Pittsburgh confirmed on Oct. 5 that Simon was among players who did not receive a qualifying offer. He became a free agent on Oct. 9.
The 26-year-old took to Instagram to thank the Penguins for his tenure with the franchise and also touch upon what is to come:
View this post on Instagram
I want to thank the Pittsburgh Penguins organization for everything they did for me. I appreciate every second of my time in there. Its a beautiful hockey town with great fans and amazing people all around. Thank you for welcoming me with open arms. That being said I cant be any happier and more excited to become a member of Calgary Flames organization #CalgaryFlames
The Penguins selected Simon 137th overall in the 2015 NHL Draft, and he made his official league debut in March 2016. His last two seasons were his best with Pittsburgh, as he tallied eight goals and 20 assists in 2018-19 and followed that with seven goals and 15 assists across 64 games during the 2019-20 season that was halted on March 12 because of the coronavirus pandemic.
As Taylor Haase wrote for DK Pittsburgh Sports, Simon didn't participate in the summer NHL restart because he underwent shoulder surgery on April 29 that is expected to keep him sidelined up to seven months. Jan. 1 is currently the tentative date for the start of the upcoming NHL season, and Simon should be ready to go for the Flames by then barring an unforeseen setback.
In 173 regular-season games with Pittsburgh, Simon compiled 19 goals and 45 assists for 64 points. He notched four assists in 12 Stanley Cup Playoff games.