With the regular season right around the corner, the 10-year vet and All-Pro was entering the final year of his contract, and talks between his agent and the organization that drafted him with its first pick in 2011 were dead.
The Steelers don't negotiate contracts during the regular season, and the window for the defensive tackle to receive a contract that would enable him to retire a Steeler was rapidly closing.
But after Heyward's early morning meeting with team owner Art Rooney II, the two sides reached an agreement Sunday night. Heyward will be a Steeler through at least 2024.
"There was a time where this was almost dead, to be completely honest," Heyward said. "I was getting ready for farewells and getting ready for my farewell tour and this being my last ride, but I'm excited to get this done.
"I've always wanted to be a Pittsburgh Steeler, nowhere else, I couldn't see myself being anywhere else, but I had to be ready for that reality."
With a deal that totals $75.1 million over five years, Heyward no longer has to worry about that becoming a reality. As the two sides grew closer to reaching an agreement over the weekend, Heyward went to the Steelers' UPMC practice facility Sunday morning and had a conversation with Rooney. It reaffirmed the conversation he had with Rooney earlier in the offseason when he told him that he was locked in on the season no matter what -- but he wanted to remain a Steeler.
"I won't divulge what was said, but me and Mr. Rooney got to talking, and you know, I'm just appreciative of him," Heyward said. "I understand it's a family business and I understand how serious he takes this. But you know, along with that I wanted to be a Pittsburgh Steeler and he made that happen for me."
Waiting for the new contract wore on Heyward, who went through this process once before, five years ago, and landed a six-year, $59 million deal. This time, though, he has two young children and is managing life in a pandemic. Faced with an uncertain future and the possibility of moving his family away from his hometown and extended family was stressful.
"I am a very emotional person, and I feel with my heart a lot, so quietly I was trying to distance myself a little bit and I was trying to prepare if there was a moment that I wasn't going to be a Pittsburgh Steeler -- not to say that I didn't want to be, but I had to wrap my head around this being the last ride," said Heyward, who added that his family would say he's "been a bit of a headache."
When Heyward last spoke with reporters three weeks ago, he expressed frustration that NFL business was being conducted around the league, yet there was still no movement on his deal.
After that, Heyward's agent, Michael Perrett, started working to negotiate the contract with the Steelers organization.
With the new deal, Heyward will more than likely retire a Pittsburgh Steeler, enjoying a stability in his NFL career that his dad, Craig "Ironhead" Heyward didn't have as he played for five teams in an 11-year professional career. That wasn't lost on Heyward, who reflected on his late dad's career when he was surrounded by family at his grandmother's birthday Sunday afternoon.
"To be such a different situation than what my dad goes through, always feel like I am competing against him and I kind of like it that way -- it lets me know that he's still there and it keeps me grounded," Heyward said. "But to be in a city where I was born, and I have family has meant a lot to me. But not only that, it's a city in which I am indebted to the community, and it's a city that I love playing for."