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The Boston Red Sox introduce Craig Breslow as the new the chief baseball officer of the Boston Red Sox at Fenway Park on Nov. 2. Will he add to the team at the trade deadline? (Staff Photo/Stuart Cahill/Boston Herald)
The Boston Red Sox introduce Craig Breslow as the new the chief baseball officer of the Boston Red Sox at Fenway Park on Nov. 2. Will he add to the team at the trade deadline? (Staff Photo/Stuart Cahill/Boston Herald)
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After the All-Star Game, also known as the Jarren Duran Show, and two interminable days without baseball, the Red Sox are back in business, set to open the second half against the Mookie Betts-less Dodgers in Los Angeles.

Technically speaking, every team blew past the halfway mark about two weeks ago, but the All-Star break is considered the dividing line, so here are my first seven questions of the second half. As always, my inbox awaits your thoughts!

1. What should Sox do at trade deadline?

The July 30 trade deadline is less than two weeks away, and the Red Sox should be gearing up to add. Boston entered the All-Star break 53-42, just four and a half games out of first in the American League East. They hold the third AL Wild Card, are only half a game back from the Minnesota Twins for the second, and three and a half behind the Yankees for the top card.

The Red Sox are in a prime position to kill multiple birds with one stone. Several action items are coming to a head for the organization: they could use a big-league reinforcement or two, and players such as Kyle Teel and Marcelo Mayer look ready for promotions to Triple-A, but the top level of the farm system is a bit overcrowded.

Come December, however, the minor league ranks could be significantly less crowded. Several top prospects will be eligible for the Rule 5 Draft, including 2B Nick Yorke (No. 6), 1B/3B Blaze Jordan (No. 19), RHP Richard Fitts (No. 10) and OF Allan Castro (No. 12). Not only are the Red Sox unable to protect everyone, they also don’t need or even have room for everyone at the big-league level. So rather than wait for another team to steal a prospect for the paltry sum of $100,000, the Sox should make trades while they can. Packaging a few high-level prospects could get them some serious talent and free up space for promotions.

2. What will they do at the deadline?

A very different question than the previous one. But if they kill the momentum this team has by standing pat or selling, they’ll have to explain why.

I can’t fathom any legitimate reason they could possibly have.

3. Can Sox steal the AL East?

Alex Cora has talked about getting “greedy,” aiming for the division crown, rather than one of the three AL Wild Cards, but does that even make sense from a playoff structure standpoint?

In the current postseason format, the team with the lowest win percentage of the three division-winners has to play one of the three Wild Card teams a best-of-five Wild Card round. The Cleveland Guardians own the AL’s best record, so were the season to end on Friday morning, the Seattle Mariners would win the West and still have to play in the Wild Card round.

On the other hand, the AL East battle is so much fiercer than nearly every other division. It’s safe to assume this year’s winning record will be high enough to vault the title-holder directly into the ALDS.

No harm in shooting for the moon, missing, and still landing among the playoff stars.

4. Will Sox develop a true two-way player in Conrad Cason?

Apparently, the organization that sold Babe Ruth away and didn’t make a real bid for Shohei Ohtani is going to attempt a DIY (develop-it-yourself) with Conrad Cason, the two-way player they took in the eighth round of this week’s 2024 MLB Draft.

Gatorade’s Georgia high school player of the year just spent his senior year posting a 0.48 ERA and .085 opponent average, with 99 strikeouts in 43.2 innings, and hitting .364 with three homers, 16 stolen bases, 25 walks, and 28 RBI.

Having just turned 17 three months ago, the righty pitcher and hitter is one of the youngest players drafted this year. He’s also committed to Mississippi State, but if he forgoes college to sign with the Sox, they plan to keep developing both sides of his arsenal.

5. Will Sox become pitching development machine?

Aside from Cason, the Red Sox used 13 of their 19 picks on full-time college pitchers, including second-round pick Payton Tolle. At No. 50 overall, the left-hander is the club’s highest pitching selection since 2017, when they drafted Tanner Houck 24th overall.

Though Red Sox amateur scouting director Devin Pearson said “it was kind of where the board fell,” it’s worth noting that Craig Breslow’s work as the Chicago Cubs’ vice president of pitching was a significant factor in the Red Sox hiring him to be their chief baseball officer last November.

6. How aren’t the Sox a top-10 team?

MLB left the Red Sox, who’ve been one of the best teams in baseball for two months, at No. 11 on this week’s Power Rankings. The Yankees, meanwhile, just managed to take the first two games of their trio with the Orioles, which finally snapped their eight-series losing streak. Yes, I said series. It was also New York’s first time winning back-to-back games since June 11-12.

Somehow, MLB moved the Yankees up a spot, from No. 5 to No. 4. The worst they’ve ranked this season is No. 7, and at one point, they held the top spot. At their worst, the Red Sox were No. 22; they’ve yet to be ranked in the top 10.

David Ortiz says he likes it when people underestimate the Red Sox. And I tend to listen to people who’ve completed one-of-a-kind postseason comebacks and have three World Series rings.

7. Will Yankees know peace again?

On Tuesday, the Red Sox selected D’Angelo Ortiz in the 19th round of the draft.

That’s right, David Ortiz’s son. Born in 2004. Does anyone else hear “Circle Game” playing?

The carousel of time aside, this is an exciting development for one very petty reason. Between the elder Ortiz and Rafael Devers, the Yankees haven’t known peace since 2003. And if the younger Ortiz is anything like his Big Papi and Devers, peace is decades away.

Bonus question: Since David Ortiz works for the Red Sox in a very broad, fluid, eternal capacity, does that technically make him his son’s boss?