The only other time Simmons raced at
Strade Bianche was back in 2021. Riding amongst the lead group alongside Wout van Aert, Mathieu van der Poel, Egan Bernal, Michael Gogl, Tom Pidcock, Julian Alaphilippe and Tadej Pogacar, Simmons looked set to battle it out for the win.
Sadly for the talented young American, an ill-timed puncture put an end to his hopes of victory and then to make matters worse for Simmons a crash in the second group saw him fall completely out of contention, eventually finishing 54th nearly seven and a half minutes off the race winner. As he reflects, "Very good legs, very bad luck."