This marks a low point in a year of struggle for Gross’ Janus Global Unconstrained Bond Fund, which has seen a loss of 1.9% since the famed bond investor joined Janus Capital in October last year from Pimco, the firm he co-founded four decades ago. Gross’ current performance means his Janus fund ranks near the bottom quintile of its peer category this year, according to Morningstar.

Soros’ money was in Quantum Partners fund, a private investment vehicle run by Gross that mimics the strategy in his Janus’ fund. A $490 million outflow was first mentioned by trade publication Pensions & Investments, and later was confirmed to be Soros by the Journal.

The move can be seen as doubly painful because Soros’ investment was trumpeted as a stamp of approval for Gross, who was dumped from Pimco after apparent internal clashes with management. He has since launched a lawsuit against Pimco alleging wrongful dismissal.

One year ago, Gross took time to personally mention Soros’ investment on Twitter (TWTR) through the Janus’ social media account:

Gross: (1/2) We are honored to be managing a new unconstrained strategic account for Soros Fund Management LLC. http://t.co/roWs8EBnYf

— Janus Henderson Investors (@JHIAdvisors) November 20, 2014

This represents a further hit on Gross’ previously stalwart reputation as an investing savant. During his time at Pimco, Gross’ main fund, the $162.8 billion Pimco Total Return, beat 96% of peers over 15 years, according to Morningstar. The withdrawal of Soros’ money also hits Gross’ pocket hard, as the Janus Global Unconstrained Bond Fund, which has $1.4 billion in assets under management, holds more than $700 million of Gross’ personal money, according to Reuters.

“The fund has struggled to gather assets. For investors who had faith in Gross, including Soros, they have been disappointed,” Todd Rosenbluth, director of ETF & Mutual Fund Research at S&P Capital IQ, told Reuters. The news, however, had no net negative effect on Janus Capital’s (JNS) share price.