Given Sheldon's personal affiliations - he is a Labour Party member, a passionate Remainer who still feels like Brexit has been "a kick in the stomach", an active member of New North London Synagogue who has represented Masorti on a number of inter-communal committees, including the JLC, and for the last two years has chaired human rights organisation New Israel Fund UK - his record of defending the "establishment" is perhaps surprising. After all, he takes pride in Masorti being the smallest movement in the British Jewish community "but we punch well above our weight"; his soft spot for the underdog is clear.
"There have been lots of cases I've worked on that have made me uncomfortable," he admits, pointing out that he also specialises in employment law, and represents "both sides" in disputes involving public bodies. "I get more job satisfaction representing the little person, but I believe everyone has the right to representation. It's not for me to decide who's right or wrong - it's for me to present the arguments and a judge to decide."
Sheldon is tight-lipped as to his view on the junior doctors' contract, but admits the case was fascinating, especially given Jeremy Hunt's direct involvement. "It was very, very politicised and challenging to defend. If we had lost it, it would've been very controversial - the Government would've had to rethink their approach and the Secretary of State's position would have been in question. There was a lot riding on it."
He has never turned down a case; most memorably he once represented Marks & Spencer's in a discrimination claim brought by a Jewish woman who'd applied to be a food technologist, but was turned down because she wouldn't eat seafood and meat. His opponent called a Jewish vegetarian food technologist at a pork factory as a witness. "My first question was is this the new definition of chutzpah?"
Over the summer he found himself working on a case that aligned rather well with his principles; successfully defending the Labour NEC over the eligibility criteria for members voting in the leadership contest. Ultimately, this was a tussle between the party's moderates and Jeremy Corbyn's supporters.
"Of all the cases I've been involved in over the past five years it's the only one where I've had 100 likes on my Facebook page and where everyone I know was delighted I was on it," he smiles. "I really wanted to win. It was the first incident over many months in which there was a defeat for the Corbyn camp and it gave a little bit of a sense of joy for the non-Corbynites."
The tone around the case was unpleasant, he says, although he avoided any direct abuse from disgruntled activists. In one of those "small Jewish world" twists of fate, his opponent was David Goldstone, a Jewish QC whose Holocaust survivor mother visits Poland with Sheldon's.
Corbyn's subsequent re-election was disappointing, says Sheldon, an erstwhile Labour donor who, though no longer active in his local party, remains a member. He stresses that Jews should not abandon Labour. "You have to confront the challenge; you have to work with them."
He rejects the idea that Labour is riddled with antisemitism. "There's always been anti-Zionism in it, which can be and sometime is confused with antisemitism," he says, suggesting that such voices have become more legitimate under Corbyn. "There will be further incidents I'm sure, and I very much hope they've learnt their lesson because in reality it's a massive sideshow from what they need to be doing."
In another life, Sheldon would have been a politician, and he enjoys the nitty gritty of the policy conversation. But as chair of New Israel Fund UK, which this week celebrates its tenth annual human rights awards ceremony, his attention is even more fixed on the debate in Israel. The charity works towards a more equal country for all Israelis, Jewish or not and the awards will see three Israeli organisations honoured for their efforts to ensure "the fabric of Israeli society is strong and cohesive".
With established bodies such as the UJIA also campaigning on issues of tolerance and diversity in Israel, he thinks it has become easier to get through to British Jews, although he hopes NIF UK can branch out further to talk to the community as a whole. The job is tougher in Israel.
"Israel is an incredibly polarised society, and there's a lot of you are either with us or against us," he says. "We represent the people who try to hold to account the establishment."
Nevertheless, Sheldon is not pessimistic about the Jewish state's future. "There are hundreds and hundreds of thousands of people there working towards good values, declaration of independence values. Although it looks as though things have shifted in the other direction, there's more nationalism, more extremism, I think the tide will turn," he says. "What NIF does and what I really believe in is you need to be carrying on the work so when things shift you've got infrastructure and you've got civil society."
"That might be naïve," he admits. "But naïve people sometimes win out."
