As the Pittsburgh Pirates closed in on a franchise-record, eight-year, $106.75 million contract extension with Bryan Reynolds, one word kept going through Ben Cherington’s mind.

Another general manager, “someone who did the job I’m in now for a lot longer and was way more accomplished,” shared with Cherington a secret to success: Find players you trust.

The Pirates trusted Reynolds was worthy of the contentious negotiations that included a trade request and publicly expressing his frustration that he was only seeking a “fair deal for both sides” but ultimately led to the club investing its first nine-figure deal in the 28-year-old outfielder.

“I’m just really excited about what we’re building. What the team can be, what we’re already doing, and just what the future could hold here.” pic.twitter.com/odjoFZh1Cm

— Pittsburgh Pirates (@Pirates) April 26, 2023

The contract, which runs through 2030, includes a $2 million signing bonus, buys out two years of arbitration and six years of free agency and is worth a potential $124.75 million. Reynolds will make $6.75 million this season, completing the second year of a two-year contract signed last April. He will earn $10 million in 2024, $12 million in 2025, $14 million in 2026 and $15 million per season from 2027-30. There is a $20 million club option in 2031, with a $2 million buyout.

“Ultimately you pursue these things because you trust the player,” Cherington said. “We trust Bryan. At a basic level we trust Bryan because of what he’s already done. We trust him because of the way he plays. We trust him because of the choices he makes on and off the field. We trust him because we know how hard he’s working to continue to get better all the time. We trust his focus. We trust his toughness.

“Not only does that show up on the field, but that showed up through this process. Bryan himself demonstrated focus and toughness through this process. For all those reasons, we trust Bryan. When you really feel that way, that gives you a confidence to pursue it and make these kinds of recommendations.”

Pirates chairman Bob Nutting trusted that Reynolds was true to his word when he stated he wanted to stay in Pittsburgh. Despite the trade request, Reynolds left the door to negotiations open past his self-imposed Opening Day deadline when the parties came to an impasse over the inclusion of an opt-out clause after four years.

Nutting wanted to build a trust with Reynolds that would change his public perception as an owner who would rather trade top players than pay them. Nutting assured Reynolds, publicly and privately, how much the Pirates appreciated and respected his hard-nosed play that matched his no-nonsense personality.

Not only did Nutting speak with Reynolds at spring training before batting practice at Pirate City in Bradenton, Fla., and at the home opener but also had a private 45-minute conversation in a board room at PNC Park. Their conversations kept the negotiations going, resulting in a deal where the sides, once $50 million apart, met in the middle. The deal includes a limited, six-team no-trade clause, also a first for the Pirates.

Here to stay. ???? pic.twitter.com/qtA0TiDtE3

— Pittsburgh Pirates (@Pirates) April 26, 2023

“Moving from a trade request to a signed contract is a big step,” Nutting said. “Part of that is his faith in the organization, his faith that we’re moving in the right direction. Part of that has to be a relationship that we have that’s open and supportive.”

When formally announcing the contract Wednesday afternoon, Nutting turned to his left and thanked Reynolds for placing his trust in both the negotiating process and the rebuilding plans that had the Pirates go from back-to-back 100-loss seasons to atop the NL Central standings.

“I always believed through the process an agreement was possible because of your desire to be a part of something really special in Pittsburgh,” Nutting told Reynolds. “And frankly, combined with our desire that you’re part of this next chapter of the Pirates franchise. I think it’s a great chapter. We’re in a wonderful spot right now, and you deserve to be a part of that.”

Perhaps no one in the Pirates organization is as excited about Reynolds being locked up long-term than manager Derek Shelton, who called the contract “tangible proof” of the trust. Shelton now has cornerstones in Reynolds and third baseman Ke’Bryan Hayes, who signed an eight-year, $70 million contract last April, to build a team around.

“To be able to commit that amount of years, that amount of money to a player, yes, that’s really important,” Shelton said. “It’s really important that our players see it. I think it’s really important that the industry sees that there is something that we outlined and we are following through with it.”

The nature of the negotiations showed the “extremely stubborn” side of Reynolds, Shelton said, meaning it in a “very complimentary way.” Shelton noted the intensity of Reynolds’ at-bats and how he got ejected for arguing balls and strikes when the Pirates had a 9-1 lead at Colorado.

“He believes what he believes in, and I think this kind of translated into this negotiation,” Shelton said. “Ultimately, his belief is he wanted to be here and, as Ben and Bob both highlighted, this was driven by Bryan and his willingness, the want to be a Pirate. But, yeah, he is stubborn in a beautiful way.”

As much as he wanted to be paid like a star, Reynolds shies away from public attention, so sitting on the dais in front of cameras with his family, teammates, baseball operations, coaching and support staffs in attendance clearly made him uncomfortable. So Reynolds appeared relieved, more than anything, that he can get back to concentrating on baseball.

“Every time I stepped on the field, I was focused on the task at hand, but there’s always that little piece in the back of your mind that’s thinking about it. I’d be a liar if I said it didn’t weigh a little bit on me,” Reynolds said. “I’m pumped to have the situation resolved and be resolved in this manner to where we’re all sitting up here together and talking about the future.”

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