One last heptad for the long and winding road that was 2025 …

1. Will the Red Sox spend a dollar in free agency before the new year?

As of 7 p.m. Saturday, the Red Sox and Colorado Rockies were the only clubs without a single dollar spent in free agency this offseason.

Quite the pair of peas in a pod: one of the biggest-market teams in the world and a perennial also-ran.

The ‘Why’ – or rather, ‘Why not’ – of Red Sox spending has been discussed and dissected to a particle level: they were aggressive but outbid; they’ve made several trades; they were over the luxury tax this year; they don’t like long-term deals; they feel confident with the roster they have. And so on and so forth.

None of these reasons – or excuses – really matter. This club has needs and there are free agents who can fill them. If the Red Sox want to be taken seriously as a big-market franchise again – and field a better team – they will make something happen.

2. Do the Red Sox’s chances of re-signing Alex Bregman improve or worsen as the days go by?

The Red Sox played the waiting game with Bregman last offseason, and he finally fell into their lap one day after pitchers and catchers reported to spring training.

After seeing how Bregman contributed to the team this season, both on the field and in the clubhouse, I was cautiously optimistic the Red Sox would be aggressive in retaining him. Especially because Bregman made it clear how much he enjoyed not only being part of the Red Sox, but making a home in Boston with his family.

Instead, Bregman is drawing even more interest than last year, and the Red Sox somehow seem even more hesitant to spend.

Fool me twice, shame on me, I guess.

3. Are the Sox really going to go into a season with four starting outfielders?

Until the MLB Winter Meetings earlier this month, it seemed a foregone conclusion that the Red Sox would move either Wilyer Abreu, Jarren Duran, or Ceddanne Rafaela, or find another way of ensuring an everyday defensive role for Roman Anthony.

Then again, when Abreu and Anthony suffered lengthy injuries late in the summer, the Red Sox were grateful to have a surplus of outfielders.

4. What’s going to happen to Masataka Yoshida?

The current Red Sox roster isn’t conducive to an everyday designated hitter, but with the aforementioned quartet of outfielders, that would be Yoshida’s likely role.

If the last two seasons are any indication, it will only hamstring the ‘26 Red Sox.

Yoshida served as the DH in ‘24 because a shoulder injury prevented him from playing a defensive position. When Rafael Devers and Tyler O’Neill needed to DH after their April outfield collision, Yoshida was sidelined for several games. It happened again and again as other teammates returned from injuries and borrowed Yoshida’s job.

Forcing Rafael Devers into the same role last season created a similar logjam. It blocked Yoshida and, for the week between Anthony’s debut and the Devers trade, made it difficult to fit the rookie star and the rest of the outfielders into the lineup.

What would be different this year? If Willson Contreras is the primary first baseman and Yoshida the DH, where does that leave Triston Casas when he returns from his knee injury?

5. What can Roman Anthony do over a full MLB season?

Hopefully we’re about to find out.

Extrapolating from Anthony’s truncated rookie season, it’s thrilling to think about the impact he can make over a 162-game campaign. Between his June 9 debut and season-ending oblique strain on Sept. 2, he hit .292 with a .859 OPS in 71 games. From June 16 – when he played the seventh game of his career and hit his first big-league home run – until the end, he hit .308, got on base at a .412 clip and slugged .488.

The Red Sox probably defeat the Yankees in the Wild Card series if Anthony is healthy.

What’s next for the newest face of the Red Sox? Anthony’s first career multi-homer game? First All-Star selection? First postseason?

6. Will the Red Sox trade Brayan Bello?

According to The Athletic, the Red Sox have “quietly shopped” Brayan Bello, their 26-year-old homegrown right-hander.

The Red Sox signed Pedro Martinez’s protege to a team-friendly extension through ‘29 in March ‘24, with a club option for the ‘30 season.

While there’s certainly depth in the Red Sox starting pitching ranks, much of it is unproven in the Boston market. Sonny Gray and Johan Oviedo figure to make the rotation out of spring training, but both were acquired this offseason. Patrick Sandoval missed his entire first season with the club last year as he rehabbed from Tommy John surgery. Kutter Crawford is expected to have a normal spring training after missing all of last year due to knee and wrist injuries, but his track record is far from spectacular. Lefty rookies Payton Tolle and Connelly Early have seven career MLB regular-season starts between them.

Bello showed significant improvement this year, posting a career-best 3.35 ERA over 29 games (28 starts). However, his 4.19 FIP, the metric which measures a pitcher’s effectiveness regardless of his team’s defense, was identical to the previous season, which suggests he benefitted from better fielding.

Yet despite the inconsistent, sometimes underwhelming beginnings of Bello’s career, he has been more durable than most Red Sox starters in recent history. He tossed a career-high 166.2 innings this year, his third consecutive season with at least 157 innings pitched; the last Red Sox pitchers to reach 157 innings at least three times, consecutively or otherwise, were Rick Porcello and Clay Buchholz, who last pitched for the club in ‘19 and ‘14, respectively.

Availability is always the most important metric in my book.

7. What was your favorite Red Sox moment of 2025?

For me, it’s hard to top getting to witness Ceddanne Rafaela’s playoff berth-clinching walk-off and the ensuing clubhouse celebrations. The October run was short, but a tremendous honor to cover.

Email me and let me know your favorites. Happy new year!