O'Brien Group

O'Brien Group

The O'Brien family's wealth traces to 1914, when Robert J. O'Brien Sr. founded the futures brokerage R.J. O'Brien & Associates, a founding member firm of the Chicago Mercantile Exchange. The family formalized its investment arm in 2009, establishing O'Brien Investment Group in Skokie, Illinois, as a regulated commodity trading advisor and National Futures Association member. The office remains anchored by O'Brien family principals, including CEO and Portfolio Manager John O'Brien Jr. The firm deploys capital through two fund structures that reflect its futures-trading DNA. The OBIG Quantitative Global Macro Fund, launched in September 2017, trades over 50 financial and commodity futures and options markets using a blend of machine-learning trend models and covered-option overlays. The OBIG Pecus Digital Assets Fund, started in January 2021, trades Bitcoin and Ether futures alongside non-directional basis trades and a discretionary basket of smaller crypto assets. Both vehicles seek absolute returns uncorrelated to traditional benchmarks. The office also allocates to direct co-investments and SPVs, with confirmed interests in Sports & Wellness and Media & Entertainment. OBIG operates with a compact team of six professionals covering portfolio management, trading, quantitative research, and risk. The office shares an address with a commercial property at 5215 Old Orchard Road in Skokie. Adjacent vehicles include the John W. O'Brien Family Foundation and the O'Brien Museum of Irish Art and Culture, both overseen by family member Patricia M. O'Brien. The late John W. O'Brien, former CEO and Chairman of R.J. O'Brien, was inducted into the FIA Futures Hall of Fame. The firm's structural differentiator is its identity as a CTA born inside a single-family office. Rather than functioning as an allocator across external managers, OBIG develops and runs proprietary systematic strategies — using the family's capital as anchor LP — with a regulatory registration that permits external capital.