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The 5 ridiculous trades that got the Cubs and Indians into the World Series

The Cubs and Indians are in the World Series because they did a lot of things right. They’re also there because of some deals that still haunt their trade partners.

Jamie Squire/Getty Images

The Chicago Cubs and Cleveland Indians have built World Series teams the same way that most teams have. They benefitted from high draft picks (Francisco Lindor, Kris Bryant), deadline deals (Andrew Miller, Aroldis Chapman), international successes (Danny Salazar, Jorge Soler), and players who weren’t exactly touted prospects (Willson Contreras, Ryan Merritt). They’ve both signed free agents (Jon Lester and Mike Napoli, to name two), as well, even though the Cubs probably spent more last year than the Indians will in the next decade or two.

In other words: Look at these unremarkable remarkable teams, who got here by making the roster moves other teams made, just better.

There’s another category, though, in which these two teams might lead the world. They’ve benefitted from more ridiculous trades than any franchise should possibly expect. We’re talking Ryan-for-Fregosi, Cepeda-for-Sadecki, Brock-for-Broglio, the kinds of trades that will absolutely haunt the losing team for decades.

Here are five of them. And note that we’re not even going to include all of the typical deals, like the Indians nabbing Carlos Carrasco and Michael Brantley when trading away their Cy Young pitchers, and that Yan Gomes has to be an honorable mention because of his injury-marred season. These are just the trades that looked questionable at the time, and devastating in hindsight.

5. Carlos Santana for Casey Blake

How the deal looked at the time:
Santana was a 22-year-old catcher hitting .321/.431/.568 in the California League. It’s always wise to take Cal League stats with a grain of salt, and Santana’s previous season was a dud, so it’s not like he was a top-100 super prospect. But the scouts liked him, and the numbers sure came around.

Blake was a steady 34-year-old contributor, good for about two or three wins above replacement every danged year. Still, he was 34, and he wasn’t exactly an All-Star.

How the deal was received:

With the benefit of hindsight:

Blake was probably better than you remember! The David Freese of his era. Which also overlapped with David Freese. But he wasn’t worth Santana, of course. The Dodgers made it to the NLCS somehow, even though they won just 84 games, but they probably could have done that without Blake.

4. Addison Russell for Jeff Samardzija, Jason Hammel

How the deal looked at the time:

Russell was a top prospect by anyone’s definition, a first-round pick who was the No. 22 prospect in baseball, according to Baseball Prospectus (No. 48 according to Baseball America). He was crushing the Cal League as a 19-year-old shortstop with excellent defense.

If you’re going to trade that kind of player, you’d better get Roy Halladay or Johan Santana back.

The A’s got Jeff Samardzija and Jason Hammel.

Both solid pitchers! Complementary pitchers. When the A’s made the trade, they were 3½ games up in the AL West, and they had just rebuilt 40 percent of their rotation on the fly. That was quite a coup, and Samardzija wasn’t just a rental.

Then the A’s were sucked into a death spiral and spit out of the other side of the Royals’ vortex. They ended up turning Russell into Marcus Semien, which is a fine consolation prize, to be honest.

I’ll wager that Russell ends up with more All-Star appearances, though.

How the deal was received:

Mixed. The A’s fans were excited to get two new starting pitchers, and Samardzija did well for them, but they were understandably wary of giving up Russell.

Cubs fans were thrilled, as they should have been.

With the benefit of hindsight:

If you’re going to trade a prospect like Russell, you should get a star. David Price was traded later that month, and while the Rays might end up getting more than just Russell out of the deal (if Willy Adames pans out, and if Drew Smyly continues to progress, and if ...), they might have preferred Russell at the time.

And yet would Price have been enough to get the A’s past the Royals or Rangers? Dunno. With the benefit of hindsight, just keep the top prospect.

3. Jake Arrieta, Pedro Strop for Steve Clevenger, Scott Feldman

How the deal looked at the time:

No one cared. They aggressively didn’t care. Arrieta was just another one of those Orioles pitchers who flopped after having something of a pedigree, and Feldman was just another arm.

The Orioles were chasing a return to the postseason after their surprising 2012 season, and they were 10 games over .500 and 3½ games back in the AL East. Feldman was having a very Feldman year, which is to say that he was helpful in all the least exciting ways. Arrieta was 26 with 358 bad major league innings to his name.

Plus, it took the smartypantses on the Cubs to reinvent Arrieta. His emergence didn’t happen in a vacuum. Don’t be too hard on the Orioles.

At the same time. My stars, what a coup for a team that was committed to not pursuing pitching in the draft to complement their cache of position players. "We’ll figure out the pitching as we go along," the Cubs said. And they were right.

How the deal was received:

From Camden Chat:

The fact that Arrieta and Strop, combined with what the Orioles press release terms "International Bonus Slots 3 and 4," are worth Feldman, is okay with me.

And from Bleed Cubbie Blue:

At first glance, this looks like an excellent deal for the Cubs. Clevenger wasn't going to be in the team's future plans, and Arrieta -- though he has not been successful in the major leagues -- has been a pretty good pitching prospect for Baltimore for several seasons.

Though some of the commenters were less impressed:

I hope they got a lot of bonus money; otherwise it seems like you could have gotten more for Feldman.

With the benefit of hindsight:

Maybe keep Arrieta and teach him whatever the Cubs taught him, then take the money spent on Ubaldo Jimenez and Yovani Gallardo and throw a huge party? Just one of many possible suggestions.

2. Corey Kluber for Jake Westbrook

How the deal looked at the time:

It was a three-way deal, actually, with Kluber coming from the Padres, Westbrook going from the Indians to the Cardinals, and Ryan Ludwick going to the Padres. The Cardinals were in the middle of a pennant race, of course, and they didn’t have very many prospects to trade for the starting pitching they needed. They ranked 29th out of 30 teams before the season, even, because Baseball America neglected to account for the Cardinals creating their own prospects using the dark arts and forbidden sciences in a bunker under Busch Stadium.

Their solution was to trade a piece off their major league roster, which is always a fun, bold move for a contending team to make. The Padres got involved because they wanted the powerful Ludwick, so they were willing to give up the prospect that convinced the Indians to part with Westbrook. Except it wasn’t a very exciting prospect -- a 23-year-old prospect struggling in Double-A.

How the deal was received:

If I’m being honest, you probably shouldn’t be wasting your time with this article, and you should read Sam Miller on Kluber over at ESPN. He does a deep dive on the weirdness of Kluber in a definitive way, including this nugget:

When the Padres traded him in a three-team trade some three years later, the San Diego Union-Tribune didn't mention Kluber until the seventh paragraph.

It wasn’t a big deal. Not in the slightest. Let’s Go Tribe was fine with the deal:

His other two pitches, a slider and changeup, are less effective due to command issues, so most of the projections I've seen tab him as either a swingman or a straight reliever. If the Indians make him a reliever, he could move fast; if they stick with him as a starter, his path to Cleveland will be more arduous.

The commenters at Gaslamp Ball were absolutely thrilled. There wasn’t a lick of dissent. I’m not sure if it’s a cautionary tale for the next time your team makes a trade and gives up only a C-prospect, or if it’s just an amazing time capsule. Ludwick ended up being awful for the Padres, both in 2010 (when they slipped to second in the NL West race) and in 2011.

And Kluber, well, he was just fine.

This was only the second-worst trade the Padres made that affected this World Series.

With the benefit of hindsight:

Just like with Arrieta and the Orioles, it’s not polite or fair to poke too much fun at the Padres for trading Kluber. If he were a dominant minor leaguer with Cy Young stuff, he would have been untouchable. But he wasn’t, so he wasn’t.

The best feature about Kluber’s rise to ace-dom was written by Albert Chen in 2014.

During his bullpen session, Kluber was alternating between four-seamers that persistently stayed up and two-seamers that he was effectively locating down in the zone. "Let’s stick to the two-seamer," one of the coaches said. Kluber did so, finishing the bullpen by throwing all two-seamers that he located on both sides of the plate, down in the zone, with the precision of a master pointillist.

Is Kluber still in the minors in the alternate universe, struggling to break out because he isn’t throwing his two-seamer enough? Seems far-fetched, except don’t forget that Rich Hill floated around baseball until someone told him to change the shape and variety of his curveballs and focus only on that pitch.

So maybe the Padres were being generous.

JED HOYER: I have to remind myself that some birds aren't meant to be caged. Their feathers are just too bright. And when they fly away, the part of you that knows it was a sin to lock them up does rejoice.

JED HOYER: Also, crap, that guy is on the team facing my new team in the World Series, isn’t he.

1. Anthony Rizzo for Andrew Cashner

How the deal looked at the time:

[loudly coughs]

There was a time, though, when it looked like the deal was fair for both sides. Between 2013 and 2014, Cashner threw 298⅓ innings, with a 2.87 (119 ERA+), and Rizzo hit .233/.323/.419 as a 23-year-old first baseman in 2013.

Still, at the time of the deal, Rizzo was a 21-year-old top-100 prospect and Cashner was a 25-year-old pitcher limited to the bullpen because of shoulder wonkiness. He had the power arm, but he didn’t have the numbers or the clean bill of health. The Padres exchanged their best trade chip (had to make room for Yonder Alonso, after all) for a duffel bag filled with red flags.

The joke still might be on the rest of the league. The Padres turned Alonso into Drew Pomeranz, then turned him into Anderson Espinoza. Then they turned Cashner into some of the Marlins’ best prospects, somehow. This could still work out for them yet.

Just not, you know, right now.

How the deal was received:

I hated it! Did you see that tweet up there? Don’t look up my other opinions. They’re all just as right, please don’t look them up, they’ve all aged fantastically, just like that one.

Gaslamp Ball hated it then, and they probably hate it now. They also do a great Rotten Tomatoes-themed evaluation of trades, and it mostly came up rotten for them.

Bleed Cubbie Blue liked it. It’s really hard to give up a reliever (at the time) for a top first base prospect and have the fans gasp and say, "No! That reliever had closer potential!!!"

With the benefit of hindsight:

Nah, no hindsight needed. The Padres got the rare 100-mph arm, but they were counting on Cashner a) staying healthy and b) making the transition to the rotation. It was a risky proposition for a team that could sure use a little cost certainly every so often.

And yet, it still might work out for them.

The Cubs are happy, anyway.

It takes drafting and scouting and timing and luck to make the World Series. And if you get a chance, it also takes a good, ol’-fashioned heist or five, if the other teams are willing. The Indians and the Cubs have a combined 176 years of championship drought between them. One of them is going to break the drought, and they’re going to use these dumb trades to do it.

A lot has changed since the Cubs last hosted a World Series