Now 'sellers,' who will Cubs deal by Deadline?

July 9th, 2021

Just two weeks ago, the Cubs were atop the National League Central, celebrating a combined no-hitter against the World Series champion Dodgers.

Things were going well in Chicago, leading to plenty of speculation about which players Jed Hoyer should target before the Trade Deadline on July 30.

Thursday, Hoyer -- in his first year as the Cubs’ president of baseball operation -- all but declared that the club’s recent 11-game losing streak changed those July plans, putting Chicago on the path to selling rather than buying.

Sources confirmed that path on Friday, telling that the Cubs are indeed heading into sell mode, with NL All-Stars Kris Bryant and Craig Kimbrel heading the list of players who could be on their way out of town.

Bryant is headed for free agency after the season, while Kimbrel has a $16 million club option that should be picked up given his return to All-Star form this year. Add in impending free agents Anthony Rizzo, Javier Báez and Zach Davies – not to mention players with one year of control left such as Willson Contreras and Joc Pederson – and the Cubs’ roster might look dramatically different by July 31.

“We've believed in these guys since 2015. They've had a ton of success, and I would never count these guys out,” Hoyer said Thursday. “But 11 days ago we were certainly fully on the 'buy' side of these transactions, and everyone was calling about that. And obviously people are now calling to see which players are available. So, it's a very different scenario [than what] we expected. Life comes at you fast.”

Hoyer expects to be on the phone “a lot” over the next three weeks, and while he left the door open for a positive run that pulls the Cubs back into the NL Central race -- they entered Friday tied for third place at 43-45, 9 1/2 games behind the Brewers -- he admitted that the odds are becoming increasingly stacked against them.

“When you're in this moment and your playoff odds get into single digits at this time of year, you have to keep one eye on the future and think about what moves you can potentially make that can help build the next great Cubs team,” Hoyer said. “I think you have to think through those things. I think it'd be irresponsible not to take those phone calls and think through it.”

It remains to be seen what kind of assets the Cubs can land if they sell their highest-profile players. Kimbrel figures to be the most attractive trade piece; no less than a dozen contenders are in desperate need of bullpen help for the stretch run. Pair those needs with Kimbrel’s control through 2022, and he should bring back as strong a return as any player on the Cubs’ roster.

But Kimbrel might not be the only reliever on the block; Andrew Chafin and Ryan Tepera are both having strong seasons, opening the possibility for the Cubs to move all three. Chafin has a $5.25 million option for 2022 (with a $500,000 buyout), while Tepera, who is earning $800,000 this season, will be a free agent. Relievers often bring back the best return given the number of teams looking for bullpen help, opening the door for Hoyer to capitalize on that market.

“Pitching is really going to be needed down the stretch,” an American League executive said. “I see some teams trading for two or three relievers and optioning guys, resting them and being creative down the stretch. [The Cubs] can rebuild their bullpen in the offseason.”

Beyond the bullpen, Bryant figures to be a popular target for contenders given his positional flexibility. Whether it’s a team looking for corner-outfield help (Yankees, Braves) or an upgrade at third base (Mets, Brewers, Nationals), Bryant could help fill that need.

Báez joins Trevor Story as star rental shortstops, though as we saw with Manny Machado a few years ago, finding a match for such a deal can be tricky. Not only does a team need to be in the market for a shortstop -- think the Athletics, for example -- but it also must be willing and able to take on salary. Story will be owed about $6 million over the final two months of the season, while Báez will earn less than $4 million, something that might work in the Cubs’ favor.

Rizzo will be owed roughly $5 million for the final two months of the season, and while first base isn’t a major issue for most contenders, two AL East rivals -- the Yankees and Red Sox -- could be in play for the 31-year-old.

Although payroll certainly played a role in the offseason trade of Yu Darvish to the Padres, Cubs president of business operations Crane Kenney said last month that “finances won’t be the issue at the Deadline.” If Chicago plans to contend in the next year or two rather than diving into another full tear-down like we saw in 2012, paying down some of these salaries would enhance the returns in these trades.

“We're in a different situation now than we were in 2012,” Hoyer said. “We are going to have roster turnover. We need to do that. That was inevitable. You control guys for six or seven years. It doesn't last forever, as far as that initial club control. So, we'll have turnover. But this is certainly not a rebuild by any kind of definition from our past.”

Who else could be on the block in the coming weeks?

Davies will be a free agent after the season and would provide a contender with a good, mid-rotation arm, while Pederson -- who has a $10 million mutual option for 2022 with a $2.5 million buyout -- could be a fit for a team looking for a lefty bat in the outfield.

Contreras is arbitration-eligible for one more year, but he would be a more likely offseason trade candidate, as contenders rarely deal for a starting catcher this late in a season.

Whatever happens during the next three weeks, Hoyer and the Cubs appear to be more focused on 2022 and beyond than they are on the current season, one which unraveled as quickly as any we’ve seen in a while.

“We've seen what it looks like to win 100 games, win 97 games, win the division; right now, we're obviously not doing that,” Hoyer said. “Starting with me and then working down, we have to build a roster that I feel like goes into the season as the favorite year after year. In doing that, it's going to take some turnover to do that.”