In a recent post on ESPN.com, Dan Szymborski hailed MLB’s current crop of shortstops as quite possibly the best the sport has ever seen (Insider access required). Citing projected WAR over the next 10 years, there are currently 16 shortstops who could put up 20+ WAR over the next decade. If we dial it back to last year, there were still 14 such studs.

The next-best class on the list hailed from 2001-10 and included Derek Jeter, Miguel Tejada, and Jimmy Rollins, among others. They had nine 20-WAR players. And the 1987-96 group featuring Hall of Famers Cal Ripken Jr., Barry Larkin, and Ozzie Smith? They had eight.

Before we go further, let’s provide a little more context for this whole deal:

Don’t take my word for it, however. Let’s run down the data. Looking at the ZiPS projections for the next 10 years at the shortstop position, there are a shocking 16 shortstops in professional baseball projected with an over/under of 20 WAR over the next decade. Now, 16 players’ being projected to have an over/under of 20 WAR at shortstop doesn’t mean that 16 players will. As a group, players don’t exactly match their midpoint projections. Some will overperform, some will underperform, and some will move off the position. A Monte Carlo simulation with the year-to-year probabilities for all shortstops in baseball can guess how many players will hit this mark. As for moves to other positions, ZiPS contains a model for the probability that a player moves to a less strenuous defensive position (a combination of defensive performance, age and size works the best). Even running the projections in this manner, 16 players, on average, are projected to end up with 20 WAR as shortstops. There are enough players close to the 20-WAR mark to balance out the players who will underperform or move to third base or elsewhere before the decade is done (of the list of 16, ZiPS sees Seager and Correa as the most likely to move at some point).

The player on this list with whom I’m guessing CI readers will be most interested is Addison Russell, who projects to compile 39.5 wins above replacement over the next 10 years. That’s strong. It’s also only the fourth-highest total of a roster that boasts Carlos Correa (49.9), Francisco Lindor (49.5), and Corey Seager (42.6). And Russell’s even got some competition from NL Central rivals Aledmys Diaz (23.3) and Orlando Arcia (21.8).

So, looking at projections and seeing how great Russell might be is fun and all, but there’s a very practical application for the rankings as well. Remember last week when we talked about the Cubs getting nowhere on extensions for their young players and how that was tied to market-setters like Manny Machado and Bryce Harper hitting free agency this winter?

That’s the macro view, but there’s also a pecking order of sorts when it comes to elite players at the same position, particularly when they’re in similar FA classes. And wouldn’t you know it, all four of the top projected-WAR players on Szymborski’s list are set to hit free agency in the same year. It’s unlikely all will actually hit the market in 2022, but they wield significant power as individuals and as a group, leverage they’re not going to give up for less than a king’s ransom.

Lindor has already turned down what was reported to be “a package around $100 million” and Correa’s agent said his client “is never going to do a(n early) multiyear contract.” While the player himself walked that back a bit and said he’s willing to listen to the right offer, he also said that he’s unwilling to talk about a long-term deal once he hits his arbitration years. Wait, what does this have to do with Russell?

While every player and organization are different, and thus have varying motivations and valuations based on their circumstances, you have to think both the Cubs and Russell’s camp are keeping a close eye on developments with the other shortstops. It’s like a game of chicken in which both sides are trying to time the market just right in order to get the best deal. And what is that number in this case?

Len Kasper called Russell a “future MVP” when presenting him during the ring ceremony earlier this month and all signs point toward him becoming an elite producer both offensively and defensively. Depending on where the average annual value for true superstar-caliber players heads after this season, it’s not unreasonable to imagine the Cubs shortstop commanding $30 million per.

That’s pretty much right in line with the idea that an incremental win is worth roughly $8 million, which means Russell’s projection says he should be “worth” about $31.6 million AAV over the next decade. Cool, so the Cubs should just offer him a 10-year, $320 million deal, right? Huh, no, I don’t think it’ll work that way, not when they’re getting him for well under a million this year and will only have to deal with arb raises starting next year.

But what about a seven-year, $120 million deal? That would buy out his arb seasons and three years of free agency, which could be worth $90 million based on our rough assumptions here. Would the remaining $30 million over the next four seasons ($7.5M AAV) be enough to entice Russell to opt for free agency as a 31-year-old rather than a 28-year-old? Because these contracts cut both ways, you know.

There’s something to be said for the time value of money and the immediate security of having much bigger paydays now, but you could be forfeiting the opportunity for even bigger numbers by not hitting the market as early as possible. And Russell is represented by Scott Boras, who isn’t exactly known for being a softy who’s all about those hometown discounts. He’s going to do what’s best for his clients, whatever that might be in his mind for the given player.

Oh, look at me, I’ve gone and jumped into these cold speculative waters again. While it wasn’t my intent to do so, I suppose this provides food for thought when it comes to what the Cubs might be willing to offer and what Russell would be willing to accept. The key is whether and when those ends intersect.

For now, though, we get to enjoy watching this renaissance of sorts on the left side of the infield as a gaggle of uber-talented youngsters usher in a new age for the shortstop position. That alone is worth its weight in gold, just as these various players will be when it comes time to sign new deals.