Cubs deadline trades have not been what Jed thinks they were

The future didn't actually get mortgaged with the 31 (mostly) bums the Cubs have traded away when they've bought since 2015

Cubs deadline trades have not been what Jed thinks they were

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With the Cubs not even bothering to invent new ways to lose games these days—they just stick to the same formula of not scoring many runs, playing crap defense and watching the bullpen crap themselves—the front office would normally find themselves deep in sell or buy conversations seven weeks before the trade deadline. Nobody in the National League has a worse record than the Cubs since April 27 (only the White Sox do in all of baseball and the margin is literally those two games last week where the Cubs came back from five run deficits to win).

But the reality is the Cubs know they can’t sell, even if they really wanted to. This was supposed to be year two of contention after the botched sell off of the World Series team, and Jed Hoyer can’t sell another one to the fans or even the Omaha Hillbillies that own the club.

So he’s going to buy to try to fill the copious number of holes in the roster that he himself built. And if the pressure to win in year four of his regime (it’s actually year five as Theo Epstein could hardly pretend to give a shit in 2020), wasn’t enough, he has the added burden of trying to ensure the Cubs are compelling enough for people to be motivated to subscribe directly to the Marquee Sports Network sometime in September when Comcast boots them off their programming menu.

Jed’s proven ability to acquire impact talent in-season is pretty limited. With the Cubs he’s only had one team where he bought at the deadline, and that was last year when he traded for Jeimer Candelario and Jose Cuas. Jeimer was fine, Cuas was—and continues to be—less than that.

Jed was the general manager of the Padres in 2010 and 2011 before he ran back to the safety of taking orders from Theo. And in those two Julys he made trades for nobody in 2010 and who can forget the 2011 deadline trade of Mike Adams to the Rangers for Robbie Erlin and Joe Wieland, followed immediately by Ryan Ludwick to Pissburgh for cash? Wow. How daring!

There is a tremendous amount of hand wringing already about this trade deadline. The Cubs’ Prospect Perverts are premptively objecting (strenuously) to the idea that any of the Cubs horde of future Hall of Fame prospects.

But Hoyer built a very mediocre big league team and the only way to turn it into something relevant is to trade for impact players because they don’t have any. So if they are going to do anything worthwhile it’s going to cost them. But that’s what you have the minor league system for. You bring some players up and you trade others. The Epstein Cubs, for all of their success didn’t do a good job of evaluating their own players with any kind of clarity. They held onto Albert Almora until long after he proved he wasn’t anything special, they completely botched the handling of Kyle Schwarber and he eventually left for nothing. For all of their first round drafting success, the only one still around is the aggressively mediocre Ian Happ.

As troubling as the complete lack of a track record that a 50-year-old man who has been working continuously in one Major League Baseball organization or another for 23 seasons has, it’s even more concerning that Hoyer appears to have such a stunning misread of the trades his boss made during his time in charge of the Cubs.

As he said earlier this week on The Score, “We do want to avoid (what happened after the 2016 World Series). We were a little bit guilty the last time of constantly making short-term deadline deals that ended up putting us in a hole.”

I don’t think that’s what happened, Jed.

From 2015 through last year, the Cubs were buyers at the deadline in seven seasons. They were sellers in the other two (2021 and 2022). During that time they made 19 July trades (well, actually 15 in July, four trades were in the short season of 2020 when the trade deadline was at the end of August) when they were clearly buyers.

Jed claims that those deals “ended up putting [them] in a hole.” But was it really the trades?

They traded away 31 players in those deals, almost all of them minor league prospects, and of those 31 only five have gone on to post career WAR of five or better.

The best player they traded was Gleyber Torres (14.9 WAR), and he was in the Aroldis Chapman trade which turned out to be pretty important in winning the World Series.

The deal where they traded away the most WAR was the next year when they traded Dylan Cease (13.0 and growing), Eloy Jimenez (5.5 and constantly wincing in pain), and two guys who never made it to the big leagues. And that trade really doesn’t qualify in Jed’s “short-term deals” since the idea behind the trade was to acquire a cost-controlled quality starter with three and a half years left on his deal since their farm system wasn’t producing any pitching. Jose Quintana was only 27 when they made the trade. Was it a good trade? Meh. It looked really bad when Quintana struggled after doing a very nice job in 2017 after the trade and Eloy looked he might be something. Cease turned into a good, but inconsistent starter, who is now thriving away from the Sox.

The one that gets kind of lost is the trade Theo made was later that month when he traded young infielders Isaac Paredes and Jeimer Candelario to the Tigers for backup catcher Alex Avila and this guy.

Justin Wilson was supposed to be a dynamic left handed reliever for the Cubs for the next several years. He was 29, had already proven to be a reliable closer and set up guy and was having a very good year for the Tigers, but he was bad in 2017 for the Cubs, pretty average in 2018 and was gone. He pitched well for the Mets immediately after he left the Cubs, which makes you wonder. So he was good immediately before and immediately after he pitched for the Cubs but not in between? Huh?

Anyway, Paredes has posted a career WAR of 7.4 for the Tigers and Rays and Jeimer has been 13.1 for the Tigers, Nats and now Reds (he did come back last year and was 0.4 for the Cubs, so there’s that. Whatever that is.)

That trade didn’t work out because Wilson didn’t work out, but the thought behind it was fine. Where were Paredes and Candelario going to play regularly with the Cubs still rolling out their still young, talented infield of Anthony Rizzo, Javier Baez, Addison Russell and Kris Bryant? We know what happened, but only July 31, 2017 nobody sweated either of those guys being traded away.

The deal wasn’t “short-sighted” it was just poorly executed.

The truth is that Jed is learning the wrong lesson from their past deadline trades. The Cubs were mostly not bold enough. Nick Castellanos for Alex Lange (1.3) and Paul Richan (0) turned out pretty well. Cole Hamels for Eddie Butler (-0.3) and Rollie Lacy (0) was a steal.

The “other” 2016 deadline deal traded away Paul Blackburn (3.1 and still pitching in the big leagues) and Dan Vogelbach (1.3 and menacing a buffet somewhere in Ontario) but returned the guy who got the single biggest out in Cubs history. That kind of seems to be the point of all of this.

The idea that the Cubs deadline traded their way into a poor farm system that needed to be rebuilt on the ashes of the World Series team is pretty fantastical.

The best players they traded away were Gleyber, Jeimer, Cease, Paredes, Eloy and Blackburn.

And they already brought Jeimer back and let him go again, and I’m pretty sure they could pretty easily reacquire Paredes (which might be a good idea), Eloy or Blackburn if they really wanted to.

I don’t think trading away the likes of Thomas Hatch, Elliot Soto, Ivan Pinyero, Matt Rose, Jhon Romero, Zach Bryant, Ronny Simon, Pedro Martinez (no, not that one), Kevin Made, Junior Lake or podcast star Zach Short ended up crippling their future.

Did trading Montgomery for the great Martin Maldonado only to trade Maldonado a few days later for Tony Kemp mortgage the future?

How about the pandemic fever dream trades for Cameron Maybin, Jose Martinez, Andrew Chafin and Josh Osich for one player to be named later each?

And how about the fact that in back to back years Theo managed to trade for a position player who went hitless for the Cubs? Maldonado was 0-for-11 in 2019 and Martinez was 0-for-21 in 2020. Put that on Theo’s Hall of Fame plaque. He traded Mike Montgomery and Pedro Martinez (no, not that one) to get two guys who combined to go 0-for-32 with 12 strikeouts and two walks.

If Jed wants to go on a little historical tour of trade deadlines past, he might just realize that they’d have been far better off to be more aggressive and be willing to part with more of their touted but inevitably flawed prospects to get proven players.

But that might cost the Cubs money, both now and in the future and as we know all too well, that’s always the thing that really curtails their ambitions.