If general managers of baseball teams still used paper calendars and magic markers, they would have circled those calendars years ago, drooling with anticipation for this winter. Bryce Harper and Manny Machado are multi-tool superstars in their mid-20s, making them the kind of ultra-rare players who could smash the all-time record for biggest contracts in baseball history.
The bad news is that 28 (or maybe 29!) teams will lose out on the Harper and Machado sweepstakes, leaving a lot of disappointed shoppers … or, let's be honest, a handful of disappointed shoppers, and an avalanche of teams that wouldn't spend $350 million-$400 million on one player if the world were about to end.
That got us wondering: What will be the next mega-class for free agents? Which market projects to generate bidding frenzies for multiple players, maybe even eclipsing a 2018-2019 class that, aside from the top two, looks like a dud?
You can find marquee potential free agents in each of the next five free-agent classes, to be sure. If you're the impatient type, dive right in next winter for Nolan Arenado, Paul Goldschmidt, Anthony Rendon, Chris Sale, Gerrit Cole and Xander Bogaerts. The Class of 2022 could be a banger, with Aaron Judge, Alex Bregman, Trea Turner, Andrew Benintendi, 2018 Cy Young winner Blake Snell and 2018 MVP winner Christian Yelich leading the charge. Even further out, Jose Ramirez and Cody Bellinger headline a Class of 2023 that could fill up with stars as some of the most promising youngsters in today's game enter their prime. It's tempting to give the title to the Class of 2020, since 2018 AL MVP Mookie Betts will hit the market just after his 28th birthday … and even he will take a back seat to the best player on Earth, Mike Trout.
With due respect to all those classes, there's one winter that could bring both gigantic top-of-the-board deals and one of the widest array of stars in the nearly half-century since Andy Messersmith and Dave McNally ushered in the free-agent era.
It's the Class of 2021. The Year of the Shortstop.
The Class of 2021 features three Rookie of the Year winners, one MVP winner, and a slew of All-Star appearances, Gold Gloves, and Silver Slugger awards. But as the market for Harper and Machado will demonstrate (and as the market for other young free agents like Alex Rodriguez and Jason Heyward has taught us in the past), upside means everything in free agency.
Baseball's increasingly shrewd and risk-averse group of general managers don't want to pay for past results. They want to pay for future potential. That means finding free agents who exhibit the rare combination of proven results, excellent health, and the kind of youth that's tough to find, with most first-time free agents coming out in their late 20s, or even their early 30s.