Which Cubs players make sense regarding extension talk?

Baseball super-agent Scott Boras had his periodic and unrequested "state of baseball finances” talk last week. Unsurprisingly, Kris Bryant and his Cubs future came up in the discussion. With Bryant and a few other Cubs on the verge of free agency, players getting extensions has been a bit of a topic. Which current Cubs players make the most sense for an extension?

In the Theo Epstein years, four players received long-term extensions: Kyle Hendricks, David Bote, Starlin Castro and Anthony Rizzo. For an extension to make sense, a few factors need to align. The player should have displayed long-term potential, but he also likely has to settle for less than a maximum-value return. While some super-elite players, such as Mookie Betts, don't appear to leave much on the table, the Dodgers didn't want to risk it. As much as fans might object, every fly-over state team seems to have a specific (though unannounced) budget limit. $100 million spent on one player is $100 million unlikely available for others. To fail to grasp that the Jason Heyward contract has limited some recent moves is a failure to have paid attention.

Regarding Bryant, by the time he reached arbitration eligibility, he had a Rookie of the Year and MVP Award. He had no need to settle. When Rizzo signed his, and especially with Bote, the “security” angle weighed heavily. To find the next candidate, the downside has to be as evident as the upside. By now, Javier Baez and Willson Contreras have enough league-wide respect and cash in the bank to be willing to face a season or two of uncertainty.

Ian Happ jumps off the page. Recently, I read an online comment criticizing Happ as the Cubs primary leadoff option. Whether you dig Happ as a top-of-the-order guy or not, enough downside risk is present for the 2015 first-round pick from the University of Cincinnati to at least contemplate how a restructuring might be accomplished. Equalize his pre-free agency seasons, tack on a few years after at an extended rate, and re-jigger the numbers again. It makes sense, but only because the possibility of backsliding and excelling are both present.

By the time free agency looms, negotiating an extension is usually too late. As much as we dig specific members of the Cubs, and the players have become a part of us, they want to get paid. Jeff Samardzija wanted to get paid. Since he didn't sign a team-tolerable extension, he was sent to the Athletics for Addison Russell and others. Players who head to free agency usually garner their former team nothing on the way out the door, and losing quality for nothing hinders the continuation of organic success. Which players have enough potential variance to accept an extension?

Brailyn Marquez would be an interesting one. As hard as he throws, injury concerns will be a concern. If he would consider a middle-ish figure over the next eight or nine seasons, the lefty from the Dominican Republic, who signed with the Cubs for a $600,000 bonus, could get some cost certainty. The same could apply, on the other side of the spectrum, for Alec Mills. Mills won't be even eligible for arbitration until 2023. If he'd accept a David Bote-style extension, he could probably bank six or seven million-dollar campaigns. He made league minimum in 2020. Somewhere in between Mills and Marquez falls Adbert Alzolay. The latter signed for $10,000.

No, Mills, Alzolay and Marquez aren't the names people want to talk about regarding extensions. That the Cubs have so few valid players eligible for extension talks is a sign of a recently problematic farm system. On the other hand, if a team waits until a player has fully blossomed, they might not desire an extension. As the player that everyone in the league covets is often too expensive to trade for, guessing correctly on which players will be willing to stick around an extra year or two can be mutually beneficial. At least, it's mutually beneficial at the time. A few years later, Rizzo might have unremembered his willingness to sign something the team willingly offered and he approved at the time. And perhaps shared that with his co-workers. Extensions are an ugly thing in baseball. As is anything financial.