their noses the entire time.

2002 Trade Between The Boston Celtics And The Phoenix Suns

Boston Celtics Receive: Tony Delk, Rodney Rogers

Phoenix Suns Receive: Joe Johnson, Randy Brown, Milt Palacio, 2002 First-Round Pick

In 2002, the Celtics would once again make one of the biggest mistakes in team history by trading a rookie without giving him the proper time to prove himself. This time, it would be their 10th overall pick from 2001, Joe Johnson, who would be on the receiving end of the trade news being sent to Phoenix in exchange for Tiny Delk and Rodney Rogers.

While other salary fillers and draft compensation were included, Johnson turned out to be the lone star of this deal. Over the next 18 seasons, Johnson became one of the most lethal offensive players in the game and an incredible performer in clutch situations. Johnson would be a seven-time All-Star and one-time All-NBA Team selection in his career who peaked as a 25.0 points per game scorer in 2007.

Once again, the Celtics being trigger-happy prevented them from being home to one of the league’s brightest young stars.

2003 Trade Between The Boston Celtics And The Dallas Mavericks

Boston Celtics Receive: Raef LaFrentz, Chris Mills, Jiri Welsch, 2004 First-Round Pick

Dallas Mavericks Receive: Antoine Walker, Tony Delk

After being drafted by the Celtics sixth overall in 1996, Antoine Walker went on to star for the franchise for the next eight seasons with three All-Star selections while averaging 20.6 points, 8.7 rebounds, 4.1 assists, and 1.5 steals per game. After the 2003 season, Boston decided to part ways with Walker, welcoming in another large contract and one of the worst mistakes in franchise history.

Boston sent Walker to Dallas along with Tony Delk in exchange for Raef LaFrentz who was only in year two of a seven-year, $70 million deal he signed with Dallas. Walker remained productive in the NBA for five more seasons, even capturing an NBA title in Miami in 2006. LaFrentz would play just three seasons in Boston, averaging 9.2 points and 5.8 rebounds per game as their primary starting power forward.

2011 Trade Between The Boston Celtics And The Oklahoma City Thunder

Boston Celtics Receive: Jeff Green, Nenad Krstic, 2012 First-Round Pick, 2013 Second-Round Pick, Cash

Oklahoma City Thunder Receive: Kendrick Perkins, Nate Robinson

At first glance, this trade doesn’t seem like a big deal but as the after-effects of the trade began to unfold in real time, it turned out it was a game-changer for Boston, and not in a good way. Big man Kendrick Perkins made his NBA debut with the Celtics in 2003 following his selection in the first round of the 2003 NBA Draft.

From there, Perkins’ tenacity and physicality as a rebounder and defender aided Boston in their capture of the 2008 NBA title as well as deep playoff runs thereafter. Despite his contributions, Perkins would be inexplicably traded to the Thunder during the 2011-12 season while struggling with injuries. Funny enough, Perkins and the Thunder would advance to the NBA Finals that season but fall to the Miami Heat.

Meanwhile, the Boston Celtics and their lack of depth on the interior would prove to be their Achilles Heel against the Heat in the second round of the NBA playoffs in 2011-12. Trading away their depth for 9.8 points per game from Jeff Green was not their best moment.

2013 Trade Between The Boston Celtics And The Dallas Mavericks

Boston Celtics Received: Kelly Olynyk

Dallas Mavericks Received: Lucas Nogueira, 2014 Second-Round Pick, 2014 Second-Round Pick

The next and final trade mistake in Celtics history is one that still haunts them to this day. During the 2013 NBA Draft, the Celtics were desperate for a big man, eyeing Gonzaga standout Kelly Olynyk with their 16th pick. However, since Dallas decided to take Olynyk at 13, the Celtics settled for sending their 16th pick, Lucas Nogueira, and two second-round picks to Dallas for Olynyk instead.

It seemed it all worked out for both sides with one minor detail being left out. That detail is that with the 15th pick in that same draft, the Milwaukee Bucks selected Giannis Antetokounmpo, a two-time MVP, NBA champion, and Finals MVP. This means that instead of flipping players with Dallas, Boston could have just taken Giannis by swapping picks with Dallas and adding in the two second-round picks as well, giving Boston full control of the 13th pick and the chance to select Giannis. This would have formed a Big 3 of Giannis Antetokounmpo, Jayson Tatum, and Jalen Brown who would likely have multiple championships by now. It makes this blunder one of Boston’s worst trade and worst draft mistakes in franchise history by far. 

Oh, what could have been.