Red Sox mailbag: What pitchers could Sox target in MLB Draft?

We’ve reached the season’s one-third mark, and at this point we have a good idea of who is a contender and who is a pretender. The New York Yankees, Philadelphia Phillies and Los Angeles Dodgers rank among the league’s elite, the Cleveland Guardians and Milwaukee Brewers have exceeded expectations and clubs like the Chicago White Sox and Colorado Rockies are looking at a long slog of a last-place summer.

Then there’s the Red Sox, who find themselves right in the middle hovering around .500.

Now that we’re two months in we asked readers for their thoughts, and almost across the board fans are looking to the future for a sense of what the Red Sox can do to break this cycle of mediocrity. In this week’s mailbag we cover the MLB Draft, potential trade scenarios and who could be on the move if the club decides to sell more aggressively ahead of the July 30 trade deadline.

Who are some pitchers the Red Sox could be looking at in the draft? — Adam A.

It’s probably a little too early to say with certainty who Boston’s possible draft targets could be, and we’ll obviously dive much deeper into this as the draft gets closer, but there are a handful of arms we can reasonably presume would be potential fits when the Red Sox pick at No. 12 overall.

The top pitchers in the draft include Arkansas’s Hagen Smith, Wake Forest’s Chase Burns and Florida two-way star Jac Caglianone, all of whom will likely be off the board by the time the Red Sox pick. One arm in a similar stratosphere who could still be up for grabs is East Carolina’s Trey Yesavage, who has enjoyed a career year going 11-1 with a 2.09 ERA and 139 strikeouts over 86 innings entering the postseason. The 6-foot-4, 225-pound right-hander has a big frame and boasts an effective four-pitch mix that includes a mid-90s fastball along with a plus slider and changeup. If Boston could get him he’d likely become the organization’s top pitching prospect right out of the gate.

Others viewed as potential first-round talents include Iowa’s Brody Brecht, Vanderbilt’s Bryce Cunningham and high school arms like William Schmidt, Braylon Doughty and Cam Caminiti, cousin of the late MLB All-Star Ken Caminiti. Maybe the most intriguing from a local perspective, however, is Duke’s Jonathan Santucci. A former Phillips Andover star from Leominster, the left-hander earned First-Team All-ACC honors with the Blue Devils this spring and boasts a mid-90s fastball along with a strong slider. He’s generally being pegged as a late first-round or early second-round pick in the mock drafts, so he might not be an ideal fit at No. 12, but it’s still so early in the process that things could look a lot different two months from now after the College World Series and MLB Draft Combine are finished.

If Rafaela continues to struggle this badly offensively, do they keep playing him all year? Or do they eventually option him? — @YirmiyahuLaw

Ceddanne Rafaela isn’t going anywhere. The offense is still a work in progress, but it’s not an exaggeration to say his defense at both shortstop and center field has helped kept the team afloat. It seems like every night he makes another outrageous catch in center field, and his ability to play shortstop at a high level has not only allowed the club to maximize its plethora of outfielders, but also brought needed stability after Trevor Story went down.

You can live with a guy hitting below the Mendoza line if he’s adding value like that defensively.

Obviously the Red Sox want to see improvement offensively, but at this point it’s probably best he gets his growing pains out of the way at the big league level. His high chase rate remains an issue and to this point he’s struggled to make solid contact or get on-base consistently, but the transition from Triple-A to the majors is a difficult one and plenty of highly touted prospects struggle initially. Think back to last year when Triston Casas was batting .193 at the end of May, or how last month Orioles infielder Jackson Holliday, baseball’s No. 1 prospect, went 2 for 34 with 18 strikeouts in 10 games before being sent back down for more seasoning.

The Red Sox are going to be patient with Rafaela, and having already awarded him an eight-year, $50 million contract extension, they’re invested in his success. And even if he remains a black hole at the bottom of the lineup through the rest of his rookie year, there’s worse things than having a Gold Glove center fielder batting ninth.

Also, it’s worth noting this question was submitted before Rafaela hit two home runs on Friday night. As of this writing he’s now batting .348 over the last week, his 33 RBI lead all MLB rookies and his seven homers are tied for second. Obviously we’ll see if he can keep it up, but that’s certainly something.

Is there any reason not to tear this thing down? Can Craig Breslow do what Chaim Bloom couldn’t? — @KRGordz

I don’t think the Red Sox are at a stage where a full tear-down is necessary, but I absolutely can see Breslow selling more aggressively than Bloom did over the past few summers to help bring more young pitching talent into the organization. So let’s say we get to mid-July and the Red Sox are clearly not going anywhere. What would a selloff look like?

I think Kenley Jansen is the most obvious trade chip, and based on recent rumors and reporting it sounds like he’s as good as gone. The club likely isn’t going to re-sign him in free agency, so it would be prudent to deal him to a contender like the Dodgers and get something of value in return. The Red Sox could also deal Chris Martin, a veteran reliever who is also in the final year of his contract, for similar reasons.

Other pending free agents who could be coveted on the trade market include outfielder Tyler O’Neill and starter Nick Pivetta, the latter of whom could command a huge haul if he stays healthy and keeps pitching at a high level. First basemen Dominic Smith or Garrett Cooper could be unloaded once Triston Casas returns to the lineup, and right-handers Chase Anderson and Brad Keller are also pending free agents, though they’re probably worth keeping around as inning-eaters for the second half.

Those would be the most likely trade candidates, but what about something a little more ambitious? If Breslow really wanted to reset the deck, one way he could do it would be to try and unload Masataka Yoshida.

When healthy the Japanese outfielder has proven he can hit at a big league level, but he’s no longer a good fit for the Red Sox roster and has become relegated to full-time designated hitter duty. The problem is Yoshida will be owed another $54 million over the next three years after this season, and between that and the longstanding concerns about his durability, Yoshida probably won’t command much interest on his own.

So if Yoshida were dealt, it would probably be part of a larger deal that includes someone like Pivetta. We’ve seen trades like that before: Carl Crawford and Josh Beckett were each packaged with Adrian Gonzalez in 2012, and David Price was included as part of the Mookie Betts trade.

Personally I don’t think the Red Sox need to trade Yoshida, he’s been hurt most of this season and frankly the club needs his bat back in the lineup. But I can also see why Breslow might find the idea appealing, so it wouldn’t be crazy to imagine a deal coming together.

In the event of a Kenley Jansen trade at the deadline, who is the Red Sox closer of the future? Is Rule 5 pick Justin Slaten the next man up? — @MagicOriole

It’s Liam Hendriks. Before his career (and life) was thrown into disarray by his cancer diagnosis and subsequent Tommy John surgery, Hendriks had been one of the best closers in baseball for four years. I imagine the Red Sox expected he would eventually slot into that role when they signed him, and the timeline actually could line up perfectly if the club ultimately deals Jansen before the trade deadline.

Hendriks is targeting August for his return, which would be just about one year out from his surgery last summer. That would be an ambitious timeframe, but if he is able to get back on the mound around then it’s possible the Red Sox could deal Jansen and transition right to Hendriks with minimal interruption.

Of course, if there ends up being a gap the Red Sox could opt for a closer by committee in the interim, and in that case Justin Slaten could factor into the equation occasionally. But big picture I don’t expect the club will want to throw Slaten in that spot, not this early in his career.

Long-term? Maybe, but that’s not something we need to worry about this year.

Contenders always need lefty arms out of the pen. Would Breslow entertain trading Bernardino at the deadline if the price was right? — Jason C.

If the price was right? Sure, but I don’t think Breslow is necessarily going to be looking to move Bernardino.

What would be the pros and cons of a Bernardino deal? The argument in favor might be that Bernardino is 32 years old, didn’t debut until he was already 30 and right now he might be as good as he’s ever going to be. So there’s some merit in potentially trading him now, maximizing his value and trying to find another left-hander to replace him.

On the other hand, Breslow’s stated goal is to improve the organization’s pitching depth from top to bottom, and Bernardino is one of the best relief pitchers on the staff, boasting a 0.78 ERA through his first 23 innings. More importantly, Bernardino will remain under team control through the 2029 season at a relatively affordable price, so from a team-building perspective Bernardino is arguably more valuable to the Red Sox than whatever prospect they could get for him in return.

If Bernardino were somehow able to command a Top 100 prospect then that might change things, but I have a hard time imagining any club would part ways with that kind of talent for someone with Bernardino’s profile.

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