Chicago Cubs: Roadblocks in a potential Jason Heyward trade

With under a week to go until pitchers and catchers report for Spring Training and both Bryce Harper and Manny Machado still unsigned, the Chicago Cubs might still be exploring options to move money around.

With the San Francisco Giants looking for outfield help, Buster Olney of ESPN reported that new GM Farhan Zaidi and crew are monitoring the market for veterans:

Although Olney has recently reported that the Giants may be interested in Jacoby Ellsbury, it would not be surprising if the Cubs engaged them in talks for a deal centered around Jason Heyward.

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The Giants have shown interest in Heyward before, reportedly exploring a deal prior to the 2018 season that would have sent Mark Melancon and former Cub Jeff Samardzija back to Chicago.

`And, in theory, the Giants are in desperate need of a veteran leader in the outfield. As of now, their outfield consists of Chris Shaw, Steven Duggar and Austin Slater, three young players with pretty minimal big-league experience.

But with Zaidi committed to a rebuild, how likely is it that the Cubs could swing a deal to clear up payroll?

Giants learning from past mistakes?

Last offseason, San Francisco made plenty of headlines when they traded for Evan Longoria and Andrew McCutchen in a span of three weeks.

Former general manager Bobby Evans and executive vice president of baseball operations Brian Sabean were hoping that the veterans would add run production and leadership at positions of need for a club looking to get back to the postseason.

Instead, both players struggled, and an early injury to ace Madison Bumgarner all but crushed San Francisco’s playoff hopes. The Giants promptly flipped McCutchen to the New York Yankees before the end of August.

It is worth noting that the Giants sacrificed a number of prospects and the likes of Kyle Crick–now one of the brightest bullpen arms in the game–to acquire both players.

The Cubs would likely be looking to add young arms in a deal for Heyward, and given Zaidi’s commitment to a rebuild and accumulating young talent, it seems unlikely that Theo Epstein and Jed Hoyer could get a suitable return.

Zaidi is turning over a new leaf in San Francisco. He has engaged numerous clubs in talks for players on expiring deals–including Bumgarner–while letting veterans like Hunter Strickland walk in free agency. He has similarly shown savvy in offering one-year deals to pitchers with a lot to prove, notably Derek Holland and Drew Pomeranz.

Even if the Giants have glaring outfield needs, it is unlikely that Zaidi would take on the rest of Heyward’s salary when he could gamble on the likes of Ellsbury at a cheaper rate, both in terms of money and return on investment.

The Cubs would need a guarantee

Sure, Heyward has hardly lived up to his contract in Chicago. But if the Cubs were to move the 29-year-old, they would be dealt a crushing blow to their outfield depth without assurances from one Bryce Harper.

It seems unlikely that Joe Maddon would be comfortable with a hypothetical starting outfield of Kyle Schwarber, Albert Almora and Ian Happ, especially given his affinity for platooning Happ and Almora against righties and lefties, respectively. And yet, that is exactly what his lineup card would look like with Heyward on the move and a failure to sign Harper.

And after all, what would be the point of moving money around and sacrificing Gold-Glove caliber defense and depth in the outfield only to miss out on the biggest marquee name in the game?