Red Sox’s Most Interesting Trade Deadline Wild Cards

As the Boston Red Sox fight to save their season from early extinction, they’ve got no shortage of players who could be headed for new cities come the first week of August.

Boston’s first two months and change have been incredibly disappointing, there’s no doubt about it. Had things played out differently across the league, they might already be making their plans to sell at the deadline. But because they’re still mathematically in the playoff race due to a weak American League, we can’t yet say with certainty that selling is the plan.

So as we prepare for what seems like a longer sprint to the trade deadline year after year, this year’s Red Sox deadline, let’s discuss some of the players who represent unexpectedly intriguing dilemmas for Boston this year. For lack of a better term, we’ll call them Boston’s X-factors.

Does Isiah Kiner-Falefa become a real trade chip?

Based on how poorly he’s hit for most of his career, Kiner-Falefa wasn’t a guy many Red Sox fans had high hopes for coming into the year. He’s been one of the most consistent hitters on the club since the middle of May, however, and is one of the main reasons the offense has been better since Trevor Story got injured.

Because he’s a rental, the Red Sox will have incentive to offload Kiner-Falefa no matter what if they become sellers. But it would be a serious boost to the team’s future outlook if he keeps hitting this well and prompts some team to give up a legitimate prospect to bring him in for the stretch run.

What happens with Masataka Yoshida?

If the Red Sox could have gotten a team to eat a significant portion of Yoshida’s contract without giving up any prospect capital by now, it’s likely that would have happened already. Though the deal will be up after next year, it’s universally considered one of the worst contracts in the game these days.

So will the Red Sox finally capitulate and do something like their Jordan Hicks trade with the Chicago White Sox? With a ton of middle infielders in the low levels of the minor leagues, maybe it makes sense to part ways with someone while their value is high and get as much of Yoshida’s money out of the picture as possible to improve next year’s financial outlook.

Is it the right time to cash in on Garrett Whitlock?

Assuming Whitlock is healthy again and pitching close to his usual standard by the time trade talks really heat up a couple of weeks before the deadline, he’s bound to be one of the most coveted relievers who could conceivably be available. He’s under team control through 2028 at a very reasonable cost, and he’s one of the few bullpen guys in the league who has virtually no platoon splits, which is a huge plus in high-leverage situations.

But even if the Red Sox are in the tank by late July and selling off guys like Aroldis Chapman and Sonny Gray, Whitlock could still be seen as an important piece of next year’s roster, for a team that would still have every intention of contending. So will somebody blow the Red Sox away with an offer they can’t turn down?

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