The second conversation occurred weeks later, near Wright's home in coastal Virginia. Over a round of golf and a late lunch, Wright was "brutally honest" in questioning general manager Sandy Alderson about the future of the franchise, grilling him on the organization's long-term baseball operations plan.
The final conversation took place Tuesday at The Palm restaurant in downtown Nashville. At a celebratory dinner, Wright and his family joined Wilpon, Alderson and other members of the front office in toasting the eight-year, $138 million deal that will keep Wright in blue and orange through 2020.
"I can honestly say I've never pictured myself in a different uniform," Wright said after the Mets officially announced his contract extension Wednesday at the Opryland Hotel. "It wouldn't be as meaningful if I were to win somewhere else."
Now signed through his age-37 season, Wright is confident he can win with the same team that drafted him and launched his career. That notion, even more than the richest contract in team history, is why he decided to return; had Wright waited a year and tested free agency, he could have earned similar -- or greater -- dollar figures elsewhere.
This marriage was more about a mutually beneficial long-term commitment.
"David's not going to make a decision of this magnitude based on chit-chat during a golf match," Alderson said. "It really was a function of a two-year relationship with me."
Wright's new deal includes a full no-trade clause and actually reduces his salary in 2013, before the payments balloon during the middle years of his deal. The resulting short-term flexibility could potentially help the Mets sign R.A. Dickey to his own contract extension, add a higher-tier free-agent outfielder or swing an otherwise prohibitive trade.
The deal is structured like a bell curve so that the Mets will also have flexibility in its later years, when Wilpon noted it is "realistic" to assume Wright's production will decline. If Wright wants to sign another contract after this one to remain a lifetime Met -- to "play a ninth year or a 10th year," in Wilpon's words -- he will not have to absorb a monumental pay cut to do so.
To be certain, in terms of dollars and cents, it is a monumental commitment for both sides. The Mets made it only because Wright's personality matches his resume; Wilpon thanked Wright's parents for instilling in him the type of values that have made him a loyal soldier to the organization, as committed to helping off-field causes as he is to winning.
"It solidifies for the fan base that our favorite player right now, a guy who's only worn a Met uniform, is going to be here for the long term," Wilpon said. "If [his parents] didn't raise him to be the man he is, we wouldn't have committed to him. It's not sappy. It's something that we did think about."
Wright's father, Rhon, his mother, Elisa, and his girlfriend, Molly Beers, attended Wednesday's news conference alongside agents Sam and Seth Levinson and Keith Miller, huddling off to the side while Wright spent most of his afternoon on a whirlwind media tour. Arriving at the Opryland in a blue-and-white plaid shirt and orange tie, the third baseman slipped on a new royal blue alternate jersey after the Mets made their announcement.
Now the clock is on Wilpon and Alderson, who aim to make good on their promises to Wright. Those vows include an expanded payroll in the coming years and an overall commitment to winning, surrounding their third baseman with championship-caliber players. Whether over golf with the GM or late-night burgers with the owner, Wright has displayed a keen interest in the organization's finances and farm system, peppering Wilpon and Alderson with those concerns.
Wilpon assured Wright not only that the team is "very stable" financially, but also that the Wilpon family will own the franchise for years to come. Weeks later, Alderson told Wright that pitchers Matt Harvey and Zack Wheeler represent only the beginning of a talent pipeline that should lead to rapid improvement.
"I asked as many tough questions as I could," Wright said. "And in the end, I obviously got the answers that I wanted to hear."
As a result, Wright is now well on his way to being a Met for life. Both parties hope only that the next eight years unfold as they envision.
"I take a lot of pride in putting on this uniform on every day," Wright said. "I take a lot of pride in going out there and trying to play hard in front of those fans every day. And there's a lot of good times to come."