The writing was on the wall for Nazareth long before their 7-0 capitulation to Hapoel Ramat Gan on a remarkable last day of the Israeli season. Relegation was assured a week before, but the signs had not looked good for a while.
Teetering on bankruptcy, losing heavily every week on the pitch whilst enduring the racism that follows clubs like Bnei Sakhnin, who proudly claim an Israeli-Arab identity, it had been a miserable season.
But there was one shining light, one that has enthralled fans, not to mention the media: the tongue-in-cheek stoicism of their English manager.
Gregory used to be a contender. After taking Aston Villa to the top of the Premier League, he was tipped as a potential England boss. But bad luck, bust-ups with various chairmen and, ultimately, poor results saw him sacked from successive jobs. When he left QPR in 2007 he disappeared from football. Many thought that would be the last we would see of him.
But last December he stepped out of the wilderness in unconventional style, taking charge of Nazareth, who were rooted to the bottom of the Ligat Ha'al. It was an unconventional move to say the least.
"I have a connection with Najwan Ghrayib [who he signed for Villa in 1999] who is a coach here. I was on holiday and they offered me a contract," he said.
"They are a third or fourth division club playing in the Israeli Premier League. People were saying it was a bad career move, but the more people said that, the more I wanted to come. I'm an Englishman. We love the underdog. Money wasn't an issue. If you're a singer you need to sing, doesn't matter who your audience is. I need to get on the coaching pitch and get my fix."
Nazareth is a modest outfit, even by Israeli standards. They came into a newly expanded Israeli Premier League along with five other teams. But the club from the Galilee, which has a mixed team of Jews and Arabs, only attracts a few thousand home fans. Money has been so tight many of the players were not paid for over two months, not exactly ideal preparation for a relegation dogfight.
"They come off the training pitch and you have no wages to give them, they have no money for food, to pay the rent, food for kids. Players had electricity cut off. I was getting calls from players saying that they didn't have petrol to get to the game," he said. "I was almost acting as a psychologist and CEO. "
Then there's the political situation. Israeli football remains a hotbed of political antagonisms. Travelling teams with supporters singing songs in Arabic do not get a friendly reception from the famously fiery nationalistic support.
When Sakhnin or Nazareth play in Jerusalem they are met by a police escort. But Gregory soon discovered that the fiercest rivalry was with Bnei Sakhnin.
"They don't get on at all, it's worse than when we play Beitar," he laughed. "When we played at Sakhnin the fans had stones and boulders, there were rockets going off. We had to be smuggled out of the town."
Gregory has won plaudits for masterminding some impressive results, including victory over Maccabi Tel Aviv. It was a miracle that Nazareth kept their chance of avoiding relegation alive until the penultimate game of the season .
"He is completely different to any other manager here," one Israeli pundit said. "Football managers in Israel wear scruffy T-shirts and jeans, but Gregory wears training tops and looks like a coach. In interviews, he even talks in English football clichés. But he comes across very well on TV and knows what he's doing."
Gregory certainly didn't appear to be feeling the strain, giving affable interviews to anyone that wanted them. Keeping Nazareth up, he said, would have been the "biggest achievement of my life".
His move to Ashdod came as something of a surprise as he was strongly linked with former champions Betar Jerusalem. After signing a three-year contract with Ashdod, Gregory said: "I am certain that I have reached the best place in Israel and I wish to steer Ashdod to new heights in Israeli football."
Only time will tell.