Chicago Cubs: Top salary dump moves the team could make

Anything goes – at least that’s what it seems like for the Chicago Cubs. Will the front office start dumping salary at this week’s Winter Meetings?

Major League Baseball’s annual Winter Meetings are underway in San Diego and it seems like we’ll be seeing more action than in recent years. Rumors and speculation are already swirling – and for the Cubs, that’s not necessarily a good thing – at least not if you want Chicago to contend in 2020.

The Cubs are faced with a lot of tough questions and decisions heading into 2020, but if they do the hard work now, the picture for this upcoming season (and beyond) will be much clearer. With a lot of money tied up in the current roster, we take a look at a few moves that could help dump some big salaries.

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1)    Trading Heyward to the Giants

Anytime salary is brought up, Jason Heyward is an obvious talking point. He is owed $23.5 million this season, taking up almost 13 percent of the team’s current payroll. Coming off a season where Heyward had a 2.0 WAR, a batting average of .251 with an OPS of .772, Cubs fans have always expected a little more from their right fielder.

He is outstanding in the field, a true leader and one heck of a teammate and the Cubs are lucky to have him. However, with what Chicago is trying to accomplish this offseason, looking at moving Heyward and his contract makes sense. Getting even some of that money off the books would give Theo Epstein much-needed flexibility in the coming months.

The San Francisco Giants would be the ideal partner for a Heyward deal. They are in need of a veteran outfielder. Not only that, but they have also expressed serious interest in Nicholas Castellanos. The Cubs are notably very interested in bringing Castellanos back, but are unsure if they can afford it. Sending their other right fielder, along with that massive contract, to another top contestant in the sweepstakes, would open the door for the Cubs to re-sign the fan favorite from 2019.

2)    Trading Lester to the Angels

This one is going to seem very controversial. One of (if not the) the best free agent signings in Cubs history without a doubt, Jon Lester is entering the sixth year of a $155 million deal, and is owed $20 million this season, almost 11 percent of the team’s payroll. Lester is coming off a season in which he had an ERA of 4.46, along with a league-leading 205 hits allowed. The big left-hander showed some serious fatigue as the 2019 season progressed.

He is a grinder and will give the Cubs every ounce he has, making him a great leader and competitor. But focusing on the financial aspect, seeing what is out there for Lester, would not be a bad idea. At 35, the southpaw may show some more regression, so seeing about dumping $20 million in salary, while pairing him with a younger pitching staff to lead and mentor, could be important for the Cubs financial situation.

The Angels are an interesting fit, as they are desperately looking to add pitching and have money to spend. Giving Lester the opportunity to reunite with Joe Maddon and help get Mike Trout to the postseason would be an entertaining story.

The Cubs would no doubt have a tough time making a deal for one of these two veteran leaders, but shopping around would not be a bad idea, by any means. Epstein is big on the ‘no untouchables’ mantra and here should be no exception.

I love Lester and Heyward more than the next fan, but the Cubs need to add an impact starter and bat and the financial flexibility would be there by dumping even some of these unsightly salaries.