Described as having the ‘insights, the wisdom and the humor’ to help former First Lady Michelle Obama through the trials of the White House, Craig Robinson flew under the radar during his sister’s time in the spotlight.
Despite coming from one of the most famous political families in America, Robinson is far from a household name. But he’s enjoyed a life nearly as fascinating as his sister’s and has turned his hand to everything from finance and politics to the NBA and broadcasting.
The 62-year-old re-appeared on screens this week as he and Michelle launched their new podcast, ‘IMO with Michelle Obama and Craig Robinson’, where the brother and sister will share their thoughts on ‘a lot going on in the world right now.’
The siblings grew up extremely close on the south side of Chicago, and when Michelle announced the podcast this week, she wrote that her brother ‘is one of the people I turn to whenever I have anything on my mind.’
‘He always has the insights, the wisdom, and the humor to get me through anything,’ she wrote.
But before Michelle had met her future president husband, Craig was making a name for himself as a standout basketball star for Princeton University in the early 1980s.
And while he was even drafted into the NBA in 1983 – although he never played a game – perhaps Robinson’s most famous basketball performance came when he played against Barack to judge his character as a suitor for his sister.
Craig Robinson launched a new podcast this week with his former First Lady sister Michelle Obama, following a career that has taken him everywhere from the NBA to Wall Street
The siblings grew up poor in the south side of Chicago, but Robinson said they were blissfully unaware of their poverty and ‘never wanted for anything’
A two-time Ivy League player of the year, Robinson trained with Michael Jordan in 1983 when he prepared for his comeback from injury, and at the time he was talked about in the same conversation as the now-NBA legend.
Robinson was drafted into the NBA in the fourth round by the Philadelphia 76ers, and after failing to make the cut, his only professional appearances were for the Manchester Giants in the British Basketball League for two seasons.
While not known for seeking the spotlight, Robinson became well known during the 2008 presidential election for the role he served when Michelle first started dating Barack in the 1990s.
Robinson recalled that when Michelle first began their relationship, she asked her brother to play basketball with the future president to gauge his character.
He said the two became fast friends because of the way Barack played, telling Esquire: ‘He was quietly confident, which means he had good self-esteem without being cocky.
‘He was certainly a team player — he wasn’t a pig, he passed when he was supposed to pass, and he cut when he was supposed to cut. To me, that speaks to a lack of selfishness.
‘He had natural leadership ability, because he didn’t just pass me the ball because he was dating my sister. Whenever a player gets tired, he reverts back to the player he truly is. That’s how you tell. And we played for hours. That’s how I could tell.’
Robinson was a standout forward for Princeton University, becoming a two-time Ivy League player of the year. Although he was drafted into the NBA for the Philadelphia 76ers in 1983, he never played a game
Robinson famously played a game of basketball against Barack Obama when he first started dating Michelle so he could judge the future president’s character
Following his time in Manchester, Robinson enjoyed a brief spell as a coach for the Illinois Institute of Technology, before he put his Princeton University degree to use as he pivoted to a career in finance in 1990.
Robinson rose through the banking world over the next decade, working as a trader, managing director and partner at a number of banks, spending the majority of the decade with Morgan Stanley.
He remained close to Michelle as she also graduated from Princeton in 1985 and became a renowned lawyer in her own right.
After their father died in 1991, the older brother became something of a father figure to the future First Lady, even walking her down the aisle when she married Barack.
Despite making a substantial salary, Robinson left the finance world in 1999 to return to his passion for basketball, and became an assistant coach at Northwestern University, taking a reported 90 percent pay cut.
The siblings, seen smiling during a recent meal out in Los Angeles in February 2025, have remained close throughout Michelle’s time in the spotlight
Robinson and Michelle grew up in humble beginnings in Chicago, the children of water plant worker Fraser Robinson III and secretary-turned-stay at home mom Marian Shields
Robinson and Michelle’s meteoric rise is all the more impressive given their humble beginnings in Chicago,
Their father Fraser Robinson III was a water plant worker, while mother Marian Shields was a secretary-turned-stay at home mom.
Money was tight, but Robinson said in his memoir ‘A Game of Character’, that his childhood was a very happy one.
He explained: ‘In reality, I had no clue that we were poor and wouldn’t until leaving home for college.’
‘But what I did know was that I never had to want for anything that I needed or wished for.’
In a 2023 essay for Newsweek, Robinson said that although his family ‘didn’t have a whole lot of money’, he was blissfully unaware because ‘our house was always filled with love.’
‘We ate out every now and then and went to the movies. So, I was happy – I didn’t feel like I was missing anything,’ he wrote.
A father-of-four, Robinson shared two children, Avery and Leslie, with his first wife, Janis Robinson, who he split with in 2000.
Robinson then met his second wife Kelly McCrum the next year at the NCAA March Madness Final Four event, and the two tied the knot in 2006 and had two sons, Austin and Aaron.
Robinson, a father of four, married his second wife Kelly Robinson (seen together in 2016) in 2006 after meeting at the NCAA March Madness Final Four event
Robinson’s daughter Leslie was drafted by the WNBA’s New York Liberty in 2018, which he said left him ‘happy, excited and surprised all at once’
In 2018, his daughter Leslie carried on the family legacy in basketball when she became the first woman from an Ivy League college in two decades to be drafted into the WNBA by New York Liberty.
Robinson admitted his whole family – except for one of Leslie’s young brothers – were stunned by the draft, saying he was ‘happy, excited, and surprised all at once.’
‘The only one that truly thought that Leslie was going to get drafted was her 8-year-old brother. I am so proud of her,’ he said.
In 2022 Robinson again made headlines through his children, but not in such a positive way.
Robinson and his wife Kelly filed a lawsuit against their children’s private school, the University School of Milwaukee, accusing the institution of racism and for expelling their sons in retaliation to the couple’s criticism of the school.
‘The first thing we noticed was a repeated use of racial and ethnic stereotypes in actual classroom assignments,’ Robinson told CNN at the time.
The school denied allegations of ‘inequity or discrimination’, and shot back in a statement: ‘We cannot and will not tolerate persistently disrespectful, bullying, or harassing behavior directed at our devoted and hardworking teachers and administrators.’
The lawsuit was ultimately dismissed with prejudice in November 2024, and a joint statement between the parents and the school said the ‘parties have resolved the matter.’
Robinson led a successful banking career in the 1990s, mostly with Morgan Stanley, but went back to basketball coaching for a fraction of his salary to re-ignite his passion for the game
After his return to basketball coaching in 1999 on a fraction of his banking salary, Robinson was an assistant coach at Northwestern University until being promoted to head coach of Brown University in 2006.
Robinson hit the campaign trail with his sister and Barack two years later, including giving a number of speeches and often talking of their pickup basketball game a decade earlier.
But there were blips in Robinson’s coaching career too. He was fired as the head coach of men’s basketball at Oregon State University in May 2014 over his team’s poor performance.
Robinson was being paid around $1.3 million-a-year for the role had three years remaining on his salary, meaning he was owed $4 million.
Following years as a coach, most notably at the Oregon State Beavers, Robinson moved up the hierarchy in 2016 when he was hired as vice president of player and organizational development by the Milwaukee Bucks.
The next year, he left the Bucks to join the New York Knicks, where he served as vice-president until 2020.
Robinson also became well known during his brother-in-law’s presidency as a college basketball analyst for ESPN, starting in 2014.
In July 2020, Robinson rose to his current job, when he was named as the executive director of the National Association of Basketball Coaches.