Chicago Cubs: Who will be making the most money in 2020?

Chicago Cubs: While the team will be shedding a solid amount of payroll this offseason, there are still big contracts still set in place for 2020.

One of the biggest questions being asked by Chicago Cubs fans right now heading into an offseason with a lot of uncertainty is how much money will be spent to fix some holes. Will changes even come via spending a lot of money? I mean, we are seeing the Oakland A’s and Tampa Bay Rays play October baseball with much smaller payrolls.

The Cubs will still have one of the biggest payrolls in baseball regardless of how much they spend this offseason. While guys like Cole Hamels, Ben Zobrist, Pedro Strop and (likely) Addison Russell are coming off the books, there are still a lot of players under big contracts for 2020 and beyond. All of this obviously plays a role in the what the future holds for the likes of Kris Bryant, Javier Baez and Willson Contreras.

2020 is going to have a number of arbitration years on top of contracts already put in place, and who knows for sure who the Cubs sign, but here is a sum up of the guys who are already set to make the most money in 2020.

Chicago Cubs: Hard to believe this is year five of Heyward

Jason Heyward signed the eight-year, $184 million deal in December of 2015. The finale of the 2019 season will officially mark the halfway point of the contract. Money is guaranteed and currently has a modified no-trade clause through 2020 until it becomes a full no-trade clause the year after.

Have the overall numbers justified roughly $23 million a year? No. That is however not to say he has not made positive impacts for the team. He will finish the season with 20+ homers, a .340+ OBP and roughly .770 OPS. His multiple Gold Gloves in Chicago certainly don’t go unnoticed, either. Let’s face it though he is making A LOT of money.

Next season he will earn $23.5 million, which right now is set to be the most on the team. His base salary will be $21 million with the $2.5 million signing bonus on top of that. If he somehow were to get traded this offseason, no doubt the Cubs would have to eat a chunk of the cash but for right now count on Heyward suiting up in blue next year.

Chicago Cubs: Time goes by fast, especially when you have fun.

Very late at night on December 10, 2014, the Chicago Cubs won the Jon Lester sweepstakes. A six-year, $155 million deal was agreed upon between the Cubs and Lester, which would begin what has become one of the team’s greatest free agent signings ever.

After two All Star appearances, NLCS MVP honors and of course a World Series championship, the clock is winding down on old Jon. He has one more guaranteed year left on his deal for 2020, in which he will make $20 million. That is $15 million in base salary and $5 million in signing bonus money. It will be the smallest annual salary for him since his first year in 2015.

Note that 2021 has a $25 million vested option with a $10 million buyout. Lester would have to accumulate 400 innings between 2019 and 2020 or pitch 200 innings in 2020. With the way things are trending both with age and declining performance, Lester’s last year as a Cubs is going to be 2020.

Worth every penny.

Chicago Cubs: Lets see how this man responds to a normal offseason.

The numbers for Craig Kimbrel in 2019 are pretty ugly…and his season ended in gut-wrenching fashion against the Cardinals a week back. However we can give a guy who signed mid-season and dealt with injuries throughout his first tenure in Chicago the benefit of the doubt, for now.

Kimbrel will make $16 million in 2020 to be the Cubs closer. There is going to be some big changes in that pen and hopefully starting off the season with a fully armed and operational Kimbrel will avoid some of the early troubles they saw in 2019. He is simply going to need to be the guy who entered 2019 with a career 1.91 ERA, 1.96 FIP and 14.7 K/9.

So lets add those four guys up. In total that is $81.5 million worth in payroll next season. To put that in perspective, the 2019 Oakland Athletics total payroll is roughly $110.5 million. Four guys on one team are making up roughly 74% of what Oakland’s payroll is. Pretty insane.