What Red Sox would do if MLB Trade Deadline was today

By WEEI 93.7

It would have been 4 p.m. Friday.

That's when the annual anxiousness of a Major League Baseball season would have kicked in thanks to the annual trade deadline. But, alas, we will have to wait another month.

While the Red Sox still have until Aug. 31 to figure out their strategy, having played just seven games this season, it is eerie how similar their situation to one year ago is. Much like their current state, the 2019 Red Sox found themselves still in the thick of the postseason hunt teetering on trying to figure out what path should be taken at the deadline. As we remember, other than the early-July acquisition of Andrew Cashner they did nothing, leading Dave Dombrowski to offer this, "I think if we were closer to first place I would have been more open-minded to some of the other things."

Keep in mind, the Red Sox were just two games out of a Wild Card spot at the time.

And just like last year the Red Sox also now stare at a possible make-or-break stretch with the Yankees. In 2019, it was the four-game sweep from Aug. 2-4 that absolutely buried Alex Cora's team. That, of course, punctuated what would be an eight-game losing streak that also included three defeats to Tampa Bay at the end of July and Aug. 1.

Now you have three games in New York with another series against the Rays right after. And while the completion of this weekend will still leave the Red Sox with two more months in an eight-team playoff field, just about 1/6 of the entire season will have been played. In other words, these games mean something.

And while there aren't going to be any trades coming Friday afternoon, the Red Sox' approach to the deadline will also take a step toward being defined over the course of this road trip.

If the Red Sox go on a great run in the next week, like it or not, pennant fever will grip New England baseball fans (at least for a bit). If it ends up like a year ago -- like a year ago -- there won't be much debate regarding the approach. The benefit this team has this time around is that it won't be looking at the deadline in the rearview mirror if the wheels fall off.

So, where do things stand now?

One factor that can't be discounted is the difference in approach from Dombrowski to Chaim Bloom. The guess is that the current chief decision-maker will always be prioritizing the future, even if in the hunt, whereas the previous regime wanted to go for the here and the now.

The potential free-agent-to-be pieces to keep an eye on:

Jackie Bradley Jr.: He got off to a great start, but Ron Roenicke's willingness to pinch-hit for the outfielder and then sit him against a lefty starter might not allow for the value-build it seemed like he was trending toward during that first series of the season.

Brandon Workman: If the Red Sox find themselves in the mix, it would be difficult to deal away what appears to be their only real closing option right now. But we can't forget -- even though it was different times -- what trading late-inning reliever Andrew Miller in 2014 did, getting Eduardo Rodriguez from the Orioles.

Kevin Pillar: It would be interesting to see what the Red Sox could get for the 31-year-old if he remains hot. If that is the case, Pillar would seem like a perfect chip to send to a team potentially desperate to make a run at things.

Martin Perez: Normally, the starter would be a gift, representing a valuable trade chip if he pitched like he did Thursday night. But if the Red Sox are in it all, and the rotation remains looking like it is currently constructed, going into the month without Perez might be the ultimate waving of the white flag.

Jose Peraza: Peraza is on his way to making some money for himself, looking like the valuable all-around player many projected he would be in his younger days. Still, it is probably easier to sell the transition to someone like Tzu-Wei Lin or Michael Chavis if the Sox can get decent value back for him.

J.D. Martinez: Here's an idea, sweeten his money for the final two years and take those opt-outs off the table. Unless you are going to get a no-holds-barred, lock-down young starting pitcher for the designated hitter, the Red Sox have to prioritize keeping the slugger. Why? Because replacing him is just too hard.


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