How an extra draft pick could alter Red Sox free agency plans

BOSTON, MA - OCTOBER 28: Chaim Bloom speaks as he is introduced as Boston Red Sox Chief Baseball Officer during a press conference on October 28, 2019 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - OCTOBER 28: Chaim Bloom speaks as he is introduced as Boston Red Sox Chief Baseball Officer during a press conference on October 28, 2019 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images) /

The Boston Red Sox could change their approach to free agency

Having an extra draft pick in his pocket could factor into how Boston Red Sox chief baseball officer Chaim Bloom approaches free agency.

Many of the top free agents are tied to a qualifying offer that will almost certainly be declined. That means it would cost another team their second-highest draft pick in order to sign them, with the former team receiving a compensation pick.

While signing a free agent who declined a qualifying offer was never completely off the table for Bloom, the long-term goal of rebuilding the farm system outweighed the immediate gain of signing one of the top targets on the market. Bloom has hinted that the Red Sox are better positioned to strike at that top-tier of free agency than they are a year ago, making it more likely that he would consider making a splash.

The tremendous job that Bloom has done turning one of the worst farm systems in baseball into one of the ten best along with a surprising postseason run that proved his rebuilding plan is ahead of schedule are primary factors that would lead Bloom to sacrifice a draft pick for that difference-maker who can put Boston over the top. There’s another reason why Bloom might be more comfortable paying a penalty for signing one of the top free agents though.

The Red Sox have the benefit of owning two second-round picks in the 2022 draft. Boston selected Jud Fabian with the No. 40 overall pick this year but failed to sign him when he decided to return to the University of Florida. The Red Sox will receive the No. 41 pick in next year’s draft as compensation for not signing Fabian.

According to MassLive’s Christopher Smith, that No. 41 overall pick is protected in the event that the Red Sox sign a free agent who declined a qualifying offer. It’s their other second-round pick that would be forfeit in that scenario. We don’t know the exact draft order since the compensation picks haven’t been established yet but the Red Sox will be picking in the bottom-10 of the round by virtue of their spot in the standings this year. The pick near the beginning of Round 2 is clearly more valuable than one at the end of the round and knowing that 41st pick is locked in makes their next pick somewhat more expendable.

Granted, the Red Sox might decide to keep both picks, not to mention the $500,000 in international bonus pool money that they would also be penalized for signing a free agent attached to a qualifying offer.

"“I think any transaction we make we have to factor in all the cost and benefits of that transaction. So we would do the same in this case,” Red Sox GM Brian O’Halloran said here at the GM Meetings on Wednesday."

There’s still a penalty to pay for signing one of these free agents but it doesn’t feel quite as steep with an extra draft pick to work with. The price might be worth paying when you consider the talent potentially available in this market. Freddie Freeman, Carlos Correa, Corey Seager, Marcus Semien, Robby Ray, Justin Verlander and Raisel Iglesias are just a sample of the star players attached to qualifying offers who might interest the Red Sox.

We should also note that the Red Sox extended a qualifying offer to Eduardo Rodriguez. Reports that they also have a multi-year offer on the table for the lefty along with growing interest from other suitors suggests Rodriguez is expected to decline the offer. Boston appears intent on re-signing him but they will receive a draft pick if he’s lured away by another team.

That compensation pick would further reduce the sting of being penalized for signing a top free agent. Let’s say the Red Sox were willing to let E-Rod walk in order to sign Ray. Boston would lose their draft pick near the end of the second round plus the international bonus pool money but they would still have the No. 41 pick plus a comp pick for losing Rodriguez. That seems like a fair trade off to upgrade their rotation with a pitcher who was arguably the front-runner for the AL Cy Young award this season.

Even if Bloom is more willing to pay this draft pick penalty, it doesn’t necessarily mean the Red Sox will be getting a top-tier free agent. Bloom has the restraint to avoid overpaying with a risky long-term deal so he could be outbid by more overzealous teams. At least he appears willing to try.

We’ve never seen Bloom reel in an elite talent in free agency but with the position the Red Sox are currently in, this might be the year.

Next. 3 free agent bullpen options. dark