Look, there is no way to sugar coat it, the Jason Heyward contract is about the biggest dumpster fire of a contract there may ever be.  Having said that, everyone receives one mulligan. 

Even 3 time World Series winning GM Brian Sabean has had a horrible Matt Cain contract to contend with the last half decade.

Theo Epstein hasn’t made too many blunders – and winning a World Series with both the Red Sox and now the Cubs has solidified a position for him in Cooperstown.

Also lucky is the brilliant signing of Anthony Rizzo of a 7 YR deal prior to 2013, and when he asserted himself as a perennial MVP contender.

Despite carrying a projected payroll in 2017 of around $171 MIL – the team has plenty of expiring contracts in the name of Jake Arrieta, Wade Davis, Jon Lackey, Jon Jay, Pedro Strop, Miguel Montero and Koji Uehara. to replenisg te talent again in 2018 – and going forward

There are only 4 players signed for $79.2 MIL so far.

The Rizzo longterm deal a perfect contrast to the Heyward pact. Should Rizzo’s Team Options be picked up for 2020 and 2021 (for $16.5 MIL each year), then the club will still only have paid him $74 MIL from 2013 – 2021, spanning 9 years at an Annual Value of $8.2 MIL. That is completely lights out for the organization going forward.

The one factor of brilliantly drafting and then rostering a club full of guys the same age is that they are all on entry level contracts for a few years before the squad becomes increasingly expensive before Arbitration rights kick in.

2018 will see Kris Bryant, Kyle Hendricks and Addison Russell all hit 1st year Eligible on Arbitration, and then 2019 has Javier Baez, Kyle Schwarber, Willson Contreras and Carl Edwards JR. hit the 1st year. 

it will be at this point the team shoots up the salary page.

Other than Jon Lester, Heyward and Ben Zobrist,  there are no real big salaries on the table for the team to digest.

The biggest dilemma will be the status of Jake Arrieta.  My guess is that he will want too much money and walk away from the Cubs.

More important than that even is simply signing Free Agents (not named Arrieta) by Epstein.

Epstein is creative.  It is okay to figure out a Starting Pitcher in Free Agency, and also add another Closer if need be.  Who knows, by 2018, Hector Rondon and Carl Edwards JR. may be able to lock down that role.

There is still money to spend in the 2017 and 2018 winter markets for sure.

Also playing in the NL Central provides them with security of being able to outspend all the other teams – with the Cardinals only being in the atmosphere.

It is not like they are fighting in the tough NL West with the Giants and high spending Dodgers.  It will still mean facing off against those clubs. and contending with the aging Nationals roster, and New York Mets young staff for a few seasons.

Wrigley Field will be sold out, the revenue streams will break out to record levels, all freely flowing cash into the Ricketts family pockets.

The good news is they are not in cap hell yet  The bad news is that it would only take one more bad deal/paired with Heyward, in order to prevent the club from signing all of their young superstars to extensions.

Epstein is too smart for that.  Look for high value Annual Average Value’s that have expiring contracts before the 2018 and 2019 seasons.  I wouldn’t be surprised if they trade for an existing ace pitcher.

Think Zack Greinke now, or a guy like Justin Verlander in 2018 or 2019, where the other club may eat some of the salary, ask for a high level prospect, and then have a legitimate Starter to lug some innings in the playoffs.

I also wouldn’t be surprised if the brass orchestrates a trade for a guy like Chris Archer – or Sonny Gray (midway through this year if he has healed himself).

Maybe it would cost you a Javier Baez, or a combinations of Carl Edwards JR./Albert Almora JR. to do it, however with Ben Zobrist still in town, defense alignment can be configured in a lot of different ways for at least the next 2 – 3 years.

Like I stated in the Giants Payroll article, the new CBA has also reeled in the Dodgers spending $300 MIL on team payroll.  The best thing that could happen for the Cubs is if Clayton Kershaw were to opt out of his deal beyond 2017.

That would either bring up the price for the Dodgers to sign him, or even give them the chance to sign the guy themselves.  Yes. the Cubs have more flexibility than the Dodgers for at least a couple of offseasons.

Guaranteed Contracts/POS/AGE:

Jason Heyward – OF (28):  With a grand sum of $184 MIL from 2016 – 2023 ( 8 years) this is a brutal deal – and the club is lucky to have already won a World Series in season 1 of this pact.

Heyward will make an astonishing $28.2 MIL for both the 2017 and 2018 seasons.  Epstein at least frontloaded the contract to erase some of the burden by the time the young talent comes up for raises.

This deal is the 13th richest in history for a guy who carried a .631 OPS. in 2016  I tend to think that Heyward will be closer to his Career OPS of .761 the next few years with the pressure somewhat off him now. 

Hit him 7th or 8th and let him work out his kinks. Defense is at least not a problem here with him winning a 4th Gold Glove.

This could end bad in 2017 – with Heyward riding pine for some of the year – if the club opts to use Zobrist, Schwarber and the tandem of Jon Jay and Almora JR. as the OF.

You also have to think that Joe Maddon won’t hesitate to find Willson Contreras reps as well.

Jon Lester – SP (33):  Lester is in the 3rd year of a 7 YR/$165 MIL deal, and is set to reel in $25 MIL in 2017. The deal calls for $27.5 MIL in both 2018 and 2019, before scaling back to $20 MIL in 2020. 

There is a 2021 Club Option as well. Details on that: $25M Team Option, $10M Buyout option guaranteed with 200 innings in 2020 or 400 IP in 2019-20. 

With the Buyout that large, the man would have to fall from grace hard, to not get the Option.  Although he would be nearly 40, $15 MIL extra will probably not be that bad.

Lester is worth every dollar the club has spent so far.  It is hard to find playoff proven commodities on the open market.

Ben Zobrist – UT (36):  Zobrist is the only player in the MLB who was won 2 straight World Series, as also being a member of the 2015 WS Champ KC Royals.

With the availability to play 5 defensive positions, Zobrist was the perfect compliment to the Cubs defensive roster in 2016 – although he played predominantly at 2B. 

With the emergence of Baez in the playoffs, he will likely rove more around in 2017.

Zobrist earns $16.5 MIL in both 2017 and 2018 – before retreating back to $12.5 MIL in 2019.  He will be in his Age 39 season at that point, and it may not look so hot at that point, but one can’t argue at his flexibility on the Roster providing so many options in the title run.

You can even say that his positional switching gives the club a better chance to hold onto Kyle Schwarber (instead of trading him in the American League).

John Lackey – SP (38):  Lackey joined Lester, David Ross. and Epstein as guys who have won World Series in 2013 with Boston and the Cubs in 2016.  He will make $16 MIL in 2017 before hitting Free Agency in 2018.

Lackey lugged 188.1 IP and gave the Cubs a 3.35 ERA in the process.  It doesn’t even matter that he was being pulled in the early innings of the postseason.

Jake Arrieta – SP (31):  Arrieta earns a tidy $15.6 MIL this year and will likely head out into Free Agency as a Scott Boras client.  Unfortunately the man is going to be 32 heading into 2018.

I would not offer him higher than a 4 year deal at $20 – $21 MIL after, yet that will not get the job done when he hits the open market.  Someone will pony up 5 YRs/$125 MIL for him, you watch.

Miguel Montero – C (34);  Montero will make $14 MIL in 2017 – and I am not sure he will Catch more than about 60 games.  Contreras at last is on an entry level contract to offset this salary.  I am surprised the team has not ventured out to trade him.

Wade Davis – CL (32):  It cost the club Jorge Soler and 4 years of Team Control, yet this was the way to go.  $10 MIL for one year of Davis (who Closed for the 2015 wS Champion Royals) is smart business practice.

To acquire an elite Reliever such as this is a great move – when you consider the Yankees, Dodgers and Giants spent $86 MIL, $80 MIL and $62 MIL to sign Aroldis Chapman, Kenley Jansen and Mark Melancon respectively.

Soler was going to be their 7th option as an OF.  Davis, by the way, has a 0.83 ERA in 32.2 IP for his postseason career – and has carried a mid 1 ERA from 2014 – 2016 as a late inning Reliever – spanning 183 IP.

I would also think the club will extend the Qualifying Offer to him this winter ( $17.5 – $19 MIL range for one year), so they may even recover a 2nd or 3rd Draft Pick back all for just $10 MIL.

Jon Jay – OF (32): Has a 2017 contract or $8 MIL to play OF.  He has a career .352 OBP, so could hit 1st or 9th for Maddon, working as an on base guy for the big boppers.  Brilliant little move.

Anthony Rizzo – 1B (28):  Rizzo will take him $7 MIL for 2017, coming after the heels of an ALL-Star, Gold Glove, Silver Slugger and top 4 MVP season in which he clubbed 30+ HRs and added 100 RBI for a 2nd straight season.

Rizzo also makes $7 MIL in 2018, $12 MIL in 2019, and two Team Options in a row call for $16.5 MIL and $2 MIL Buyouts for both 2020 and 2021.

It is contracts like this that setup championship caliber clubs for the organization.

Other valued deals that compare to it last decade or so.  Paul Goldschmidt (5 YRs/$32.5 MIL), Madison Bumgarner (6 YRS/$35.6 MIL) and Andrew McCutchen ( 6 YRs/$51 MIL)  that coincided with 4 straight top 5 NL MVP finishes.

Rizzo should challenge for an MVP every year of that remains on this deal.

Koji Uehara – RP (42):  $6 MIL for one year seems like a lot or a guy of his age, but Uehara has plenty of playoff/Closer experience that is invaluable to a club like this.  I would take it easy on him in the regular season and save the bullets for playoffs.

Hector Rondon – RP (29):  $5.8 MIL for this former Closer is not a bad deal in 2017. Rondon has one more year left of Arbitration before hitting Free Agency in 2019.  He has 77 Saves and a career ERA of 2.97.

Brian Duensing – SP/RP (33):  Makes $2 MIL in 2017 and a Free Agent in 2018. A spot start here and extra Bullpen arm,

Justin Grimm – RP (29): Avoided Arbitration with a $1.8 MIL, has 2 more years left of Arbitration before he is a Free Agent.

Total Money for this Category for 2017: $157.5 MIL (13 Players)

Arbitration Eligible/POS/AGE

3rd  year

Pedro Strop – RP (33):  Is projected to to earn $5.5 MIL in Arbitration, and is a Free Agent in 2018.

Total Money for this Category for 2017: $5.5 MI:  Total money is now $163 MIL

Pre-Arbitration – Entry Level Contracts:

Tommy La Stella – INF (28):  Is Arbitration Eligible from 2018 – 2020 and a Free Agent in 2021.

Kyle Hendricks – SP (27): Is Arbitration Eligible from 2018 – 2020 and a Free Agent in 2021.

Kris Bryant – 3B Is Arbitration Eligible from 2018 – 2021 as a “Super 2” and a Free Agent in 2021.  Bryant is only 25 Years old, and will have 4 years of Arbitration kick in starting next season.

Since the club opted to start his 2015 after the 10 days of service time, they wll retian his rights until the end of 2021.  Bryant is on pace to end up recording Arbitration cash if he keeps his career trajectory.

The club should really look to extend him similar to the Mike Trout 6 YRs.$144 MIL deal he got.

Addison Russell – SS (23):  Is Arbitration Eligible from 2018 – 2021 as a “Super 2” and a Free Agent in 2022.

Comparisons to an extension similar to what he may get are:  Jason Kipnis and Matt Carpenter (6 YRs and $52 MIL)

Matt Szczur – UT (28): Is Arbitration Eligible from 2019 – 2021 and a Free Agent in 2022.

Javier Baez – 2B/3B (24):  Is Arbitration Eligible from 2019 – 2021 and a Free Agent in 2022.

Mike Montgomery – SP/RP (29): Is Arbitration Eligible from 2019 – 2021 and a Free Agent in 2022.

Kyle Schwarber – OF (24): Is Arbitration Eligible from 2019 – 2021 and a Free Agent in 2022.

Willson Contreras – C (25): Is Arbitration Eligible from 2022 – 2022 and a Free Agent in 2023.

Albert Almora JR – OF (23):   Is Arbitration Eligible from 2022 – 2022 and a Free Agent in 2023.

Rob Zastryzny – RP (25) Is Arbitration Eligible from 2022 – 2022 and a Free Agent in 2023.

Total Money for this Category for 2017: $6.0 MIL MIL Toral Money Oveall – $169.0 MIL

Buyouts/Dead Money

Jason Hammel – $2 Million Buyout for 2017 that was agreed to in a gentleman’s deal. There is no dead money on he books past 2017 thus far.

Conclusions:

Despite the Heyward mistake of a deal, Epstein has done everything right.  It will be a constant maneuvering of the incoming talent – to surround the plethora of young superstars the club has.

The Cubs have the availability to sign an elite pitcher in Free Agency in the year or 2, or trade for one.  Beyond that, the team can’t make another top 50 ALL – Time Salary roster mistake.

The brass should also investigate early extensions for Bryant, Ruseell and Contreras immediately while they may afford to wait for Hendricks and Schwarber yet. 

Some sort of guaranteed money to the budget would be wise

As for Arrieta, he is just too old – an unorthodox in order to grant him the cash he will seek.  Epstein has to find creative ways to bring in a #1 or $2 beyond this campaign. 

Chicago is fantastic shape financially to spend as much as it takes to ensure a dynasty in the next half-dozen years. 

If I were in charge I would try to limit any big historic contracts to their own young superstars from this point forwards. 

Also don’t be afraid to trade one of the premiere young offensive players for a quality Starter (#1 or #2 Starter)like Baez, Contreras or Almora.

Follow @chuckbooth3024 @mlbreports

*** The views and opinions expressed in this report are those of the author and do not necessarily reflect the views of mlbreports.com and their partners***

I am happy to be back at the helm of the MLB Reports, after completing my record 224 Games in the MLB Trip in 2015.  It was the 4th time I have seen all 30 MLB Parks since 2008. During that time away I was fortunate to do 100 Media Interviews

To Subscribe and listen daily to  ‘Our Lead Personality’  Sully’s 20 Minutes Daily (every day since Oct.24, 2012) Podcast click here.  Guaranteed listening to the Sully Baseball Daily Podcast will be the best time you invest in online!