Of all the Jewish people I know, there isn't a single one who is supportive of Israel's policies towards Palestine and Palestinians, let alone comfortable. But no doubt many are. Being Jewish often doesn't have a whole lot to do with Israel, let alone Spurs and Arsenal.
As to the tw*t in the head tweet needing a context - Spurs isn't an Israeli team so the club is unlikely to drape a trophy in colours, winning the cup wasn't the work of Israel's foreign agents but paid professionals, the majority of its supporters aren't Jewish, and the ones who are Jewish may themselves have no connection with Israel. I'd have thought that context is so obvious it doesn't need stating. Indeed, when Liverpool and Tottenham condemned the tweet they found no reason to spell it out.
Of course it would fall under the IHRA definition. Anti-semitism usually does. Try this one - because spurs / fans would put an Israeli flag on it wouldn’t they… ffs. In supporting a British club as British citizens their allegiance is to Israel. That really isn't hard to spot.
Further, Galloway isn't wading in on the British clubs who are supported in Israel, by Israel, and whose flags are flown within Israel - it's highly selective. It's a tweet that would appeal to the ignorant. It's complicated a bit, but not much, by the history of anti-semitic abuse directed towards Spurs in the 70s no doubt and the way that Spurs appropriated symbols from that to demonstrate pride in their fans, and their geography. Presumably that's parallel to the use of the 'N' word in the States, all the way back to the use of the word 'Protestants' in the church. If and when Spurs fans wave Israel flags, it is no doubt because it has the star of David on it to be waved in the face of the 'Y' word. But I've never seen one when I've seen Spurs play and you'd struggle to find a photo of one on google images I imagine, unless it was flown by an Ajax fan vs Spurs.
As to tw*t winning a court case, given the history of that radio station's troubles with the regulators given tw*t's previous comments, I'm sure they'd consulted their lawyers long before his latest round of tw*ttery. He knew exactly what he was doing as I'm sure do many who are posting in a hifi shop about AS.