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Two months ago, I was sitting here writing about the Cubs closing the book on the best era in franchise history. The dust has settled, the ship has sailed, etc. That era is over. In terms of moving forward and hoping to open the window of contention as soon as possible this time around, the first order of business for president of baseball operations Jed Hoyer would be to evaluate what remains after the post-trade deadline sell-off.

A casual first glance says things have gone horribly. The Cubs are 17-35 since July 29. They lost 12 in a row at one point and have currently lost six straight, 10 of 11 and 13 of 15. There was competent play prior to this awful recent stretch, though. They were 11-4 from Aug. 23 through Sept. 8. Overall, though, the wins and losses mean a lot less than individual performances right now.

There are several players who have established that they should get a chance to stick around. 

  • Frank Schwindel is at the top of the list. The 29-year-old former career minor-leaguer has now appeared in 50 games for the Cubs. He's hit .352/.398/.643 with 16 doubles and 13 homers in 211 plate appearances. 
  • Rafael Ortega has hit .283/.347/.453 (114 OPS+) in his 305 plate appearances. Even if the Cubs don't want to go into next year with him as an everyday starter, he's a keeper in terms of a roster spot. 
  • Due to the 153 strikeouts in 338 at-bats and .231 batting average, Patrick Wisdom shouldn't be a middle-order hitter (maybe somewhere around the seven hole?) on a contender, but he's hit 28 homers in those part-time at-bats and is worthy of being a starter. 
  • In his last 35 games, Ian Happ has hit .346/.400/.709. He was good in 2019-20 and won't be too expensive in arbitration. He's worth keeping around. 
  • Willson Contreras has established himself as a catcher who can play at an All-Star level, will be inconsistent at times, but with a floor that is still above average. 
  • Nico Hoerner at some point needs to prove he can stay healthy and the lack of power is worrisome (.369 SLG), but he's a contact hitter with a .300-plus batting average. 
  • Nick Madrigal was acquired at the trade deadline and is out for the season, but he's a career .317 hitter in 303 at-bats. 

Right there are seven position players that could be part of of a contending team. Perhaps Alfonso Rivas and Michael Hermosillo are part of the mix as well. Robinson Chirinos works as a backup catcher if they wish to retain him as well. 

The thing the above group is missing is a star or two. Hold that thought for a moment. 

The bullpen has enough live arms that it might actually be OK, despite the numbers looking ugly in the second half. Adbert Alzolay's move to relief should remain permanent and he has great potential there as he's shown in his seven outings this month (1.56 ERA, 19 strikeouts, one walk, 17 1/3 innings). If Keegan Thompson and/or Justin Steele aren't in the rotation, they have nice upside. Rowan Wick and Brad Wieck will be back. Adam Morgan is a capable lefty. Codi Heuer came in the deal with Madrigal and has generally been good. Manuel Rodriguez has huge upside. There have been meltdowns, but there's real talent in this group. 

In fact, Andrew Chafin and Ryan Tepera (relievers the Cubs traded in July) are good illustrations of Hoyer's ability to grab bullpen arms on the cheap and find success. 

All this is to say I don't think grabbing any big-name relievers in the offseason is a good plan. Instead, Hoyer should focus on the rotation and at least one marquee position player. 

Speaking of the rotation, it looks to be in dreadful shape for next season. Kyle Hendricks has taken a big step back in 2021. He can have good outings and is worth a rotation spot, but he shouldn't be slotted as a No. 1, No. 2 or even No. 3. We could mention Alec Mills in similar terms. Maybe Thompson or Steele work. There aren't any others in the upper levels of the minors ready to jump into a contending rotation. 

That means Hoyer is left looking outside the organization. 

Hoyer recently said the Cubs plan to be "really active" in free agency. Baseball-Reference estimates through arbitration raises and pre-arbitration cases the Cubs payroll for 2022 is right now estimated at $79.1 million. They were up over $220 million in 2019. Yes, we know owner Tom Ricketts talked about "biblical" financial "losses" with no fans in 2020, so it's entirely possible they won't allow Hoyer to come close to that figure, but seeing half-empty stands since the trade deadline instead of full capacity has to motivate ownership to once again put a product on the field that will pack Wrigley and keep those dollars streaming in. 

To be clear, this means it's plausible to see the Cubs adding some serious beef to the payroll for next season. Maybe $100 million. Maybe even more. 

That should come in the form of at least one and maybe two needle-movers on offense and at least two viable starting pitchers, preferably frontline types. 

A reunion with Javier Bàez could work, but Corey Seager, Carlos Correa, Trevor Story and Marcus Semien are also out there. Speaking of reunions, look at outfielders Nick Castellanos and Jorge Soler ready to hit the open market. Just two of these names (Seager and Castellanos?) with the seven position players listed above has the makings of a quality offense. (And, no, I don't think Kris Bryant and/or Anthony Rizzo reunions are on the table, for those curious).

As for the rotation, something like Marcus Stroman and Robbie Ray would be great. Kevin Gausman, Dylan Bundy, Steven Matz, James Paxton, Carlos Rodón, Noah Syndergaard and lots of other interesting names are out there as well. 

Regardless, the Cubs have the financial wherewithal to be major players in the offseason and if everything breaks right, they'll be right back in the NL Central mix in 2022. They have a decent enough supporting cast in place. It's time to buy the stars. It's up to Hoyer to identify which ones work and lure them in.