Chicago Cubs: Five trades that could have created a dynasty
While it’s impossible to predict the future, here are five trades from the past which could have made the Cubs the dynasty we all thought they would be.
They say hindsight is 20/20. Given that the year now reads 2020, it’s apropos that we take a little gander back in time to investigate five potential trades that could have made the Cubs into the veritable dynasty we all expected them to be after the parade in November 2016. Granted, all of them would and could not have occurred in this alternate timeline, but each and every one of them would have been feasible and plausible at the specified time.
While this is an exercise in futility and tomfoolery, the fact remains that trades have the potential to happen at any time and for any reason. It also stands to reason that since these were all players who were traded at one point, the Cubs could have been players either at that point or another. Also, trades that were once thought foolish at the time they were made now look stupendous, and the inverse also holds true – that’s just the nature of trading.
Sometimes, trades are efficient and productive for both teams, as in the case of the Gleyber Torres for Aroldis Chapman deal that gave both teams exactly what they were looking for knowing all the risks and future ramifications. Cubs fans may look back on it and say they should have given up Addison Russell instead of Torres, but they probably wouldn’t have won a ring without the services of Russell at shortstop in that miraculous postseason run. Sure, it was a lot to give up at the time and in hindsight, but would any Cubs fan give up their 2016 revelries for Torres back now? Don’t answer that – there are plenty of curmudgeons out there.
A sure thing is better than a gamble in the business world and professional sports, but gambling can often be more fun and exciting – and isn’t that what a lot of trades are at their core? In that vein, here’s a look at five prospective deals from seasons past – each of which could have extended the Cubs “window of opportunity”/playoff run and created a true Cubs dynasty.
Chicago Cubs: Love him or hate him, he would have made the Cubs better
The scary part about many of the trades you’re going to read about in the next few minutes is that they were all possible for the Cubs. In all cases, the guys targeted here were guys the Cubs either did pursue or could have pursued with relative ease. In some cases, the desire wasn’t strong enough, in others the trade would have been difficult to swing with prospects or MLB players. Still, in others, it was just a question of money. Sound like anything you’ve heard the last couple offseasons? Yea… thought so.
First off in our potential trades that could have been is a guy who became a 2017 World Champion during the Cubs victory lap tour that has since become known as a serious World Series hangover. Funny enough, this is a guy the Cubs were supposedly interested in at the trade deadline. Guess why he didn’t come to the Cubs? I’ll even give you three guesses…
Money. Money. More money. Justin Verlander made too much money. While his new club has been a bit tarnished of late, Verlander supposedly liked the idea of being traded to the Cubs rather than the Astros in August 2017. It was reported that Verlander was willing to drop his no-trade clause and held out on his clause as long as possible on the Astros deal to try to wait out the Cubs. Jed Hoyer says the Cubs were never that close, but oh boy does he regret it in hindsight.
Chicago Cubs: All smiles in Houston could have been all smiles in Chicago
Granted, there’s no guarantee that Verlander would have been the same guy with the Cubs that he became with the Astros, but imagine if the Cubs had gotten him for the 2017 playoffs and all of 2018 and he had turned back his clock in the same way. He certainly wouldn’t have looked so bad making his Cy Young speech this year.
While the Cubs had just given up Dylan Cease and Eloy Jimenez for Jose Quintana that season, they still had MLB newcomers and top prospects Ian Happ, Kyle Schwarber, Victor Caratini, Albert Almora and many of their current crop of talented prospects who were backlogged in the system a few more years.
Happ and Caratini as the basis for that deal probably gets things started in a big way, especially depending on the money the Tigers were willing to throw in at that point in time. Would the Cubs have missed those guys terribly the last two years?
This is also one of those hindsight deals that could have had ripples out across baseball rather than just specifically within the Cubs organization. If Verlander comes to the Cubs in 2017 and does what he did for Houston in Chicago, does Houston go to the World Series? Does Major League Baseball even have a huge scandal right now with the Astros? Funny how even imaginary Cub trade proposals might have saved baseball from this ugly scandal.
Chicago Cubs: Could have been the Cubs instead of the Astros
This imaginary trade might be the most difficult to sell into reality, even given hindsight, because of the fact that the Cubs would have had to convince (and maybe overpay) for a guy who pitched for a division rival. It’s hard to believe that the Cubs price wouldn’t have been substantially higher because they were also in the NL Central, but maybe the Pirates wouldn’t have cared at that point, instead looking to rebuild as much as possible while getting rid of a guy they didn’t think they’d be able to resign once he became a free agent. (They wouldn’t have)
Gerrit Cole is probably the best pitcher on the planet right now, but in Cubs lore, he will forever be remembered as the guy who got smoked in the 2015 Wild Card game (You do remember that Schwarbomb into the Allegheny, right?). And, granted, that’s a wonderful memory for Cubs fans, as it was essentially the beginning of the Cubs run to the 2016 World Series. However, it’s not really fair to Cole, as he’s become even better than he was then, and he had to go up against the greatest pitcher on the planet in 2015 in that game.
While Jake Arrieta and Schwarber may have gotten the best of Cole that day, Cole has gotten the last laugh as he was able to parlay his time with the Astros into a sparkly new $324 million contract with the Yankees this offseason.
If the Cubs could have figured out a way to make the Pirates an offer (two or three high-level or top prospects) in the offseason before the 2018 season, they would have enjoyed two seasons of ace-level Cole rather than signing Yu Darvish or Tyler Chatwood. And while Cole, like Verlander before him, may have gained something in going to the Astros, even a reasonable facsimile of his work the past two seasons would have propelled the Cubs to the playoffs in both of the last two seasons. We didn’t even talk about any financial ramifications due to the fact that Cole made less than Chatwood the last two seasons. Yikes.
Chicago Cubs: Trading for this guy may have made the offense into a juggernaut
It’s an almost impossible task being a GM in modern professional sports, but completed trades and left-on-the-table trades are one avenue where front office types must get a lot of heartburn. Looking back on some of the trades made in the last decade, it’s impossible not to point to this one as the steal of all steals. Get out your Tums and Rolaids, Jed and Theo.
When the Brewers pulled off the trade with Miami for Christian Yelich and the signing of Lorenzo Cain in one day, they shifted the balance of power in the NL Central. Instead of January 24, 2018 living in infamy for Cubs fans, it could have easily been the best trade ever made for the Cubs organization. Not only could this trade have been a great deal for the Cubs (their top 5 prospects they could have sent to the Marlins at the time were Oscar De La Cruz, Jose Albertos, Adbert Alzolay, Alex Lange, and Brendon Little), but had the Cubs gone after and procured the services of Yelich rather than the Brewers, who knows what other dominos fall in the 2018 season.
Certainly, given the way things turned out at the end of the 2018 regular season, it’s safe to say that the Cubs and Brewers would not have tied for the Central crown that season if Yelich had been traded 90 miles south of where he ended up. It’s also safe to say that the Cubs would have featured the two best players in the National League in 2018 had this come to fruition, as Yelich and Javier Baez both put up monster seasons, with only Yelich’s nuclear September separating the two.
Add Yelich to centerfield along with Kyle Schwarber and Jason Heyward and not only do you have a more potent offensive lineup, you also have a better defensive squad than the one that platooned Albert Almora and Ian Happ (who also could have been packaged as young players going back to the Marlins) for most of 2018.
It’s also likely that with Yelich under team control and on a team-friendly deal that money issues might not be such a big deal right about now. If nothing else, there certainly would have been no move for Nicholas Castellanos in 2019 and an outcry to bring him back for more money than Yelich will make going forward.
Chicago Cubs: What if the Cubs added Manny in 2018 instead of the Dodgers?
Cubs trade with Orioles ends up helping the Cubs to a World Series title. Where have I seen this story before? Oh, that’s right- Arrieta and Pedro Strop were once Orioles included in one of the better trades in Cubs history.
Well, what if I told you that this particular imaginary trade was supposedly a possibility in the offseason of 2018? Is that something you might have been interested in?
What if I told Cubs fans I could have made Addison Russell another team’s problem before the 2018 season? Is that something you might have been interested in?
What if I told you that in making this trade, the 2018 Cubs may have been able to not only withstand the injuries/loss of Kris Bryant and do more damage in the postseason?
Yeah, I thought you might be interested.
Knowing what we do in 2020 changes so many variables for the Cubs in this past trade scenario mostly because of who we could have used as trade bait with other clubs. Knowing what we did a few years ago, if Addison Russell had been traded after the 2016 World Series, Cubs fans would have stroked out and boycotted the team.
Cubs writer Tony Andracki even scoffed at the notion of trading Russell for Machado straight up. However, with the gift of hindsight, trading Russell at the height of his value right after the World Series would have been exactly what they should have done.
Chicago Cubs: This swing would have played in 2018
A deal with the our friendly trade partners, the Orioles, could have netted us Manny Machado in 2018 (and possibly even in 2017 as well). Granted, you may not care for the guy or even the way he plays, but I’d venture a guess that you like him a fair bit more than Russell now. Point taken?
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Machado, dealt to the Dodgers at the deadline in 2018, produced 6.2 fWAR for the season, and propelled the Dodgers to the World Series that season. Russell produced 1.4 fWAR for the season and ended up suspended for 40 games (partially in September of 2018 and finished in 2019) under MLB’s domestic violence policy.
What makes all this worse is what we’ve already pointed out- the fact that this trade supposedly was discussed and could have happened at some point, although no one knows how serious either side was in the talks. It was, however, serious enough for The Athletic and Ken Rosenthal to write about a possible trade at that time.
And while Machado may have only been had for a year or partial year, the added production in 2018 coupled with the jettisoning of Russell would have saved every fan some grief and shame. Who knows- the Russell situation also could have been hanging over the players and clubhouse for the last two seasons in some way, shape, or form- draining the passion and energy that the Castellanos trade seemed to bring back last August.
Chicago Cubs: Do you realize how little the Reds gave up for this guy?
On January 19, 2017, the Reds traded Dan Straily to the Marlins for Luis Castillo. Oh, and the Marlins also threw in Isaiah White and Austin Brice too! Funny thing is, Dan Straily actually pitched for the Cubs in 2014 before going to Houston and Cincinnati. To be fair, Straily wasn’t awful for the Marlins in 2017 and 2018, but he also wasn’t very good- certainly not as good as his exquisite 2016 season for the Reds.
He also wasn’t enough for the Marlins to get for Castillo, who has gone on to become a stud for the Reds. You’re telling me the Cubs didn’t have someone of Straily’s ilk to send to the Marlins in 2017 for Castillo?
Did I tell you Castillo only just turned 27 years of age and won’t be a free agent until 2024 as well? Yeah, that’s super depressing. Imagine Castillo as that cost-controlled young stud in the rotation for the Cubs for five more years. Makes guys like Alzolay, Brailyn Marquez, and Justin Steele look even more promising, right?
As with the Brewers acquisition of Yelich (again, from the Marlins), this trade especially hindered the Cubs because the real trade was made by a Central division rival. Take away Castillo from the Reds and place him on the Cubs and you kill two birds with one baseball.
In addition, as with the team friendly deal Yelich is on currently, a trade for Castillo also would have ameliorated the Cubs current financial woes and would have allowed them to spend money more efficiently in the bullpen or for a second baseman rather than for both Chatwood or Darvish. Heck, maybe if the Cubs had managed to swing a couple of these deals, they already would have extended Cole and set themselves up with a rotation of Cole, Castillo, Hendricks, Lester, and Quintana.
That’s with Yelich in the outfield too.
Hey, we can dream in the midst of a second straight boring Cubs offseason, right?
While this look into imaginary trades was inane and seemingly without any relevance, it does point to the importance of pulling off the right trades, at the right time, with the right players – and certainly does prove that one or two trades can change the course of otherwise successful or down-on-their-luck franchises. Or, you know, make a Cubs dynasty.