Back in 2014, Howard was the starting shortstop for the Jackie Robinson West team that reached the Little League World Series championship game. As part of that journey, the city held a rally to celebrate Jackie Robinson West. Cubs president of baseball operations Theo Epstein spoke at it and had a message for Howard and his teammates.
"Time definitely flies," Howard said. "I remember that day. We had this little parade around the city, then went over to Millennium Park, I'm pretty sure. He gave the speech. I just remember, the video when it resurfaced, I had forgot that he said that. But then looking at, it just brought back memories. He basically spoke it into existence. He said 2023, which would've been after three years of college. But it happened earlier, 2020. He basically spoke it into existence. So it's pretty funny. It's a great story. I'm excited. It's a blessing to be chosen by the Cubs and have this opportunity."