James Harden surpassed Ray Allen in more than one aspect. Besides making career 3-pointers, The Beard has at least $65 million more in the bank than the NBA legend. But hey, building and growing a net worth of $100 million is no small feat by Ray Allen. 2 NBA championships, 10 All-Star appearances, the 3-Point Contest title, and a glorious resume made Ray-Ray worthy of a massive paycheck and brand deals. It’s his journey of smarts and triumph that makes his net worth a massive accomplishment.

Retired for a decade, Ray Allen has a lot to show for his success. We look at his career by the numbers.

Rookie Ray Allen’s bold business moves from the start

A military child with a British accent, 15-year-old Walter Ray Allen Jr. was attracting college offers at Hillcrest High School’s varsity team. The winning legacy of the University of Connecticut ended up the winner. Under Ray Allen, the Huskies made their third consecutive Big East Conference regular season title and third consecutive NCAA Tournament appearance.

With an awe-worthy collegiate career, Allen entered the 1996 NBA draft. The Minnesota Timberwolves selected him fifth overall and immediately traded him to the Milwaukee Bucks for Stephon Marbury. The first-round pick got a worthy rookie-scale contract – $6.2 million for 3 years. Marbury, who was selected before him, got an identical contract.

HIs career graph was upward from the moment he outscored Allen Iverson in his NBA debut. In the 1997–98 season, Allen started all 82 games for the Bucks. He made a strong case to demand a massive raise in 1999 – an eye-popping $70 million – from the Bucks, making him the highest-paid player of the franchise at this time.

Note: analysts at the time predicted he could’ve made $84 million. He hired the famous Johnnie Cochran (the same attorney who defended OJ Simpson had become a sports agent in his later career) for $500 an hour to study the Bucks’ offer. It was an unorthodox move to avoid a sports agent commission that could’ve been in the seven figures. It became a brilliant example of smart business moves in the league. Allen went from a $1.7 million salary as a rookie to upwards of $9 million after his third year.

He left $14 million on the table but he earned that when he arrived in Seattle after 2003. The Supersonics gave him an extension worth $85 million in 2005, just before he became the 97th player to make 15,000 points and made all-time 3-point records.

With that resume, he arrived in Boston and led the Celtics to its 17th championship.  That was worth a raise and his salary at his prime was around $18 million. He took a pay cut when he signed an extension in 2010, bringing his salary to $10 million which it was a decade earlier.

In 2012, he arrived in a stacked Miami Heat bursting with star power. He agreed to a $6 million deal for the final two years of his career. But the sweeter part of this move was retiring with his second chip.

Ray Allen’s Air Jordan maneuvers

3-point records and Slam Dunks make a worthy brand ambassador. Nike saw its value right away for its own branching ambitions. For young Ray-Ray, picking Michael Jordan was easy. As a rookie in 1996, he signed with the Jordan Brand. The namesake himself was in the middle of two three-peats and Allen had gone against Michael Jordan in his fair share of games. Allen was the Jordan Brand’s first signing as an established Nike subsidiary.

Sugar wore Air Jordans his entire career which really boosted his popularity points. Allen admitted everywhere he went, loved ones and fans asked him for Jordans. Opponents asked for his worn Air Jordans after a game or two. From wearing AJ13s in the ’98 flick He Got Game to auctioning his rarer pairs, Allen made wearing the Jumpman logo an homage to the man himself.

Ray Allen, the lowkey businessman

Like many retired NBA pros, Ray Allen diversified into businesses after basketball. Unlike Shaquille O’Neal’s bold moves or Carmelo Anthony’s unique ventures, Allen kept it safe in the business world.

One such move that doesn’t get talked about enough is Grown, a restaurant chain originated by his wife, Shannon. Based of Shannon Allen’s nutritious recipes for Ray and their kids, Grown serves a healthy and organic menu at its Miami locations. It took six years of planning before officially launching in 2016.

Besides that, he’s also gone the traditional route with real estate investments. Some of his most interesting purchases are his own residences, including an 11,093 square feet home in Boston. He bought it in 2007 for $4.6 million and sold it for $5.2 million, a neat profit, in 2012. He also owned a spectacular manse in Coral Gables, Florida worth $11 million.

His movie career was short-lived and he published one book. But he has the sporadic media appearance to be a semi-NBA analyst and he is a busy touring speaker.