Offseason Questions For The Cubs (www.mlb.com)

CHICAGO — The Cubs had hoped to be able to hand the ball to Jon Lester during the Wild Card Series against the Marlins in October. That did not happen, and the veteran lefty understood fully that his time with the franchise might have expired.
“If this is it here,

CHICAGO — The Cubs had hoped to be able to hand the ball to Jon Lester during the Wild Card Series against the Marlins in October. That did not happen, and the veteran lefty understood fully that his time with the franchise might have expired.

“If this is it here, this is it. I have to move on with it,” Lester said in his final press conference. “I’ve definitely appreciated everything that this organization has done for me.”

Earlier this week it was reported that Lester reached a one-year contract with the Nationals, who also signed former Cubs outfielder Kyle Schwarber this offseason. Lester will be reunited with manager Dave Martinez and pitching coach Jim Hickey — both former members of the Cubs’ staff — rather than return to the North Side.

Lester’s legacy in Chicago is secure, though. He helped change the culture with his arrival in 2015, reached October five times in six years and won a World Series in 2016. All he did in that Fall Classic against Cleveland was pitch in Games 1, 5 and 7, and he will forever be a legend among the Cubs’ faithful.

But his exit via free agency only emphasized Chicago’s ongoing need for rotation help and depth, as did the recent deals reportedly struck by Tyler Chatwood (Blue Jays) and José Quintana (Angels).

With that in mind, here are three questions facing the Cubs.

1. Should the Cubs have re-signed one of Lester, Chatwood or Quintana?

Of those three, Chatwood looked like the best option to try to bring back. Without Yu Darvish, the rotation has three finesse starters leading the way in Kyle Hendricks, Zach Davies and Alec Mills. If healthy, Chatwood would have added velocity to the mix.

Beyond that, Chatwood spent much of the last few seasons as a swing man. He thrived in that role in his solid bounceback campaign in ’19. Looking ahead to ’21, the Cubs need innings and versatility and depth, and Chatwood might have been able to offer precisely those in some shape or form.

That said, Lester still showed in ’20 that he could eat innings, and he was the sentimental favorite to return.

The veteran leader — unquestionably one of the great free-agent signings in Chicago sports history — wanted to come back and try to win his 200th career game while wearing a Cubs uniform. Though the Cubs said from the final day of the ’20 season that there was mutual interest, all that talk did not bring on a reunion, a disappointing development for plenty of fans.

Neither Lester (inked to a one-year deal worth a reported $2 million in ’21, with a $3 million signing bonus to be paid in ’23) nor Chatwood (reportedly one year for $3 million, plus incentives) cost all that much, relatively speaking. It was another reminder that Chicago appears to be searching for options on a budget.

2. What realistic rotation options still exist on the free-agent market?

Where does that leave the Cubs? Well, it leaves them with at least one hole, and as many as two, in the rotation. It leaves them still with further depth needs behind the Major League cast, too.

Yes, there should be opportunities for such young internal options as Adbert Alzolay, Cory Abbott, Tyson Miller, Justin Steele and Brailyn Marquez, among others, in ’21. Rule 5 pick Gray Fenter and righty Duane Underwood Jr. will also be stretched out and looked at as rotation depth options, and the Cubs will look for reclamation projects (like the reported recent addition of Shelby Miller as a non-roster invitee).

Still, the Cubs need some more experienced Major League innings.

Given the way the offseason has played out for the North Siders, free-agent possibilities could include Chris Archer. Archer missed all of 2020 due to thoracic outlet syndrome, but he hopes to be ready to go by Spring Training. Free agents Mike Foltynewicz, Carlos Rodón, Rick Porcello and Trevor Williams are coming off forgettable ’20 seasons but might benefit from the Cubs’ analytics team.

Or, hey, if the Cubs want to stick with “veteran left-hander with leadership qualities” in the wake of Lester’s departure, 40-year-old Rich Hill is on the open market, too. Hill, who made his big league debut with the Cubs back in 2005, is coming off a one-year, $3 million (before prorated) pact with the Twins.

3. Don’t the Cubs still need a backup catcher?

Indeed, these pitchers will need someone behind the plate on the days Willson Contreras is not catching — and that’s if all those trade rumors surrounding Contreras this winter turn out to be more smoke than fire.

President of baseball operations Jed Hoyer has said that top catching prospect Miguel Amaya is not ready for the No. 2 job. Chicago still needs to land a backup for the big leagues after sending Victor Caratini to the Padres as part of the Darvish deal.

The left-handed-hitting Jason Castro looked like a solid possibility, but he has reportedly signed a two-year contract with the Astros. If the Cubs want a lefty bat or a switch hitter, options still on the open market include Alex Avila, Matt Wieters and Tony Wolters. Tyler Flowers — known for his excellent framing — is also out there.

Jordan Bastian covers the Cubs for MLB.com. He previously covered the Indians from 2011-18 and the Blue Jays from 2006-10. Read his blog, Major League Bastian and follow him on Twitter @MLBastian.



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