Thoughts on a flop of a Cubs trade deadline

I’ve been chewing on this one for weeks.

I’ve been looking for silver linings from the beginning of this month but sadly, dear reader, I keep coming up empty.

In the moments where I’ve done the best mental gymnastics, I’ve been able to celebrate the David Robertson trade that netted the Cubs Ben Brown, who despite a brutal second start at Tennessee, is right there in the argument with Cade Horton, Jordan Wicks, Jackson Farris, DJ Herz, and Caleb Kilian to be the Cubs’ best pitching prospect. I’ve also twisted my brain into a pretzel, enjoying the conversion of Scott Effross from a late-emerging reliever into likely future starter Hayden Wesneski, whose starts at Iowa have gone from disastrous to bad to superb.

Unfortunately, I just can’t get over how the Cubs handled the Willson Contreras situation.

With any player heading toward free agency, clubs have three options for how to handle the player. The club can (1) extend him, (2) trade him, or (3) play out the string and lose him for pennies on the dollar. Option 1 is beneficial from a continuity and leadership standpoint, and option 2 is preferable when a club isn’t heading for the postseason that year or the next. We rightly ridicule clubs who choose option 3. The Rockies famously did this with Trevor Story last year and were rightly pilloried by the baseball community. Then, incredibly, they did the same thing with Daniel Bard this year (technically, they did extend him, but extending a reliever in his mid-30s is a shameful decision for a last-place team).

At least the Rockies got a competitive balance round A pick when Story left; that pick turned out to be 31st overall. In contrast, due to their market size, the Cubs would receive a pick the the 75th to 80th neighborhood. For reference, the assigned pick value for the compensatory picks awarded to teams like the Rockies averaged $2.4 million in 2022 whereas the average pick value for compensatory picks awarded to teams like the Cubs is just a hair over $840,000.

How excited are you about the notion of the Cubs trading Contreras straight up for Christopher Paciolla? Paciolla was the Cubs’ pick at 86th overall this summer and signed for $900,000. That’s what the Cubs can expect if Contreras walks as a free agent, and that’s assuming that he signs in the offseason. Should the Cubs find themselves in a Craig Kimbrel situation, they could get nothing even if Contreras walks in free agency.

The Cubs made their decision with Contreras years ago. According to Jesse Rogers, the Cubs haven’t had extension discussions with Contreras since 2017. Strike option 1. Thus, the Cubs decided that they would either trade Contreras or let him walk, and as we discussed above, letting him walk is a nightmarish decision from an asset management standpoint.

Yet here we are. After all of the tears and the strife, the Cubs find themselves staring down an offseason in which they will either owe him a market-rate contract or permit him to join another team for precious little compensation.

Let’s briefly revisit deals that even appeared underwhelming at the time to appreciate just how much more valuable it is to trade a player at the deadline. Remember when the Cubs sent Kris Bryant to the Giants and only got back Caleb Kilian and Alexander Canario? Kilian now finds himself a likely long-term rotation member and Canario just punched his ticket to Triple-A Iowa after fully realizing his power potential this year to the tune of 31 homers across High-A and Double-A in just 105 games. He’s a real prospect now. Remember when Craig Kimbrel netted an injured bat-only second baseman with no power? Well, Nick Madrigal is back hitting .327 with a .411 on-base percentage after returning from injury. He’s establishing himself as a real Major Leaguer. Remember when the Cubs sent Andrew Chafin to the A’s for Greg Deichmann? Well, Deichmann flopped, posted a wRC+ of just 60 at Triple-A and was released the other day. Drat. But what about the other guy? That’s Daniel Palencia. If you haven’t seen Palencia before, spend a minute on this thread. Palencia is undersized, but he throws 100+ and uses a low-90s slider and his changeup in games, yielding a strikeout rate of nearly 12 strikeouts per nine innings at High-A.

I can’t believe I have to make this point, but this is why sellers make deadline deals. Even when they don’t think the deal is a huge win — we surely all hoped for a name like Marco Luciano, Luis Matos, or Joey Bart in the Bryant trade, right? — it turns out that scouting players in the mid-minors has a far higher success rate than scouting teens and collegiate ballplayers.

I’ve gotten this far and haven’t even mentioned Pete Crow-Armstrong or Kevin Alcantara. And that’s the point. That’s because you don’t need to get a potential star to make a good deal.

But getting only a compensatory draft pick for Contreras or keeping him with a market-rate deal is a terribly bad decision.

We haven’t yet mentioned the fact that Ian Happ was an All-Star this year after struggling through a mediocre 2021 season. Whereas Contreras was highly likely to produce in his walk year, Happ was far from certain to do so. And yet, here we are in late August with Happ still on the team.

I like both of Contreras and Happ. Simultaneously, I don’t understand the asset management play in keeping both of them past the deadline.

I’m not moved by the argument that perhaps the offers weren’t there. Trading is like college football recruiting. You don’t win by recruiting the guys that want to come to your school; you win by recruiting the best players and convincing them to come to your school. In much the same way, the best trade haul should be generated by you convincing an opposing general manager that he or she desperately needs what you’re selling. If Jed Hoyer and/or Carter Hawkins can’t get that job done, perhaps someone else needs to be empowered to try.

For the next six weeks, I’ll get tremendous satisfaction out of watching Contreras and Happ play ball. But I’ll be scratching my head at the same time, and it’s only going to get worse come November.