The Detroit Pistons find themselves at a crucial juncture in their season as they prepare to face off against the Toronto Raptors on Saturday. If the Pistons suffer another loss, they will equal the longest losing streak in major American professional sports history, matching the record set by the Chicago Cardinals in the NFL between 1942 and 1945.

The Pistons have already endured an abysmal season, setting an unparalleled single-season of NBA failure with 28 consecutive losses. Their latest defeat came in a heartbreaking overtime loss to the Boston Celtics, where they let a commanding 19-point halftime lead slip away in the third quarter, falling 128-122.

Head coach Monty Williams expressed sympathy for his team, recognizing their efforts to break the losing streak. "I hurt for them, you know we feel like we're just getting so close to not just winning one game but winning a lot of games if we play that way versus most teams in the league," Williams shared with reporters. He commended the team's character and integrity in the face of adversity.

Desperate to rebuild through youth, the Pistons have invested in high draft picks in recent seasons, including Cade Cunningham, the No. 1 overall pick in 2021, and Ausar Thompson, the No. 5 pick this year. They also secured the services of Coach Williams with a substantial coaching contract. However, rather than exhibiting glimpses of future success, this Pistons team has sadly joined the league's worst-ever NBA teams.

The Pistons' win-loss record of 0.065 this season is worse than the 1972-1973 Philadelphia 76ers, the 2011-12 Charlotte Bobcats, the 2015-16 Sixers, and the 1992-93 Dallas Mavericks, who all had their share of struggles. The '72-'73 Sixers still hold the dubious distinction of the worst-ever NBA season with a 0.110 winning percentage.

With an average age of just 23.5 years, the Pistons boast the youngest roster in the league, and their lack of experience is evident in their depressing losing streak. Former Pistons star and current NBA head of basketball operations, Joe Dumars, empathized with the team's plight, particularly given his connection to the organization. "It's tough to watch the guys go through that... I hope they can end the slide sometime soon," Dumars expressed to The Athletic.

The Pistons will tip off against the Toronto Raptors at 6 p.m. ET on Saturday, with both teams aware of the stakes. The Pistons will need to summon every ounce of determination to avoid tying the Cardinals' infamous record and salvage their season. As fans and basketball enthusiasts watch nervously, all eyes will be on the Pistons in this pivotal matchup.