Cubs Insider Predicts the Contracts and Landing Spots of MLB’s Top 10 Free Agents

You may recognize Michael Canter from his frequent contributions to the comments section, or maybe from another guest post from a while back. Well, after he drunk-uncled me the other day with encouragement to be better and have faith in myself, I decided to put the shoe on the other foot. Sort of. Mike dropped some knowledge about potential landing spots for several top free agents and I exhorted him to flesh it out a bit more.

What follows is his response to me:

1. David Price – Cubs [7/$220M]

This is a no-brainer. It is such a perfect fit I’d bet the Cubs had a prepared contract 30 seconds after the last out of the NLCS, with everything executed by ownership except the dollars and the years. Too many people with insider knowledge are saying Price to the Cubs, and I am not going to be one of the over-thinkers in the Cubs blogosphere that tries to reason against this signing. I will go one step further. I expect this to be the first of the SP dominos to fall and it will be before Christmas.

2. Jason Heyward – White Sox [10/$200M]

This will come with an out clause: a) Heyward is young; and b) that way I can say he really isn’t a $200M player because I don’t think he really is a $200M player. But the offseason buzzspeak will be defense and runs saved — ad nauseam, as framing was last winter — and Heyward is the king of OF defense. Look, the White Sox had arguably the best rotation in baseball last season despite a defense that did everything humanly possible to lose games. If I had to choose one free agent to go to a team where he would have the most profound impact, Heyward to the White Sox fits that description. Rick Hahn is smarter than I am and he knows Heyward could singlehandedly turn this team around. But this is the ceiling the White Sox will spend on one player. On the flip side, the $200M will be worth every single penny of wear and tear saved on Chris Sale’s arm.

3. Zack Greinke – Yankees [7/$189M]

I can see the NY Post headline: GREINKE A YANKEE. This deal sets the bar for the Jake Arrieta futures contract and moves Greinke from the current most-hated team in baseball to the former most-hated team in baseball. Even without Papa George, the Steinbrenner family dislikes being upstaged by the Mets. Greinke brings the buzz back to the Bronx and back to Yankees baseball. He is the most sure thing of any pitcher on the market and were he 2 years younger we might me talking about a 10/$300M deal here.

4. Justin Upton – Cardinals (ugh) [7/$160M]

This sickens me because Upton WILL realize his full potential in St. Louis. He is a Cubs killer and with Heyward leaving and Holliday coming off the books in 2017, this is something the Cardinals can easily afford. The Cardinals never have lean years. Their farm system is an All-Star pathway and they spend frugally and wisely when purchasing baseball players. When a player like Justin Upton becomes available, they pounce. Cubs fans, grab the TUMS and the whiskey.

5. Chris Davis – Astros [6/$130M]

He strikes out a lot. He hits a lot of home runs. He sounds like an Astro already. Eventually (like as soon as 2017) he will DH. And he will hit 60 HR playing 81 games in Houston, provided he stays healthy.

6. Yoenis Cespedes – No clue [6/$130M]

I drew a team out of a hat. It came up ‘New York Yankees,’ but with no QO he could go anywhere and I mean anywhere. On the surface he seems like a PERFECT fit for Seattle and I lean heavily toward the Emerald City as a destination for Cespedes except I don’t know if Cespedes thinks Seattle is a fit for his services, personally. I also don’t buy into the speculation that the last seven weeks of the season padded his potential contract numbers, but it certainly didn’t hurt him. He is a $100M player, but the obscene bidding for his services without the loss of a draft pick attached to his signing, not a few weeks of insane baseball, will inflate his value. He has been a hot streak/cold streak offensive player his entire career, so you know what you are getting with Cespedes. I know Theo Epstein loves him, but I don’t see the Cubs biting.

7. Jordan Zimmermann – Red Sox [6/$130M]

I like Zimmerman for the Cubs. I think he would be a beast in Wrigley Field by breaking a lot of opposing bats (I can almost see the Evan Altman-inspired ‘Breaking Bat’ t-shirt design in my head), by keeping the ground crew busy fixing infield divots, and by striking out Cardinals and Pirates by the dozens and just being a beacon of beastly nastiness in blue pinstripes. But I think the Red Sox will get him and he will instantly legitimize a staff that looks a lot better with Zimmerman as a 1, Buchholz as a 2, Porcello as a 3, Rodriguez as a 4 and Miley as a 5. With that OF defense for a full season (Betts, Bradley, Castillo), that looks to be an insane rotation in the AL East.

8. Johnny Cueto – Dodgers [6/$125M]

Well, they lost Greinke and with Mattingly gone I don’t think Greinke’s coming back. The Dodgers slide all the way down to SP 5A. This is a good fit for both player and team provided Cueto is healthy. The Dodgers have a lot of moves to make. They can easily acquire SP through trade as well but I can also see them saving the Cueto/Greinke money and signing Jeff Samardzija and Mike Leake and then trading for a guy like Danny Salazar. The Dodgers have as many open options as the Cubs do and I’d bet Andrew Friedman would rather hedge that money across numerous players than put all his eggs in one basket. Still, Cueto makes a lot of sense for this team, again, provided he is healthy.

9. Alex Gordon – Royals [5/$100M]

He is NEVER leaving Kansas City. Never. Cubs fans should just forget about this guy coming to Chicago. Gordon will be working in that FO with George Brett one day and he will be buried in Royal Blue when he dies.

10. John Lackey – Cubs [3/$45M]

You hate him on the Cardinals. You will love him on the Cubs. He is not a $15M per year pitcher at this stage of his career but he will get that from the Cubs in creative, vastly deferred fashion. This signing would probably mean the Cubs will jettison Jason Hammel. I think Lackey is nearly illiterate (how else do you explain taking a minimum-salaried year at the end of his deal in his age 34 season? He had to have misread that contract, right? Or maybe he just can’t read), but he would be a bulldog on a Cubs team full of bulldogs.

Other potential signings I like:

Ben Zobrist – Cubs
Jeff Samardzija – Dodgers, Tigers or Cardinals
Scott Kazmir – Tigers
Dexter Fowler – Mets
Ian Desmond – Mets
Howie Kendrick – White Sox
Austin Jackson – Cubs
Denard Span – Mariners
Brett Anderson – Pirates
JA Happ – Royals
Doug Fister – Red Sox
David Freese – White Sox
Tyler Clippard – Cubs

My only disclaimer here: trades will change the free agent landscape a great deal and I expect this winter to be just as active as last winter.

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