4 most difficult decisions the Red Sox could make before spring training

Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) throws a
Oct 28, 2023; Arlington, TX, USA; Texas Rangers starting pitcher Jordan Montgomery (52) throws a / Kevin Jairaj-USA TODAY Sports
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The Boston Red Sox still have some gaping holes in the roster that need fixing. They're the same holes that have existed since the beginning of the offseason, and maybe even earlier.

The Red Sox need an ace, outfield depth and could use a strong, right-handed bat to add some consistent power to the batting order. The bat isn't necessary, but the better pitching and outfield depth should be.

Boston has two sure-fire starting pitchers in Brayan Bello and Lucas Giolito. The rest of the starting rotation is going to be a group of lower-tier starters, such as Tanner Houck and Nick Pivetta, and relievers who will be stretched out.

The Red Sox outfield situation also needs work. Tyler O'Neill is one of the team's newer additions and is a good defender, but his bat doesn't match up with the one the Sox lost in Alex Verdugo's absence. Masataka Yoshida only played 140 games last year, and he played some of them as the designated hitter. A more permanent figure in the outfield is a necessity, and one that could hit for power would be a plus.

4 most difficult decisions the Red Sox could make before spring training

Find a suitor for Kenley Jansen

The Red Sox have been trying to shop closer Kenley Jansen for a few weeks now, and talks have recently intensified. The Dodgers and Phillies have emerged as top candidates for Jansen, and if Boston is insistent on trading him, it should get the job done soon.

On an episode of the "Fenway Rundown" podcast, Boston's new pitching coach, Andrew Bailey, conceded that closers aren't necessary for every roster. He believes closers can only perform as well as they're set up to — if starters and relievers can't keep the Sox in the game, Jansen throwing one shutdown inning at the end may not be worth anybody's time.

By Bailey's logic, the team has more pressing matters to attend to, which should include setting up a competent starting rotation. If dishing Jansen to save money is how the Red Sox need to move to fix the rotation, they should probably do it. Like, now.

The Phillies lost their previous closer, Craig Kimbrel, to the Orioles this offseason. The Dodgers have a fair few relief arms to use on any given day, but a reunion with Jansen could give them the experienced closer that they lack. Boston is running out of time to make a deal.

Red Sox could push to sign an ace before spring training

Starting pitching has been Boston's biggest need for some time, across multiple seasons. The Red Sox lost three starting pitchers this offseason in Chris Sale, James Paxton and Corey Kluber. Instead of adding three starters to the rotation, Boston signed one in Lucas Giolito and is expecting its relievers to pick up the slack.

That plan is not going to work.

Last year's Red Sox rotation only pitched 774.1 innings between all the starters, which is good for the fourth-lowest number in the league. Boston had more true starters last year and it still couldn't even keep its pitchers in the game for the long haul.

The Red Sox have the capability and money to sign any starter they want, but despite their every move being filmed for a Netflix documentary, it seems like they'd rather field a bad team. Jordan Montgomery and Blake Snell are still available and Boston could afford either of them. The Sox have been connected to Montgomery over and over this offseason and Boston has been named as the best suitor for him.

If the Red Sox can manage to trade Jansen and free up the $16 million he would cost them in 2023, they should use the money to go toward signing Montgomery. They need an experienced pitcher who can eat innings and help the reliever-to-starter transition journeys. Montgomery is the best remaining choice and it's time to swallow the stress of investing big money.

Red Sox need to find a new home for Bobby Dalbec

Red Sox slugger Bobby Dalbec admitted to being "kinda sorta" surprised to be going into spring training with Boston this year, and he has the right to be. The Red Sox should've traded him long before now.

Dalbec played over 100 major league games in 2021 and '22 and batted .229/.292/.440. In 2023, the infielder played just 21 games in the majors.

Dalbec's value has decreased since his 2021 season when he played 133 big-league games and hit 25 home runs. The Red Sox should've traded him after 2021 and gotten a better return for a recently successful, younger Dalbec than the one they have now.

The 29-year-old currently sits on the 40-man roster and received a vote of confidence from Alex Cora after his performance in Worcester last year. But with an influx of talented infield prospects coming up through the farm system, keeping Dalbec in the organization doesn't make a ton of sense.

Dalbec is seemingly going to get another chance to prove himself this season as he's headed to spring training with the team. But, if he isn't traded before exhibition games begin, this needs to be his last one go-round with the Sox unless he rediscovers himself this year, a prospect that seems less and less likely with each passing season.

Red Sox outfield and Jarren Duran -- what's going on?

Boston's outfield has been up in the air for the entire offseason. Swapping Verdugo for O'Neill in December may have created more problems than were solved.

O'Neill is a good defender and can take Verdugo's place in right field nicely, but his bat doesn't match the former's production. Jarren Duran is not an outfielder by trade and it shows in his defense. Yoshida's defense leaves something to be desired, too, but he and Duran can consistently get on base and score runs. That's not enough, though. The Red Sox need more, even more than prospects Wilyer Abreu and Ceddanne Rafaela could provide.

Boston's outfield lacks star power and offensive power, as a whole. The team has been connected to Jorge Soler multiple times this offseason, but like the rest of the Red Sox's "interests," no deal has been made. Soler would not solve the Sox's defensive issues in the pastures, but he would bring the offensive production that they're sorely missing from the outfield.

Duran's name has also been brought up in trade conversations, and since spring training is coming, the negotiations are beginning to hold more weight. The Padres have shown interest in the outfielder but they and the Sox have not yet reached a deal. San Diego doesn't have much MLB-ready talent that would make sense to dish in a deal for Duran, so trading him may not improve the outfield, or the rest of the team, at all in the short term.

Boston has also shown interest in a few other outfield candidates, including two who have played with the Red Sox before. Adam Duvall, Tommy Pham, Randal Grichuk and Michael A. Taylor are all available and in need of jobs before spring training starts, and as seasoned vets, they'll all likely get one.

Soler and Duvall seem like the two best candidates so far for restructuring the outfield. Duvall has played for the Sox before and he got off to a hot start last season before injuring his wrist. Soler has the star power Boston's roster usually commands and the strong bat the Red Sox need.

Boston has a lot of options. It needs to decide what it needs most and act on the decision before another team does.

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