Why free agents Dallas Keuchel and Craig Kimbrel could wait until after June 5 to sign

There is one big reason and one smaller reason why waiting could be advantageous

4/30/2019, 3:00 PM
Oct 16, 2018; Houston, TX, USA; Houston Astros starting pitcher Dallas Keuchel (60) walks off the mound after the third out in the first inning of game three of the 2018 ALCS playoff baseball series against the Boston Red Sox at Minute Maid Park. Mandatory Credit: Troy Taormina-USA TODAY Sports / Troy Taormina
Oct 16, 2018; Houston, TX, USA; Houston Astros starting pitcher Dallas Keuchel (60) walks off the mound after the third out in the first inning of game three of the 2018 ALCS playoff baseball series against the Boston Red Sox at Minute Maid Park. Mandatory Credit: Troy Taormina-USA TODAY Sports / Troy Taormina

A month of the 2019 season has passed and free agents Dallas Keuchel and Craig Kimbrel are still on the market. And the longer this plays out, the more it could make sense for one or both of them to wait until after June 5 to sign.

Here's why...

As free agents who rejected the $17.9 million qualifying offer from their respective teams, Keuchel (Red Sox) and Kimbrel (Astros) are both tied to draft pick compensation (a team's highest first-round pick is exempt) in this year's MLB Draft, which runs from June 3 to June 5.

If any team but their most recent former team signs Keuchel or Kimbrel before the draft, they will be forced to surrender a draft pick in the process. The exact pick that would have to be surrendered by each team is determined by a number of factors, including if the team received revenue sharing and the amount the player ultimately signs for. 

Along with the draft pick compensation tied to Keuchel and Kimbrel before the draft is over is the fact that most teams would also lose $500,000 from its international bonus pool for the upcoming signing period. 

However, if Keuchel and/or Kimbrel sign after the draft is over, the signing team(s) will not have to forfeit a draft pick or lose any international bonus pool money.

For teams that are trying to rebuild farm systems due to trades (Mets) or penalties (Braves), it could be much more advantageous to try to wait Keuchel or Kimbrel out.

And for teams who are targeting specific international free agents during the upcoming signing period, waiting this out makes tons of sense.

Translation: Waiting until after the draft could be smart for the interested teams and for Keuchel and Kimbrel -- whose markets could get more competitive with the draft pick compensation and bonus pool money aspect removed from the equation.

As far as how long it would take the pitchers to get ready, Keuchel has reportedly been throwing 95-pitch simulated games every five days to prepare. It's unclear what Kimbrel has been doing to prepare.

But as the calendar is about to flip from April to May, the idea that this could take another month and change to resolve itself doesn't seem so crazy.

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