The Detroit Pistons had not won an NBA game in a very, very, very long time entering play Saturday against the Toronto Raptors. So long, in fact, that the Pistons — who were supposed to be on the rise this season — were just one loss away from breaking the one NBA record that no team wants to call their own… the longest losing streak in NBA history. They just recently became the first team to lose 27 games in a row in a single season and then lost a 28th straight game in heartbreaking fashion, blowing a 21-point lead against the mighty Boston Celtics and losing in overtime.

But instead of becoming the first NBA team to ever lose 29 straight games, the Pistons emerged victorious against the Raptors, who had just traded OG Anunoby to the New York Knicks earlier in the day. So, Detroit ends this losing streak tied with the Philadelphia 76ers for the longest losing streak ever. Let's take a look at the biggest losers in NBA history.

5th: 1981-82/1982-83 Cleveland Cavaliers

Losing Streak: 24 games

First Loss: March 19th, 1982 vs. Milwaukee Bucks

Double-Digit Losses: 12 games

Win to Break the Streak: November 10th, 1982 vs. Golden State Warriors

This 24-game losing streak that spanned two seasons coincides with an historically horrible stretch of Cleveland Cavaliers basketball that is best known for the creation of the Ted Stepien Rule. Here's the CliffsNotes version of the Stepien era: Ted Stepien bought the Cavaliers in 1980 and threw draft picks away with such little regard for pennies on the dollar that after Stepien sold the Cavaliers to Gordon Gund in 1983, the NBA had to step in and allow Gund to pay for 1st round picks each year since Stepien had traded them all away. From there, the NBA made a rule — the Ted Stepien Rule — that teams could not trade away 1st round draft picks in back-to-back years.

If it weren't for Art Modell, there's a very real chance that Ted Stepien would be the most hated man in Cleveland sports history. Fans hated him and routinely heckled him at games, and you can't really blame them. You know who the four players who started the most games for the Cleveland Cavaliers were in the 1981-82 season? Of course you don't, because you're not a psychopath. Are you familiar with the skillsets of James Edwards, Geoff Huston, Kenny Carr, and Ron Brewer? Of course you're not, because again, you're not a psychopath.

My favorite nugget from the Stepien era in Cleveland: the Cavaliers had five different head coaches in three years. Incredible.

2nd (tied): 2013-14 Philadelphia 76ers 

Losing Streak: 26 games

First Loss: January 31st, 2014 vs. Atlanta Hawks

Double-Digit Losses: 19 games

Win to Break the Streak: March 29th, 2014 vs. Detroit Pistons

Even though this isn't the record-holder for the longest losing streak in NBA history, the 76ers 26 game losing streak in 2014 may be the worst stretch of ineptitude we've ever seen in the NBA. This was the start of the “Trust the Process” era in Philadelphia, and even though Joel Embiid was the draft prize the Sixers received after going 6-35 in the second half of the 2013-14 NBA season, the Sixers blatant lack of interest in winning basketball games became a major story around the NBA, and it would continue into the next couple of seasons following this one.

Look at the box scores from this 26 game run, and you'll notice a whole lot of Tony Wroten, Henry Sims, Spencer Hawes, James Anderson, and Byron Mullens in there. That might not have been a recipe for winning in the NBA in 1954, let alone 2014. The 76ers were outscored by an average score of 111.3-94.3 during an era when the league scoring average was 101 points. That means the Sixers were scoring seven points fewer and giving up ten points more than the league average for a 26 game stretch of the season.

76ers fans were told to Trust the Process

2nd (tied): 2010-11 Cleveland Cavaliers

Losing Streak: 26 games

First Loss: December 20th, 2010 vs. Utah Jazz

Double-Digit Losses: 14 games

Win to Break the Streak: February 11th, 2011 vs. Los Angeles Clippers

The Cleveland Cavaliers went from back-to-back 60+ win seasons in 2008-09 and 2009-10 to what was at the time the longest losing streak in NBA history. I'm pretty sure you know why things went down the way they did, but if you don't, here's a hint.

1st: 2014-15/2015-16 Philadelphia 76ers

Losing Streak: 28 games

First Loss: March 27th, 2015 vs. Los Angeles Clippers

Double-Digit Losses: 12 games

Win to Break the Streak: December 1st, 2015 vs. Los Angeles Lakers

In this two season stretch, the Sixers went a combined 28-136. Combine that with the 6-35 record Philadelphia had in the 2nd half of the 2013-14 season, and we're looking at a two and a half year run where the 76ers won just 34 of 171 professional basketball games, and had losing streaks of 26 and 28 games. I'm fairly confident we'll never see something like that again, and the only reason I won't go as far as saying I'm 100 percent sure is because of what's happening with the Pistons right now.

I thought that in this age of the NBA, with load management and three-pointer variance seemingly evening the playing field across the league, it would be unlikely that we would see losing streaks or winning streaks that threaten the all-time records. Now, I'm not so sure. See, while the Pistons don't yet seem to be “tanking” in the traditional sense, that's all the Philadelphia 76ers were doing up until the 2016-17 season. Not only were the 76ers tanking, but general manager Sam Hinkie was completely unapologetic about it. It was a well-conceived plan to give the Sixers as many bites at the metaphorical apple as possible, only it threatened the competitive standing of the league to have a team so flagrant in their attempts to tank games.

Well what does it say about the health of the league when a young and seemingly talented team — at least on paper — like the Pistons are trying to win games and can't?

1st (tied) 2023-24 Detroit Pistons

Losing Streak: 28 games

First Loss: October 30th, 2023 vs. Oklahoma City Thunder

Double-Digit Losses: 14 games

Win to Break the Streak: December 30th, 2023 vs. Toronto Raptors

Detroit Pistons fans suffered through Halloween, Veterans Day, Thanksgiving, Black Friday, all eight crazy nights of Hanukkah, and Christmas without watching their team secure a win. The holiday season is supposed to be a joyous time, and yet, the Pistons threw lumps of coal at the heads of their fans on a nightly basis.

The losing streak fell just short of 2024, though, with the Pistons beating the Raptors just days before the calendar flipped. The victory brought a sense of relief after so many close calls leading up to it.

Detroit recently had a great shot to end the misery against a short-handed Utah Jazz team that hasn't exactly been lighting the NBA on fire this season either. With the Jazz missing Jordan Clarkson, Lauri Markkanen, Keyontae George, and Talen Horton-Tucker, this represented the best shot yet the Pistons had at putting an end to this losing streak. Instead, the result was another embarrassing defeat.

Detroit followed this up with an 11-point loss to the Brooklyn Nets to tie the single-season losing streak record. The Pistons then held a lead in the fourth quarter against the same Nets, only to melt down despite Cade Cunningham's best efforts.

Detroit went to Boston next to take on a dominant Celtics team and almost shocked the world. The Pistons led by as many as 21 points in the first half and held a 19-point halftime lead, only to give it all away in the third quarter. The game wound up going to overtime, but the end result was the same: a 28th straight loss to tie the all-time record.

But, now, this streak is mercifully over.