For Red Sox, what would make for a successful winter meeting?

SAN DIEGO — There were two mid-afternoon flights from Boston to San Diego on Sunday, and each one had Red Sox bigwigs onboard making their way to the Winter Meetings. One team president. A chief baseball officer. A handful of vice presidents and assistant general managers. Even the clubhouse attendants. They all had plenty to do once they landed.

Baseball’s offseason doesn’t come with a clock, but it does have a few helpful guideposts, and this gathering is a big one. The Winter Meetings are an opportunity to meet in person to negotiate trades and finalize deals. The offseason’s a month old at this point. Dominoes are starting to fall. The market is taking shape. It’s not necessarily late, but it’s certainly not early.

It’s time to do something. Especially for a team with a lot of money to spend and massive holes to fill.

So far, the Red Sox have addressed the bullpen, and little else. They’ve officially signed lefty Joely Rodriguezand they should finalize a two-year deal with righty Chris Martin any day now. That’s helpful — especially Martin — but it’s small potatoes compared to the work that needs to be done at shortstop, in the outfield, at designated hitter and in the rotation. The Red Sox tried to sign both Jose Abreu other Zach Eflin and missed out on both.

So, what does a successful winter meeting look like?

To some extent, that depends on everyone else. If the entire industry does nothing these next three days, the Red Sox can keep kicking the can down the road, but that won’t help anyone. Ideally there’s action, with the Red Sox in the thick of it. A successful winter meeting looks something like this.

1. Xander Bogaerts, obviously

There are four high-end shortstops available, and recent reports seem to have focused on two of them: Bogaerts and Trea Turner. That might not mean anything, but there appears to be a little more smoke around those two. The Phillies and Padres are getting a lot of digital inc in this arena, but the Red Sox loom as an obviously interested party. There was a brief suggestion that they might be out of the running, but sources from all corners denied it.

So, an ideal Winter Meeting surely starts with Bogaerts making a decision to stay. The team has been steadfast in calling him their offseason priority. He’s spent a month exploring the open market and surely has a feel for the going rate, which means the Red Sox should understand — or know soon — exactly how much it’s going to take to keep him.

If they’re not going to keep him, the Red Sox need to recognize and accept that sooner rather than later so that they can move on before all of the Plan B’s are taken.

2. At least one starting pitcher

The rotation market was at a standstill Jacob de Grom signed for — wait, what’s that? Five years?

OK, so the rotation market has roared to life, and it’s a monster. The Red Sox were never expected to be in the market for deGrom or Justin Verlander, but that deGrom contract, followed by Verlander’s shorter-term, two-year, $86 million deal with the meads, have set a high ceiling. And multiple sources have said the Red Sox are not going after a bunch of No. 4s and 5s this offseason. They want a couple of No. 2s — give or take — who push their existing starters into more appropriate roles (Chris Sale at No. 3, Garret Whitlock at No. 4, Brayan Bello or James Paxton or Nick Pivetta at No. 5 — something like that). To make it happen, the Red Sox don’t need a Cy Young winner, but they don’t need Garrett Richards, either.

We know they nearly signed Zach Eflin — is he a top half of the rotation starter? — and made a qualifying offer to Nathan Eovaldi. Multiple sources have said they are eyeing Kodai Senga, but apparently that applies to everyone. Chris Bassitt is also out there. Trade speculation has swirled around Shane Bieber and Corbin Burnes.

If deGrom was the domino to send the others tumbling, the Red Sox will need to make a move before they’ve all gone down.

3. New right-handed hitter

As if their shortstop and three-fifths of their rotation weren’t enough, the Red Sox also lost designated hitter JD Martinez to free agency this winter. Among their top returning hitters are three lefties: Rafael Devers, Alex Verdugo other Triston Casas. They still have Trevor story other Kike Hernandez, but the Red Sox clearly need a right-handed bat. They tried to get José Abreu, and it didn’t work.

So, they need someone else.

Reports have linked the Red Sox to right-fielder Mitch Haniger — have we mentioned the Sox could use a corner outfielder? — and the free agent market really doesn’t have a ton of alternatives from the right side. There’s Martinez, of course — and Aaron Judge — but Brandon Nimmo, Matt Carpenter, Joey Gallo, Andrew Benintendi, Michael Conforto and Michael Brantley are all free agent lefties. The other rights include Willson Contreras, Justin Turner, Trey ManciniJosh Bell (a switch-hitter) and Nelson Cruz (who’s 42 and slugged just .337 last year).

Again, this isn’t a market deep enough to be left with the last man standing.

4.Move some spare parts


Could a Bryan Reynolds deal be a real possibility? (Charles LeClaire / USA TODAY)

News broke this weekend that Bryan Reynolds wants out of Pittsburgh. It’s a wonderful city, but it’s hard to blame him. It’s also, presumably, hard to get him. The Red Sox won’t be able to give the pirates a bunch of extra guys and get back a player like that with three years of remaining team control. They can try, and probably should try, but if Reynolds is traded, it’s going to be a blockbuster. The Red Sox might not have the stomach for it.

But the Red Sox might be able to help themselves by doing something smaller. Despite all of their holes, their current roster has a handful of young-ish players who don’t necessarily fit their needs but might have value elsewhere.

If the Red Sox could put together some combination of Jarren Duran, Bobby Dalbec, JoshTaylor, Jeter Downs, Darwinzon Hernandez and one or two of their somewhat redundant Triple-A starters — plus Eric Hosmertoo, if it works — they just might have a package capable of landing a relief pitcher or a corner outfielder.

Frankly, their improved farm system might also be enough to make a more substantial trade (even a Reynolds-sized trade, if they want to go big enough to include the Ceddanne Rafaela-Miguel Bleis-Nick Yorke tier of prospects, just under the Casas-Bello-Marcelo Mayer level).

Point is, it’s not only the Red Sox who flew into San Diego on Sunday night. Top brass from all 30 teams will be there, and they’ll be ready to talk trades. The Red Sox have the inventory — and the incentive — to make a move, whether big, small or somewhere in between.

5. Something less than perfect everywhere else

A baseball executive made an off-hand comment late last week. He said the American League East could be the best it’s ever been this season. the Rays have a tone of pitching. the Blue Jays clearly are contenders. the Orioles have gotten much, much better. And the Yanks are the Yankees. It’s not one or two teams anymore. The division is deep, and it’s still heavy at the top.

So a best-case Winter Meetings for the Red Sox has to include a less-than-ideal Winter Meetings for the teams they’re trying to beat. That means Aaron Judge going home to San Francisco, Carlos Rodón going to Queens (not the Bronx), and the Big 3 non-Bogaerts shortstops landing in San Diego, Philadelphia and Atlanta. One early move has already gone in their favor, with newly-minted Met Justin Verlander trying to win an NL Cy Young for once.

And whatever starting pitcher the Red Sox decide to target next? Make sure the Rays aren’t allowed to take him away just as the lawyers are typing up the contract.

The Red Sox haven’t done much yet, but that’s true of almost everyone. The Red Sox have the farm system and the spending power to be as busy as anyone this week. In their best-case scenario, they do just that.

(Top photo of Haniger: Jim McIsaac / Getty Images)

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