Scott Boras' history lesson illustrates why Cubs are unlikely to trade Kris Bryant

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SCOTTSDALE, Ariz. — As the Cubs move into a new era, the Kris Bryant Decision looms large over the entire organization.

Should they trade him now, two years out from free agency (or one year away if he actually wins his service time grievance)? Or is now the time for the Cubs to deliver a huge offer and lock him up long term?

Bryant's agent, Scott Boras, has been one of the most powerful men in baseball over the last couple decades and he's seen many teams go through the same dilemma the Cubs are currently weighing.

In encountering similar situations with players of Bryant's caliber (a former MVP and Rookie of the Year), Boras shed some light on how unlikely it is that the Cubs would actually wind up dealing him.

"Certainly every player I have that is at that level, they're always asking the question about, 'will they? Won't they? Will they trade him? Will they do it?'" Boras said. "And the answer to that is always: I can give you a percentage over a decade of how many of those players get traded and the answer is very low. If you think that much of him and to get something back for him with a limited period of time is always very hard."

He's got a strong point there. Bryant has a career .901 OPS and averages 32 homers, 92 RBI and 112 runs scored per 162 games over his five years in the big leagues. He proved that the lack of power and production in 2018 was injury related with a strong bounceback season this past year, finishing 14th in WAR in the National League while battling through a lingering knee issue. 

Bryant provides a ton of value to the Cubs and his presence on the roster increases the likelihood of winning another World Series over the next two seasons. In order to trade him, they would need a huge haul in return — a package of players that sets the franchise up for success the future without completely sacrificing the short-term and current window of contention. Will some team actually meet the Cubs' asking price?

The service time grievance is a major issue here, as the difference between one and two years of Bryant would be vast. Red Sox star Mookie Betts is a free agent a year from now and Boston is in a similar situation in that they're weighing a potential trade now rather than risk losing Betts to the open market and getting only draft pick compensation in return.

Boras pointed to how the Red Sox and Cubs both won World Series with Betts and Bryant earlier in their careers, leveraging the star players on cheaper deals to allow more resources to augment the roster around them. But now both guys are due a hefty sum of money in 2020 (MLB Trade Rumors estimates the arbitration figure to be $18.5 million for Bryant and $27.7 million for Betts) and it's time for each team to decide which path to go down.

The prevailing thought around the game is that Bryant won't win his grievance, which puts the Cubs in a different spot than the Red Sox in that they have two years of control left. That's key to either dangle in a trade or to allow more time for the two sides to reach an agreement on an extension.

"I've seen clubs take this decision on and it's often been a decision that they regret — whether they've kept him or whether they've traded him," Boras said. "Again, because they're great players, they're really key decisions."

If no team is able to — or decides to — meet the Cubs' price for Bryant in any trade talks, how likely is it the two sides would work out an extension that keeps him in Chicago beyond 2021?

Both sides waved off any notion that the service time grievance has done anything to damage the relationship between Bryant and the club, with Boras emphasizing that this was a "union matter" and was more about being an "advocate for the rights of players." Even if the arbiter rules against Bryant's grievance, it could still be a major step forward in changing the structure of free agency and service time for the next Collective Bargaining Agreement.

In the matter of extension talks, Bryant and Boras are all ears.

"Look, we're open to talking with them and we've always said that to them," Boras said. "It's always been Kris' philosophy with the team. 

"I would certainly keep the terms and conditions of the contract negotiations private with the Cubs, but obviously it's always a fairness standard. You want what's fair for him and where he stands in the industry and that's true of any player." 

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