Recently I’ve become enamored of “bond king” Jeffrey Gundlach after seeing a couple interviews with him. This led to going down a number of rabbit holes and bringing back some vintage drama for you guys.

For those of you who don’t know, Jeffrey Gundlach runs a massive bond fund ($147B assets under management) called Doubleline out in California. He’s also a polymath who left his PhD program at Yale after two years after an argument with his advisor, an art expert (Mondrian in particular) & former drummer in a rock band (he left to go into investment management to pay the bills). Basically really fucking cool.

Well, before he started Doubleline, he was CIO at a firm called TCW. The executives got wind that he was planning on leaving to start his own firm & suddenly showed up with a bunch of lawyers and fired him. Within a week, his bond fund was up and running, taking virtually his entire department with him. TCW sued him for various things including IP theft (a thumb drive was smuggled out in his secretary/girlfriend’s bra). They also decided to leak some embarrassing details in the court filings, namely what was found in his second office: drugs, 12 sex toys, 34 hardcore pornographic magazine and 36 hardcore porn VHS and DVDs.

(What they didn’t mention is that this came from a private office of his own in Santa Monica, that he paid the full rent on. My understanding is that it was just an apartment with an IT set up for TCW—pretty slimy on their end to leak this IMO)

Many people thought it was a set up for slander. A list of contents leaked:

DVDs: Asian Office Sluts Weapons of Ass Destruction Buckets of Cum Big Butt Backdoor Babes 3 Ass Traffic Volume 2 Evil Anal 8 Gang Bang My Face Sloppy Hoes Squirt In My Gape Swallow My Pride 2 The Art of Female Ejaculation The Bondage Nookie Court A Trip Down Mammary Lane Deep Inside Dirty Debutantes Dr. Fellatio 16 Sexual Devices: black restraining device brown rubber penis, 6 inches cardboard with pink and black straps for restraining chrome penis, 6 inches, in red velvet bag glass penis, 8 inches, in black velvet bag glass penis, 7.5 inches, blue velvet bag with tag 'phallic' KY washing liquid with purple rubbing device Sexy Slave Kit For Amazing Sex pink and black strap restraining device rubber penis-shaped sexual device Drugs: baggie containing green "brown leafy substance" bag labeled "medical use only" bag labeled "90210 kush"

The court threw this part of the TCW suit out, but what did the mad man do? He fucking admitted it anyway in a letter to his new investors.

If that weren’t based enough, he counter sued TCW and won/settled in his favor.

Then, in a massive fuck you, 3 years later he threw a party to celebrate the success of his new firm at a restaurant in the lobby of TCW.

The guy is a fucking legend.