Chicago Cubs: Looking ahead: Who gets the first extension?

The Chicago Cubs possess an enviable crop of young players. For fun, let’s look at all the pros and cons of extending each one, and who will get the first one.

With all the young players the Chicago Cubs have, it’s an exciting time to be a fan of the World Series champions. Throw in the fact that all are under contract for the next few years and it appears the team will only get better.

However, one of the most important lessons one can instill in their head is that nothing lasts forever. With that being said, it’s best not to get too attached to the current club, as they will not be together forever.

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Nonetheless some of the current young players are certain to get extensions; they’re too good not to.

It’ll be interesting to see how Theo Epstein and co. approach the situation, as they don’t have to extend anyone now, though they may save some money down the line if they do.

It’s inevitable that extension[s] will be handed out. The question is, who will get the first one?

Below we’ll list some players we feel have the best shot at getting extended first, along with the pros and cons of doing so.

Addison Russell

Russell is a defensive stud and is a budding power bat. Drilling 21 homers and driving in 95 runs as a 22-year-old shortstop is impressive, and he’s definitely going to get better. An extension now would be very expensive, but could be worth it.

Pros: Russell is already extremely important to the Cubs. He’s only going to get better and, like Báez, locking him up now could save big money long-term. He’s proven himself as a threat at the plate and is one of the best defensive infielders in all of baseball.

Cons: Russell’s agent is Scott Boras, who’s notorious for getting his clients to free agency. Unless the extension is massive, it looks like the young shortstop will reach the open market.

Kyle Schwarber

Arguably a Cubs legend already, Schwarber is an exciting slugger who has 40-homer potential written all over him. Although he’s batting leadoff right now, he could end up being an impact middle-of-the-order hitter for someone.

Pros: Being that he’s got so little experience, an extension could come cheaper right now than down the road. If Schwarber does end up reaching huge home run totals, then he may get too expensive.

Cons: Defensively he still needs work, and while he did make an unbelievable catch earlier this week there’s no defintiive spot for him yet. He could also very well end up being traded if a need arises, so waiting may be best before extending him.

Kyle Hendricks

Last year’s breakout star, the soft-tossing Hendricks is coming into his own. Although he’s somewhat struggling so far this season, there’s no reason to think he won’t be at least an above-average starter for the foreseeable future.

Pros: The Cubs need pitching moving forward. Jake Arrieta and John Lackey both hit free agency at season’s end. Not to mention Brett Anderson continuing to battle health issues. Hendricks is young, appears to be getting better and would come at a reasonable price.

Cons: Perhaps waiting until how he performs after his career year to explore extension talks would be best. After all, he could fall back down to earth and perform as more of a middle-of-the-rotation arm instead of an ace.

Willson Contreras

Older than most of the young crop, Contreras has shown he’s one of the best defensive catchers in the game thanks to his absolute cannon of an arm. Offensively he’s coming along and could end up being one of the best all-around catchers in baseball.

Pros: Rumors surfaced that Contreras and the Cubs were already talking extensions in the offseason, though nothing came of it. He’s already a defensive stud and he’ll most likely be cheaper than the others.

Cons: Contreras’ inexperience is a bit of an issue. Waiting until he proves himself over time could be beneficial. This season, we’ve seen him display horrendous plate discipline at times and a lack of pop in the bat.

Kris Bryant

The best player on the team, a Bryant extension won’t come cheap. Tom Verducci of Sports Illustrated said extension talks this offseason “went nowhere” and Bryant himself said he’s focused on ‘playing it out’ rather than worrying about any deal.

Pros: Bryant is a monster, plain and simple. His first two big-league seasons rank among the best for any player ever. Without him, the Cubs don’t win a World Series. An extension will almost definitely be a record-setting one, but it’ll also definitely be worth it for the franchise.

Cons: Like Russell, Bryant’s agent is Boras, so the MVP will most likely hit free agency, unless the extension is one he can’t refuse. With Bryant it’s not why he shouldn’t get an extension, it’s more a matter of how.

Anthony Rizzo

The leader of the team, Rizzo is already serving an extension – a cheap one at that. One of the most reliable players in baseball, it’ll be hard to see the slugger go after all he’s done.

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Pros: As previously mentioned, Rizzo is the leader of the team. Making sure he’s locked up throughout the rest of his prime would be wise, and of course he’ll be worth it.

Cons: Perhaps the least likely to even get an extension, let alone the first, Rizzo is on a very team-friendly extension already. Loyalty aside, Rizzo deserves to be paid big bucks and he’ll probably wait until he’s a free agent to get it.

Taking all this information into account, in this writer’s opinion Contreras will get the first extension. His will probably be one of the cheapest and he’s already one of the best defensive catchers in baseball. Maybe a deal like Rizzo’s seven-year, $41 million? That would cover all of his arbitration years and his first two free agent years after that.

Which player do you think will get the first extension? Let us know in the comments.

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