As early as Sunday, and no later than Monday -- depending on the outcome of Game 6 of the World Series - baseball free agency begins and you have to go back a while to find a time in which that seemed more pivotal for the Red Sox as a franchise.
In fact, even before the Red Sox pursue outside help on the market, there's the not-insignificant matter of whether they can retain their own free agent -- shortstop Xander Bogaerts, who will undoubtedly opt-out of his contract in a matter of days. If the Red Sox can't or won't re-sign Bogaerts, there's no shortage of potential replacements at the position. Like last winter, this offseason's best positional crop is shortstop, with three other All-Star options should Bogaerts land elsewhere.
Then there's the matter of Rafael Devers, who has another year to go before qualifying for free agency. Typically, players with additional control years remaining end up getting extended after the first of the year, when much of the remainder of the team's to-do list has been checked off. But given the importance of Devers to the organization, the club could treat contract talks with more of a sense of urgency this winter. Or not.
For a team that finished last in its division, with a losing record, the Sox' needs are plentiful. They need upgrades to their rotation, their bullpen, a corner outfielder and perhaps catching help.
Here's a look at those needs, along with some potential solutions and guesstimated pricetags.
STARTING PITCHING: This area is top heavy with some intriguing stars, led by Justin Verlander and Jacob deGrom, two of the top five starters in the game when healthy. But the 'when healthy' part is the operative phrase here. Verlander will be 40 before the start of spring training, and though he pitched brilliantly in 2022 and is likely to win the A.L. Cy Young Award, he would be an enormously expensive and risky investment.
The same goes for Jacob deGrom, who can be otherworldly, but has made just 26 starts combined in the last two years thanks to a variety of injury concerns, not the least of which is his invaluable right shoulder.
A more sensible target would be lefty Carlos Rodon, who was 14-8 with a 2.88 ERA for the San Francisco Giants last year while leading all of baseball in strikeouts-per-nine innings (12.0). Rodon, 30, has his own injury concerns, but has been healthy in each of his last two seasons. He'll undoubtedly attract a qualifying offer from the Giants, but that shouldn't dissuade the Red Sox.
Rodon could serve as the Red Sox' link between aging, fragile former ace Chris Sale and potential future top-of-the-rotation star Brayan Bello. Expect that Rodon will likely command, at minimum, the kind of deal given to another former Giant -- Kevin Gausman, who last winter landed a five-year, $110 million deal with Toronto. Perhaps Rodon could command more. Let's call it: five years, $125 million.
That's not cheap, but then, quality starting pitching never is.
Even if the Sox land Rodon, that won't be sufficient. They'll need at least one other experienced starter to add to a group that includes Sale, Rodon, Bello and Nick Pivetta.
Two of their own veteran righthanders -- Nate Eovaldi and Michael Wacha -- are free agents, too. While Eovaldi was an above-average starter for them over the last four years, his durability remains a question mark. He'll be 33 in February and the fact that he spent time on the IL in three of the last four seasons represents a huge red flag. I would expect the Sox will give him the QO ($19.65 million), which he'll reject, giving the Sox an extra pick after the fourth round.
It might be worth taking the same approach to Wacha, who was the team's best starter in 2022 -- admittedly, a low bar to clear -- at 11-2, 3.22. Wacha, too, has dealt with injuries and like every other pitcher age 30 or older, and carries considerable risk. Though it would be an overpay, I would give Wacha the QO, too, with the reasonable expectation that he will turn it down in search of the security of a long-term deal. And if he does accept, then a one-year deal carries far less peril for the club.
Should the Sox need other targets, there are no shortage of middle-to-back-end starters, including Jameson Taillon, Taijuan Wallker, and Chris Bassitt. But each of those pitchers are, again, 30 or older and will command commitments of at least three years if not four, with an AAV between $16-$20 million. That's not an efficient way to find back-end pitching.
A more intriguing choice would be Japanese righthander Kodai Senga. Senga hits triple digits with his fastball and his split-finger is devastating. And at 29, he might be a more worthwhile multi-year investment. Expectations are he'll sign for three or four years, with an AAV somewhere between $18-$20 million.
in the event the Sox have plans to shift Garrett Whitlock to the rotation, they could round out their rotation with a short-term deal for a back-end free agent. That group includes the likes of Zack Eflin, Jordan Lyles, and their own Rich Hill.
OUTFIELD: With Kiké Hernandez under control and returning to handle center, and Alex Verdugo likely heading back to left field, the Sox have two-thirds of their outfield set. What they need is someone who could play right field.
In an admittedly thin outfield class, Michael Conforto represents an intriguing option. Conforto missed all of last year after undergoing shoulder surgery, but is said to be healthy again. He's a lefty bat when the Sox would probably prefer a righthanded one, but that's a quibble. Conforto is a slightly above average right fielder who gets on base (.356 career OBP) and from 2017-2019 averaged almost 30 homers per season.
After missing all of last year, Conforto isn't in the position to command a long-term commitment. Something in the neighborhood of two years, $30 million -- with perhaps an option year, or an opt-out after the year, would likely get it done.
Another possibility, with even less certainty attached, is Mitch Haniger, who has also dealt with injuries for much of the last handful of seasons. In fact, he's played more than 100 games in a season just once in the last four seasons. In 2021, Haniger hit 39 homers and knocked in 100 runs with an .804 OPS. So the ability's there.
Haniger is an adequate defender, but doesn't get on base much anymore (.308 OBP this past season). If the Sox could do a deal with lots of incentives, he might not be a bad option with a base, say, of $8-10 million.
Another possibility is Joey Gallo. Gallo is good defender with great power potential. He once averaged 40 homers over three full-length seasons (from 2018-2021). But the power has dipped in recent years, and his inability to deal with the pressure and expectations that come with playing in New York does not exactly fill you with confidence about his ability to handle Boston.
Finally, for a team looking to make more consistent contact and put the ball in play more, Gallo's 41.6 strikeout rate is cartoonishly high and would seem to serve as the ultimate disqualifier.
CATCHER: It's unclear exactly what Chaim Bloom meant when he said after the season concluded he would "explore additions'' to the catching duo of Reese McGuire and Connor Wong.
What, precisely, did that mean? Will the Sox seek a No 1 catcher to handle the bulk of the games? They tried doing so last year when they tried to acquire Jacob Stallings from Pittsburgh. Or is Bloom talking about someone who could come in and compete with McGuire and Wong, and serve to push them? Hard to say.
I can't see the Red Sox becoming bidders for the top catcher in this class, Willson Contreras. Given the other holes they have to fill -- both outside the organization and with the left side of their own infield -- it's impossible to imagine them spending the $80-$100 million or more Contreras will command.
If there's one free agent catcher the Sox might splurge a bit on, it's Mike Zunino, who's familiar to Bloom from their time together in Tampa Bay. Zunino offers plus power (33 homers in 2021) and plus arm strength. Some drawbacks -- Zunino led the league in passed balls in both 2020 and 2021 and, of course, his frightening strikeout rate (34.7% in his career).
Zunino is coming off a year in which he underwent season-ending thoracic outlet surgery on his left (non-throwing) shoulder, which will make him more affordable on a short-term deal.
One baseball executive, in the aftermath of last August's trade deadline, said he would not be surprised to see the Sox reunite with Christian Vazquez, whom they unloaded in August to Houston for two prospects. Vazquez loved playing in Boston and would likely be interested in returning. But it seemed that some in the organization had soured on him and the fact that the team was willing to unload its top catcher while still nominally in the playoff hunt speaks volumes.
I think it's far more likely the Sox continue to search out trade possibilities (Oakland's Sean Murphy would be a huge upgrade, but also enormously expensive in terms of prospect cost) and that ultimately, they sign a veteran to provide additional depth.
One potential target: Omar Narvaez, who has seen his offensive production dip in recent seasons, but is still considered a strong receiver.
BULLPEN: This is a difficult area to assess because it's unclear what the Red Sox plan to do with Whitlock and Tanner Houck. If they keep both in the bullpen, the team's relief corps will be nearly fully assembled. A pen consisting of Whitlock, Houck, Matt Barnes, John Schreiber and a group that includes young promising arms like Zack Kelly and Franklin German would be nearly complete, needing only a lefty and another experienced high-leverage arm.
If, however, the plan calls for one or the other to transition into the rotation, that would create another hole.
Unless the Red Sox decide to give Barnes another chance to close -- he had a 1.59 ERA from August through the end of the season -- the Sox could use someone with closing experience.
It would seem unlikely that the Sox would spend big to fill that role. Kenley Jansen is a free agent, but will command a salary in the neighborhood of $15 million, and that kind of outlay for someone who might throw 70 innings seems to run counter to team philosophy. That goes double for Edwin Diaz, who, coming off a career-best season with the Mets, will almost certainly become the highest-paid closer in history.
Among particularly analytical organizations like the Sox, allocating that amount of money for a closer is rare.
It's more likely that the Sox find a veteran reliever who has late inning experience, and try him in the ninth inning.
Houston's Rafael Montero, who blossomed after being dealt from Seattle to the Astros, would be a logical target. Another option could be Chad Green, who underwent Tommy John surgery last May, but could be ready by mid-season. A deal for Green, of course, would feature a lower base guarantee and incentives, and likely, an option for 2024.
Regarding the need for a lefty, the Sox could do worse than re-sign their own free agent Matt Strahm, who was effective them against both lefties and righties. Strahm's interest in becoming a starter, which he spoke of in September, could complicate matters.
DESIGNATED HITTER: For the first time since 2017, it would appear this role will not be filled by J.D. Martinez. Martinez is a free agent whose 2022 season signaled a downturn in performance (his .790 OPS was his lowest in a full season since 2013).
If the Sox wish to have another veteran slugger who could match Martinez's past production and serve as a hitting savant for younger players, they could go with Jose Abreu. Abreu's time with the Chicago White Sox has seemingly come to an end and he could be a nice two-year solution for the Sox.
Whether the Red Sox want to commit somewhere between $15-$20 million annually to a 35-year-old slugger is another question altogether. Abreu had a better season than Martinez, but his dropoff in homers (from 30 to 15) is similarly alarming.
From within, the Sox could fill the DH vacancy with a platoon of Bobby Dalbec and Franchy Cordero, two hitters with enormous power potential, but difficulty achieving consistent contact.
Or, the Sox could follow the industry-wise trend and use the DH spot as a way of giving a number of their best offensive performers (Devers, Trevor Story, Trison Casas, and if he remains, Bogaerts) some respite from defensive responsibilities and cycle them through the DH role.