The Chicago Cubs finally won the World Series in 2016. And by looking at their roster, it sure looks like they can turn right around and win another in 2017.

So, they might as well set their sights on the more distant future—specifically on how long they can keep Kris Bryant around with a contract extension worthy of his talents.

The Cubs don’t need their star third baseman to prove anything else. All he’s done in the last four years is make everyone else look bad. Bryant was Baseball America‘s College Player of the Year and the No. 2 pick in the draft in 2013. He was the Minor League Player of the Year in 2014. He was the National League Rookie of the Year in 2015. This year, he was the NL MVP and a World Series champion.

Bryant already owns a .900 career OPS with 65 home runs and 21 stolen bases. The 24-year-old has been one of the most valuable players in baseball since 2015. He also holds a special place in the wins above replacement rankings for third basemen through two seasons:

  1. Kris Bryant: 13.6
  2. Evan Longoria: 11.8
  3. Wade Boggs: 11.7
  4. Eddie Mathews: 10.6
  5. Art Devlin: 8.9

At the risk of stating the obvious, here goes nothing: Bryant is not only the best player on the Cubs but just the kind of player they should want as their franchise cornerstone.

There’s no hurry for the Cubs to extend Bryant. He’s not arbitration-eligible until 2018. And thanks to some shady service-time manipulation, Bryant’s not due for free agency until after the 2021 season.

But if nothing else, starting extension talks with Bryant would be a much-needed show of good faith by Chicago.

Though the Cubs were within their rights to keep him in the minors at the start of 2015 and thus extend his club control from six years to seven, Bryant and agent Scott Boras were miffed about it enough to file a grievance.

This spring, Bryant played the good soldier but also let slip his hope that baseball’s next collective bargaining agreement would open a window for him to hit free agency earlier.

“I don’t know if I should speak on any of that, just because I’m still young,” he told Patrick Mooney of CSN Chicago in mid-March. “I’m still trying to figure out the process of how things work. And if that happens, that would be great.”

Bryant didn’t get his wish, as Mark Gonzales of the Chicago Tribune reported Dec. 2 that the new CBA did nothing to alter his situation. Regardless, it may not be long before he becomes considerably less amenable to signing an extension.

He is, after all, a Boras client. Such players have generally been exempt from the recent trend of teams locking up their homegrown stars with big extensions. Boras‘ preference is to take his guys to free agency, where the prices are higher.

And right now, the going rate for superstar free agents is close to skyrocketing.

It’s all about the 2018-19 offseason. That’s when Bryce Harper, Manny Machado, Josh Donaldson and other notables are due for free agency. The biggest contracts in baseball are worth around $25 million to $30 million per year. The 2018-19 offseason could boost that figure to $35 million to $40 million per year.

Once Bryant and Boras see such figures with Bryant only three years from his turn, there will be little chance they settle for a more team-friendly offer from the Cubs.

Now is just the right time for such an offer.

A ton of money will come off the Cubs’ books after 2017. Also, the short distance between Bryant and his arbitration eligibility and the long distance between him and his free agency could make him willing to trade long-term earning power for immediate financial security.

The most obvious comparison to Bryant’s situation is the one that preceded Mike Trout’s signing a six-year, $144.5 million contract with the Los Angeles Angels in 2014.

That was not only a case of an elite young player who signed for big money, but Trout was also fresh off his first two full seasons and heading into his final pre-arbitration season. His extension bought out all three of his arbitration years and three free-agent seasons.

The money in Trout’s deal ($24.1 million per year) is close to what Bryant and the Cubs could agree on. The difference is that he’s older now than Trout was in 2014, which raises complications.

If Bryant were to sign a six-year contract that started in his first arbitration year in 2018, he’d be giving away only two free-agent years but also setting himself up to hit the market after his age-31 season in 2023. That’s older than most teams like their free agents, which won’t be lost on Boras.

The Cubs could settle for buying only one year of Bryant’s free agency, of course. But if they’re going to spend big on him this early, they’ll want to ensure they get him for more than just one year longer than they’re projected to. And since he’s so far from free agency at this point, there’s also the question of why the man himself would give up any free-agent years.

The best way around these issues? How about copying what the Miami Marlins did with Giancarlo Stanton?

The 13-year, $325 million contract Stanton signed in 2015 is known for being the largest in professional sports history. But due to the opt-out after 2020, it’s really a six-year, $107 million contract with a seven-year, $218 million option. It will be a huge payday if Stanton serves the whole thing, but he has a window to even more riches if they’re there for the taking.

Mind you, the Cubs couldn’t get away with back-loading a similar deal as much as the Marlins did. Bryant’s too good for that.

“Stanton is great, but for me, I’d rather have Bryant over any player in the game not named Mike Trout,” one NL executive told John Perrotto of FanRag Sports in November.

But if the Cubs offered, say, $25 million per year for six years with an opt-out after 2023 and $30 million-plus per year afterward, they could soon have Bryant’s signature on the dotted line. Such a deal would up the ante on the biggest contract in history and also give Bryant a chance to earn even more money.

Whether it’s a shorter deal or a longer deal with an escape hatch, the numbers in any extension for Bryant are going to be either big or bigger. This is what he’s earned after establishing himself as such a special talent, and the Cubs should be more than happy to oblige him.

If this isn’t already a top priority, it should be sooner rather than later.


Stats courtesy of and FanGraphs unless otherwise noted/linked. Contract and payroll data courtesy of Cot’s Baseball Contracts.

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