Aaron Massey

Aaron Massey graduated from Northern Illinois University with a bachelor's degree in finance in 2008. He had been playing poker since 2002, often driving to Indiana casinos with his brother Ralph's ID as a teenager. After the financial crisis and the rise of online poker, Massey left the finance world in 2009 to pursue a professional poker career. He spent countless hours grinding online, playing up to 12 hours a day on multiple tables, under the mentorship of renowned online player Kevin “Bel0wab0ve” Saul. The 2011 Black Friday crackdown on online poker in the US forced Massey back to live tournaments, where his natural skills shone.

Massey’s largest live cash came in August 2012 when he won the WinStar World Casino River Poker Series Main Event for $651,559. Earlier in 2012, he also won a Pot-Limit Omaha event in Chicago for over $40,000 along with a Main Event seat. He was named the 2014 Heartland Poker Tour (HPT) Player of the Year and was listed as one of seven "Ones to Watch" for Season XII of the World Poker Tour (WPT). As of 2025, his total live tournament earnings exceed $6.6 million, placing him among the top 350 all-time money earners. Massey has 15 live titles, including multiple WSOP Circuit rings. He also holds the distinction of being one of the few players to cash in the WSOP National Championship after accumulating enough circuit points in 2012.

At the World Series of Poker, Massey has over 60 cashes and 4 final tables, with total WSOP-related earnings exceeding $3.3 million. His deepest WSOP run came in 2014 when he finished third in a $1,500 No-Limit Hold'em event for $255,209, the highest WSOP cash of his career. He also owns three WSOP Circuit rings from events in Hammond, St. Louis, and other stops, with 73 circuit cashes worth over $500,000. In 2012, he earned enough points from circuit finishes—including a 6th and 15th place—to qualify for the WSOP National Championship, though he did not win the title. Over his career, Massey has demonstrated resilience, coming close multiple times to a WSOP bracelet but falling just short; he has zero bracelets but remains a consistent deep-run threat.

Massey has been open about the mental challenges of poker. In his blog series on the Chicago Poker Club, he detailed the importance of emotional control during downswings. In the summer of 2012, he suffered a $40,000 downswing over two months with no WSOP cashes and a single Venetian cash for $2,795. Despite playing well, he emphasized learning from mistakes and maintaining confidence. During a WSOP Circuit series in Biloxi, he made a conscious effort to laugh off bustouts, a sign of growing maturity. He also wrote about a 30-day stretch in early 2012 where he ran extremely bad, missing the money in multiple tournaments on stone bubbles—including a hand where his KK lost to AA on the money bubble at the Borgota Winter Open. These experiences shaped his philosophy: he believes live poker is his calling and that resilience is key.

Massey considers himself a live poker specialist who thrives in the felt environment. He learned fundamentals from online play but feels his edge is greatest in live settings. His style is aggressive but controlled; he focuses on making few mistakes and capitalizing on weaker players. He often reflects on the importance of bankroll management and the willingness to skip over-priced events when emotionally drained. Massey values the journey of constant improvement and has cited mentors like Kevin Saul for online strategy and friends like John Dolan and Kurt Jewell for live tournament insights.

Massey and his older brother, Ralph Massey, are the founders of Big Cock Poker, a poker apparel company based in Chicago, Illinois. The brand is known for its humorous and bold designs, and the brothers run the business together. Massey resides in Chicago and continues to play in major tournaments worldwide. He also contributes regularly to poker media, writing candid blog posts about his experiences on the circuit, sharing both triumphs and failures to help other players learn from his journey.