Not only is Clunie betting against a host of Anderson's favourite stocks, the manager is also shorting shares in Scottish Mortgage (SMT), the UK's largest investment trust run by his 'nemesis'.
The bet against the FTSE 100 listed, growth-focused trust is the natural culmination of Clunie's strategy, characterised as long value and short growth, that has placed the manager on the opposing side of trades with Anderson on a number of stocks.
Among Clunie's biggest shorts are bets against e-commerce giant Amazon (AMZN.O), electric car maker Tesla (TSLA.O) and film streaming service Netflix (NTFLX.O), all large, longstanding and profitable holdings for Anderson.
Clunie said the decision to short Scottish Mortgage arose following a conversation with his colleague Ben Whitmore, UK and global equity income manager, whose value approach places him at the opposite end of the investment spectrum to growth-focused UK-stockpicker Nick Train.
'My alter ego'
'His nemesis is Nick Train,' he said. 'Who is my alter ego? It is James Anderson. I'm short 15 of his long stocks.'
Clunie is sticking with his short on the trust, focusing on Anderson's (pictured) heavy holding in Tesla, a 6.1% position in the portfolio and the fifth largest weighting.
'Why is he the largest Tesla shareholder?' he said. 'My view is he should be smart enough to take his Tesla position down.'
Yet the trajectory of Tesla's shares illustrate the difficulties Clunie has faced. The news emanating from the car maker headed by controversial entrepreneur Elon Musk in recent months has been a seeming gift to bears like Clunie.
Musk has become embroiled in a long-running dispute with the US Securities and Exchange Commission, reaching a fraud settlement with the US regulator after a series of tweets about taking his company private. Now the SEC is claiming Musk has violated that settlement.
And in the the space of one extraordinary week last September, two top executives left the business while Musk escalated baseless attacks on a British diver who rescued children from a cave in Thailand, calling him a 'child rapist', and smoked marijuana on a live web show.
Yet the shares, while 25% down from a December high, are down just 13% over the last year and are up a staggering 630% over the last six.
The bull market of the last 10 years has proved difficult for most absolute return managers, yet the last two years have been particularly painful for Clunie.
Trump weighs on fund
Over that period, Jupiter Absolute Return is down 8%, placing the fund towards the bottom of the Investment Association's Targeted Absolute Return sector.
Clunie acknowledged his 'especially poor' performance in the latest annual report for the fund, covering the year to the end of October.
'We dug a little deeper and believe the reason for the underperformance is relatively straightforward: the promise of tax cuts in the US after Donald Trump's election as president.'
'The expectation of fiscal stimulus at that time unleashed "animal spirits" in markets, which can be summed up as a desire for risk, a desire for glamour.' In other words, lifting exactly the sort of high-growth stocks Clunie is betting against.
Clunie concedes that if stock markets do not shift their dynamics, and growth stocks continue to outpace value companies, it will be painful for his fund.
'What would hurt me is a continuation of what we've seen for the last 10 years,' he said.
It follows that he is positioned in direct opposition to some of the funds that have prospered the most in the stock market environment of the last few years.
While that is most explicit in his shorting of Scottish Mortgage, Clunie is also betting against some of the stocks that have powered the rise of two of the biggest and most successful funds of recent years, Fundsmith Equity and Lindsell Train Global Equity.
Clunie's shorts, according to October's annual report, include Lindsell Train favourites Hargreaves Lansdown (HRGV), Mondelez (MDLZ.O) and Diageo (DGE) alongside Fundsmith picks Coloplast (COLOb.CO), Intuit (INTU.O) and Facebook.
The manager gained some respite from his recent poor run in the sell-off at the end of last year, as the growth stocks he has positioned against sold off the sharpest.
But the dovish signalling from the Federal Reserve at the beginning of this year, sparking a strong start to 2019 for stock markets, has seen his fund slide again.
Clunie said it was difficult to tell whether stock markets were still in a bull market, or had entered into bear territory.
In October and December it appeared we had entered a bear market, he said, but now it was less clear. 'You never quite know it when you're in it,' he said.
'But we know bear market rallies are the sharpest of the lot. And this has been sharp.'