On paper, the Ryuyukai were the most fearsome team in Japanese softball. A sort of mutual aid society for retired gangsters, the club had racked up nearly a century of hard time. The manager had been a top mob consigliere; the relief pitcher, who took the field in hot pink shoes, had once been sent to kill him.

But on a cloudless day last March, these hardened ex-cons met their match: the Parent-Teacher Association of Nakanodai Elementary School. The P.T.A. showed no mercy, hitting pitch after pitch out of the scruffy park in suburban Tokyo. Midway through the game, the scorekeeper stopped counting.

Losing is nothing new for Japan’s iconic gangsters, the yakuza. For over a decade, they have been suffering one defeat after another.

As late as the 1990s, yakuza numbered around 100,000. Their businesses — scams, gambling and prostitution rackets — were illegal, but the groups themselves were not. Fan magazines chronicled their exploits, sandwiching interviews with top bosses between organizational charts and brothel reviews. The groups had business cards and listed addresses. They gave Halloween candy to children and distributed relief supplies after disasters.

But today’s yakuza are a shell of what they once were. The same demographic forces wearing down other Japanese industries have also hit organized crime. An aging population has made it hard to find young recruits — more Japanese gangsters are in their 70s than in their 20s — and has diminished the once-thriving demand for the yakuza’s services.

Society, too, has become less tolerant of them. The authorities have carried out a relentless legal assault on the criminal underworld. Crime is both less profitable and riskier: In 2021, a court sentenced the head of the most violent syndicate to death, a first that sent shock waves through the mob’s executive class.

All of that has made crime a less attractive career option. Over the last decade, the yakuza’s rolls have plummeted by nearly two-thirds, to 24,000.

Many have struggled to reintegrate. Tattoos, missing fingers and long criminal records limit job opportunities and make it difficult to fit in. Japanese laws discouraging business with the yakuza effectively stop them from taking care of necessities like opening a bank account, getting a phone plan or renting an apartment until they can prove they’ve been out of the yakuza for five years.

Yuji Ryuzaki, the softball team’s manager, established the Ryuyukai in 2012 to help his former colleagues build a new life.