The Pitino family made for a big storyline over the weekend, but there was someone else who was an even bigger focal point of the conversation.
On Saturday, Rick Pitino’s St. John’s Red Storm faced Arkansas in the second round of the NCAA Tournament. Arkansas won 75-66 to knock Pitino’s squad out of the tournament. The next day, Rick’s son Richard was leading New Mexico against Michigan State in the second round of the tournament. His Lobos lost to the Spartans 71-63.
Rick had traveled from Providence, R.I., to Cleveland, Ohio, to watch his son’s team play. He was a fan in the stands and was shown on TV frequently. But he’s not what the fans were looking at when they saw him on TV.

Just a video of Rick Pitino supporting his son nothing else relevant in the background pic.twitter.com/eLsmZDfBob
— Barstool St. John’s (@SJUBarstool) March 24, 2025
Apparently Rick Pitino is in this photo. https://t.co/lLgVW3jkoR pic.twitter.com/R8msl8wbV1
— Owen (@75toRupp) March 24, 2025
Of course, the woman’s presence behind Pitino led to some Karen Sypher jokes.
You can almost see on Pitino’s face that it’s taking everything in his power to not turn around and ask this woman if she likes Italian food because he knows a good place and the owner will let him lock up before he leaves. pic.twitter.com/TUZQ2Jt9ry
— Jax Teller (@jaxteller_KY) March 24, 2025
Sypher had gone to prison for extorting Pitino. The two had engaged in a highly publicized sexual affair prior to the extortion attempt.
Was someone sabotaging Pitino with the placement of that woman? Or was it just a coincidence? Either way, the weekend did not go well for the Pitinos, as both of their teams lost in the second round.