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Let’s Get Ready To Rumble

What do the following players all have in common: Gerrit Cole, Stephen Strasburg, Anthony Rendon, Nicholas Castellanos, Hyun-Jin Ryu, “Diamond” Dallas Keuchel?  They’re all free agents currently.  Oh wait, and they’re all represented by super agent, Scott Boras.  All of these names, aside from the first three mentioned, have been linked in some way to the White Sox this winter.  To an extent, one can argue that the fate of the White Sox 2020 season will come down the battle that has waged on for close to two decades between the Sox 83-year-old owner, Jerry Reinsdorf, and Boras.

The Sox problems with Boras in recent years have been very well documented.  Boras has recently come out with positive words about the organization, stating that players are viewing them differently than even a year ago, due to their improving core of talent at the Major League level, with a few reinforcements still to come from the minors.  But what were the origins of this feud between our boys and the most powerful agent in the sport? 

Things began to take a turn for the worse in June of 1997 when the Sox selected Boras client, Jeff Weaver, in the 2nd round of the amateur draft.  After a contentious negotiation, discussions broke down between the two sides.  This came on the heels of the Sox failing to sign their top draft pick and Boras client, Bobby Seay, the prior year.  These draft failures caused the Sox to shy away from selecting Boras clients in subsequent drafts.

Waters were muddied even further in the winter of 2000.  Fresh off a surprising division championship, the Sox were linked to the top free agent prize that winter, 25-year-old shortstop, Alex Rodriguez.  Urban legends have told tales that the Sox made an offer for the superstar Rodriguez in the, try not to laugh, $200M range over the course of 10 years.  As the story goes, Boras gave Reinsdorf a verbal assurance that he would “circle back” to him before finalizing an agreement with A-Rod.  Low and behold, A-Rod signed his then record 10 year, $250M deal with the Texas Rangers.  Incensed by Boras, seemingly, breaking his word to come back to the Sox, the organization vowed to stop doing business with the agent.

In the years that have followed, the Sox have really done very little business with Boras and his clients.  There was the Andruw Jones pillow contract in 2010 following his three disastrous seasons with the Dodgers and Rangers.  The Sox then selected Carlos Rodon with the 3rd pick in the 2014 draft.  It should be noted that his selection was heavily aided by hard slots on amateur signing bonuses, which I’m sure made things very palatable to a certain 83-year-old.  There was a brief flirtation with Bryce Harper last winter, which went nowhere much to the shock of many.  Boy, wouldn’t that left-handed bat in right field look nice right now? However, that’s a discussion for another day.

So where does that leave the Sox now?  If the Sox are truly going to make strides towards ending their post-season drought, they must start working with Boras.  This man represents the top talent in the game on an annual basis and if this team truly means they want to build sustained success, procuring his clients, when possible, is a must.  Given the recent failure to secure Zack Wheeler, I would look to bring in Ryu on a three to four year deal, personally.  Keuchel, although a prior Cy Young Award winner, just doesn’t excite me and doesn’t bring the upside that fans have seen from Ryu the last two seasons.  That isn’t to say that Ryu is without his warts, given his spotty injury history.  In any event, I would think that the Sox have a desire to ensure stability in their rotation, which can be accomplished with either one of these southpaws.

It’s time for this two decade long feud between the Sox and Scott Boras to end.  The man isn’t going away any time soon, and he will continue to represent the top talent in the sport.  If Boras is operating at a 10% commission rate, for simplicity sake, he is looking to pocket somewhere around $80M himself in the coming months with all his high profile clients this winter.  The man is the leader in his profession for a reason, and the Sox need to stop running from him.  If they put their head down and bare the financial repercussions of negotiating with Boras and secure some of his clients this winter, this team will be far better situated to give fans a fun summer at 35th/Shields.


Featured Photo: Getty, AP

Former scrub JUCO pitcher

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