Pete Alonso wants a long-term commitment from whichever team signs him. After opting out following the World Series, he’s reportedly targeting a contract of at least seven years. To secure the deal he wants, Alonso is hitting the road with agent Scott Boras, meeting teams face-to-face.

“Pete Alonso is making the 90-minute drive to central Florida on Tuesday, according to sources, to meet in person with interested suitors that include the Red Sox and Orioles. Bring. On. The. Mayhem,” said Jon-Heyman.

He’s set to meet Red Sox chief baseball officer Craig Breslow on Tuesday, and he also has a visit scheduled with the Orioles as he continues evaluating his top suitors.

Even though neither organization commented directly on Alonso, Craig Breslow openly said Boston is still prioritizing a true middle-of-the-order bat, stressing the need for someone who can “change the overall outlook of the offense.” He specifically highlighted power, run production, and the team’s willingness to use pitching depth to address offensive needs, a profile that fits Alonso almost too cleanly.

Baltimore GM Mike Elias echoed that same tone, noting the Orioles are talking to “a whole bunch of hitters” and are simply looking for impact bats who raise the roster’s ceiling. But there’s a real chance he signs elsewhere.

Boston is reportedly one of his top options this time around. Even with Mets owner Steve Cohen’s deep pockets, this update is a big win for the Red Sox. Mets president of baseball operations David Stearns said early in the winter that the team hoped to bring Alonso back.

His durability is unmatched, given that he’s played all 162 games in each of the last two seasons and hasn’t logged fewer than 152 games in any full year of his seven-season career. Of course, aside from the shortened 2020 season.

The Mets, meanwhile, have a history of slow-rolling negotiations with him. What’s still uncertain is whether Pete Alonso will sit down with the Mets as well during this trip. Last offseason, he didn’t meet with them until February. And when he did, the Mets agreed on a two-year, $54 million deal that included an opt-out.

And so far, this week appears to be following the same pattern. David Stearn’s reaction to it all confirms just as much, too.

David Stearns’ take on Pete Alonso’s free agency

David Stearns admitted the Mets have no scheduled meeting with Alonso at the Winter Meetings, despite him being just a short drive away.

“I think Pete knows us really well. I think we know Pete really well,” David Stearns said Monday. He also added that Pete Alonso will “take the time here to perhaps meet with organizations he doesn’t know quite as well.”

“Pete has demonstrated that he’s one of the best offensive players in baseball, and he’s performed at a high level for us. That would be a priority for any team. It certainly is for us.” Stearns added. But it only strengthens the belief that other teams may get a head start.

Until now, this is the clearest picture we’ve had of Pete Alonso’s free agency so far.

That urgency also aligns with how Alonso’s market is shaping up. Boston Globe reporter Pete Abraham wrote that Alonso views the Red Sox as one of his top fits, helped by his familiarity with the region and the fact that his wife, Haley, is a Boston-area native. Abraham also noted projections of a four- or five-year contract near $28 million per year, noticeably shorter and lighter than previous estimates that ranged from $150–$210 million.

For all we know, he might make his decision just days after meeting with Craig Breslow. His market stretched into late January last year, and that’s not ideal. So, he may simply want to get things settled quickly this time.

A similar situation played out during Aaron Judge’s 2022 free agency, when he took an in-person meeting with the San Francisco Giants while also receiving a massive late push from the Padres, who reportedly offered him $400 million. Judge’s willingness to explore the market and the leverage it created mirrors Alonso’s approach now. Face-to-face visits and competitive bidding often force teams to become more aggressive, which is precisely what Alonso aims to achieve.

It looks like the New York Mets aren’t planning to meet with Pete Alonso at the Winter Meetings this week. The five-time All-Star, who just turned 31 on Sunday, actually puts up only a couple of hours from the Florida hotel hosting the event. And even then, as a second-time free agent, he likely doesn’t have a scheduled sit-down with his former team.

When David Stearns was asked about where things stand with Pete Alonso now, he stayed loyal to his “no public negotiations” approach. Still, he certainly gave some insight into where he believes Alonso fits in this year’s market.