Cubs: New free agent rankings leave us asking ‘what might have been’

Opening Day this year will feel wildly different than any we’ve experienced in some time as Cubs fans. You’ll see the Kris Bryant, Anthony Rizzo and Javier Baez jerseys in the seats – but odds are, all three will be opening the season in their respective new homes.

Baez already has a new team, the up-and-coming Detroit Tigers, who inked the former All-Star infielders to a six-year, $140 million deal early in the offseason. The lockout has kept both Bryant and Rizzo from signing anywhere – and, according to the latest free agent rankings from The Athletic (subscription required), both are likely to be hot commodities when business resumes.

Jim Bowden took a crack at ranking the top 70 remaining free agents – and a trio of former Cubs, including Bryant (4) and Rizzo (10) can be found in the top 10. Nick Castellanos occupies the #5 spot on the list – and looking back on the last few years, you can’t help but wonder ‘what might have been’ had things gone differently on the North Side.

Before we delve too deeply into that – keep in mind those aren’t the only former Cubs on the list, with another ten showing up, meaning that nearly one-in-five of these players have played for Chicago.

• Kyle Schwarber (12)
• Jorge Soler (18)
• Ryan Tepera (24)
• Andrew Chafin (27)
• Joc Pederson (29)
• Steve Cishek (40)
• Matt Duffy (47)
• Brett Anderson (48)
• Zach Davies (49)
• Drew Smyly (50)

Now, that’s not to say all these individuals made a positive impact on the club – or, at least, not the impact we’d hoped for. Seriously, I’d buried the Brett Anderson fiasco deep, deep down and had successfully done so till reading that piece in The Athletic. But the point still stands – the Cubs got that championship, yes, but fell well short of the expectations we all had back in 2015 and 2016.

Chicago Cubs: Had things gone differently, we could be talking dynasty

First and foremost, extending any of the Baez-Rizzo-Bryant trio could have drastically altered the franchise. Failing to do so will continue to be re-hashed by fans on bar stools for years to come – and rightfully so. It might end up being the right call, but, at least last summer, was still a very bitter pill for us all to swallow.

Soler never really panned out – only reaching his potential with the Royals and, then again, late last year with Atlanta. Schwarber got dumped coming out of 2020, then had a monster showing last year between Boston and Washington. There’s a chance Tepera and/or Chafin come back in free agency this offseason – and then, obviously, as you get further down the list, the impact those guys have had in their careers in general, wanes.

Castellanos is still a sore spot with Cubs fans, who were irked watching the slugger go on an otherworldly tear after joining the team in 2019 only to join the division rival Reds in free agency, with the Cubs a total non-factor in his market. It’s worth wondering if his bat in the mix makes a difference in 2020 or 2021, perhaps giving Chicago one last chance at a ‘Last Dance’-type scenario.

All that’s in the past, now, though. Eyes forward. It’s, once again, about prospects and up-and-comers in Wrigleyville. Hopefully, sooner rather than later, we’re talking World Series expectations again.