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The conversation that turned Brodie Van Wagenen from agent to general manager happened over the course of a two-and-a-half-hour breakfast in early October, as Mets chief operating officer Jeff Wilpon gauged whether or not his friend would be interested in running the major league team owned by his father. Wilpon had already spoken to Van Wagenen, the co-head of the baseball division at CAA Sports, earlier in the year to see if he had any recommendations for New York’s vacated GM position. The idea was to find some under-the-radar options. Instead, Wilpon says, he landed on a bigger idea: Offering the job to Van Wagenen himself.

After some deliberation, discussion began in earnest during that breakfast and Van Wagenen decided to take the leap. A few weeks later, the job was his, after he beat out several other candidates and emerged as the choice from a final three of himself, Rays senior vice president of baseball operations Chaim Bloom, and former Brewers GM Doug Melvin. On a cold and clear Tuesday afternoon in Queens, the Mets made it official, introducing Van Wagenen at Citi Field. One of the most demanding, high profile and difficult management jobs in the sport now belongs to a former agent with zero front office experience—a selection curious, controversial and fraught with risk.

“I recognize I am not the path of least resistance,” Van Wagenen said in his opening remarks, and that’s quite the understatement. In hiring him, the Mets have staked their future on a great unknown, and put the task of getting the team back on the right track in the hands of someone who’s never attempted such a thing before. Van Wagenen, meanwhile, has attached himself to a franchise and ownership group that shoots itself in the foot so often that it’s a miracle there’s anything left to aim at. Why, then, is this the pairing that each has chosen?

The answer remains opaque. Asked what made Van Wagenen the choice, Wilpon didn’t provide much in the way of specific detail: “Brodie was the frontrunner for us because of what he talked about in terms of collaborating, his excitement, his feeling of what he could do with this organization with where we are now and going forward.” As for Van Wagenen, he too stuck to platitudes, speaking of “being part of a new community and embarking upon new challenges to accomplish new goals.” What made him the best person for the job, or what attracted him to this particular team, remained a surface-level topic.

It’s a move that feels all the more odd when you consider the potential pitfalls. Van Wagenen has divested himself of his financial ties to CAA, but while there, he was the representation for several established major leaguers, including Mets stars Jacob deGrom, Noah Syndergaard and Yoenis Cespedes. Such proximity helped make him a familiar face to the Wilpons, but it also raises questions as to how he and the team will negotiate with those players. In his presser, Wilpon said that Van Wagenen would have to recuse himself from contract negotiations on deGrom and others, though he declined to say more than that. Further complicating things is Van Wagenen’s public proclamation back in July that the Mets, as they stumbled through another losing season, should either trade their ace or sign him to a long-term deal. Asked about deGrom on Tuesday, Van Wagenen quipped, “I didn’t expect that question,” but left it at, “I hope to keep him for a long time.”

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Then there are the legal and ethical quagmires Van Wagenen must avoid as a former agent who now represents the other side. What happens with the knowledge he has of players and the information they’ve given him? As an agent, Van Wagenen’s chief concern was maximizing his client’s worth; as a GM, he must find a way to make the player happy and also do what’s financially best for the organization. That’s a conundrum further clouded by the perpetually precarious financial state of the Mets, who carry a payroll more befitting a small-market team and whose owners seemingly hate to be separated from their money.

“We’ve talked about spending and where we are now,” Wilpon told reporters. “He’s totally comfortable about where we’re going to be. We haven’t talked about a specific number yet, but he knows he’s got latitude to make moves.”

That’s not exactly a proclamation to open the coffers—notable ahead of a free-agent period featuring two superstars in Manny Machado and Bryce Harper, who will each command contracts approaching the GDPs of small island nations. But vague promises ruled the day on both sides. “I intend to be talking to every free agent on the market,” Van Wagenen said when asked about Harper, Machado and whoever else might pique his interest this winter as a newly minted team executive. “I expect to be in on every free agent, and if they fit on our roster, we’re going to go after them.”

Then there’s the matter of just how much leeway Van Wagenen will have to sign those free agents, or to make the trades he wants or draft the players he likes. Jeff and his father Fred have a reputation for meddling and micromanaging, but Van Wagenen welcomes working with them. “They’ve given me full autonomy for building the systems, hiring the people I want to, putting the major league roster together,” he said, but when push comes to shove, who will win out?

Ultimately, though, these issues would have faced any GM, be it Van Wagenen or anyone else. What’s hardest to figure out—what remains a mystery even after all the niceties and compliments—is why the Mets landed on Van Wagenen, and what he brought to the table that no one else could. Wilpon lauded the potential for collaboration and creativity, and Van Wagenen did the same. But what separates his vision from anyone else’s? Wilpon noted how much he liked Van Wagenen’s work ethic and desire to win, and his belief that the Mets as currently constructed could be turned into a winner without a teardown or a long rebuild. Then again, Wilpon said that a dozen other candidates for the job felt the same way, and the majority of them likely wouldn’t have come with the lack of experience or the need to learn on the fly.

The choice of Van Wagenen, then, feels like it’s as much about the relationship between him and the men who own the Mets as anything else. Which isn’t to say that this is doomed to failure or anything like it. No one knows how this will all play out—not the Wilpons, not Van Wagenen, not the press or other teams or anyone else. It’s a step in a different direction, which is remarkable and positive in its own way for a team that never seems to take these kinds of risks. Yet it’s worth wondering all the same whether this is the move that made the most sense—or, if at the end of the day, it’s simply the one that aligned best with what the Wilpons wanted and were most comfortable with, regardless of how well it works.