New year, new questions!

1. Would Vladimir Guerrero Jr. be a fit for the Red Sox?

Alex Bregman’s asking price was too high for Houston, and it may be too high for Boston, too.

The Astros offered their longtime third baseman six years, $156 million before pivoting when negotiations stalled. The Sox, desperate for a righty bat to balance out their lineup, don’t want to be tied to Bregman, who turns 31 on March 30, for seven years. Nor do they want to commit $200 million to him. (Though they’ve been reluctant to commit as much as $100 million to any free agent in recent years.)

The impending free agency of four-time All-Star Guerrero Jr. could be another factor.

“If Guerrero doesn’t receive an extension by spring training, he’ll test free agency,” wrote USA Today’s Bob Nightengale on Tuesday. “If Guerrero doesn’t return to the Blue Jays, he would love to be with the Red Sox, friends say, which may be why the Red Sox are hesitant in their pursuit of Bregman.”

Statistically, the Toronto slugger is a strong fit for Boston. In 46 career games at Fenway Park, he’s hit .356 with a 1.054 OPS and 64 hits, including 18 doubles and 10 home runs, 44 RBI, 25 walks, and 32 strikeouts. According to Stathead, he’s is one of eight active major leaguers to average at least .300 over a minimum of 40 games at Fenway, but the only one with an OPS of 1.000 or higher.

Guerrero is reportedly seeking a contract over $450 million. In a recent appearance on the Abriendo Sports podcast, Guerrero said Toronto offered him seven years, $150 million after the ‘21 season, then made no formal offers in ‘22 or ‘23. Though he declined to reveal the Jays’ most recent offer, he confirmed it was in the vicinity of the $340 million reported by MLB player-turned-insider Carlos Baerga, who’s broken several big signings in recent offseasons, including Rafael Devers’ Red Sox extension two years ago. Nightengale wrote that the slugger and his team are “at least $100 million apart” in their ongoing negotiations.

The Red Sox could trade Casas at the deadline or next offseason to open first base for Guerrero. Chief baseball officer Craig Breslow maintains they’re not actively shopping Casas, but they’ve already listened to offers for him this offseason.

2. Could Guerrero Jr. play third for the Sox?

Guerrero came up through the minors on the opposite corner and debuted there in ‘19. In the Abriendo interview, he revealed that he was originally moved from third to first as punishment for showing up overweight when baseball reconvened in July 2020 after a months-long hiatus due to the COVID-19 pandemic.

“Our main message was ‘Become a Gold Glove first baseman and then we’ll move you to third, see how it goes,” then-Blue Jays manager Charlie Montoyo told reporters at spring training in ‘21, when Guerrero reported to camp having dropped 42 pounds.

Guerrero won the Gold Glove at first in ’22, then made lone appearances at third in ‘21 and in ‘22. He played third 12 times last year (11 starts), his defensive versatility garnering praise from Jays manager John Schneider.

3. Can Nolan Arenado still hit lefties?

After going 17-26 against left-handed starters last season and losing Tyler O’Neill in free agency, the Red Sox desperately need a righty bat to balance out their lineup.

Theoretically, St. Louis Cardinals third baseman Nolan Arenado fits the bill, but he didn’t hit lefties well last year, either; he averaged .235 with a .646 OPS against them, compared to .284 with a .743 OPS against righties. The numbers were closer against starting pitchers but not exactly impressive: .279 with a .720 OPS against southpaw starters, .269 with a .719 OPS against righties.

It’s a harsh flip-flop from the hitter he was between his ‘13 debut and the end of the ‘23 season, averaging .303 with a .956 OPS against lefties, compared to a .281 average and .842 OPS against righties. Arenado’s power has also plummeted over the last three seasons; after averaging 39 home runs per 162 games between 2015-22, he hit 26 homers in ’23 (144 games) and 16 in ’24 (152 games).

An Arenado acquisition would also be complicated for several reasons. He’s reportedly willing to waive his no-trade clause for Boston, but the Sox would need to make significant rearrangements to accommodate him; Devers doesn’t want to cede third base, and Masataka Yoshida currently occupies the designated hitter spot.

And if Arenado can’t hit lefties anymore, is it even worth it?

4. Would Devers be able to play first base?

There’s been talk of moving Devers off third pretty much since he arrived in the Majors in the summer of ‘17, but it’s looking like a real possibility now that the Red Sox have been linked to Bregman and Arenado.

Devers will likely end up as the DH later in his career, but he just turned 27 and is only one year into his franchise-record 10-year, $313.5 million extension. He also takes immense pride in playing third and has worked hard to improve. In ‘24, he often looked like a Gold Glove-caliber third baseman, and manager Alex Cora reiterated throughout the season that the stats didn’t paint an accurate picture of Devers’ defense.

The Red Sox could trade Casas or Yoshida and move Devers into one of their roles, but there’s no guarantee that forcing him to switch positions wouldn’t backfire. It’s not uncommon for players to struggle in one facet of their game and see that bleed into the others; when Andrew Benintendi struggled at the plate in ‘19, his defense and base-running began to falter as well.

If Devers is unhappy with a move it could impact his offense, and that would be far more catastrophic for the Sox than the occasional botched play at third.

Not to mention a waste of the largest contract in franchise history.

5. Why are the Sox interested in Pete Alonso?

The longtime New York Mets first baseman may be a younger, more affordable righty addition than Arenado, but some of his offensive numbers are already trending downward and he’s not an elite defender.

It makes sense the Sox want to explore all avenues of improvement, but it’s somewhat baffling how much they’re looking at outside options for first base when they have the young, very affordable, potential-laden Casas on the roster.

6. Why would Chris Martin turn down a more lucrative offer from the Red Sox to sign with the Rangers?

The Red Sox made Martin a more lucrative offer than the one-year deal he took from the Rangers this week, but sometimes it’s not about the money. Throughout last season, Martin debated retiring at year’s end or giving it another year. In the fall, he said he was leaning toward the latter, especially if he could play closer to home. In that regard, the Texas native and his new team are a perfect fit.

However, Martin’s departure increases the Red Sox’s relief needs significantly. Imploding on a near-nightly basis in the second half, the bullpen was a driving force in their collapse down the stretch. The good news is the relief market is still full of talent, most notably Tanner Scott.

7. Why isn’t Roki Sasaki interested in the Sox?

The Red Sox reportedly weren’t among the teams invited to in-person interviews with Japanese pitching phenom Roki Sasaki and his agents. Given their long track record of success with Japanese players and the presence of Sasaki’s Team Japan teammate Masataka Yoshida, it’s somewhat surprising.