The Most Lopsided MLB Trades of the 2000s

There are plenty of big win-loss trades in baseball history. Today we're gonna look at a handful of under-the-radar trades that drastically changed the trajectory of some teams this century.
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00:00 Introduction
01:14 France & Munoz to Seattle
03:22 D.J. LeMahieu for Ian Stewart
05:05 Aramis Ramirez to the Cubs
06:46 Kyle Hendricks for Ryan Dempster
09:00 Asdrubal Cabrera for Eduardo Perez
10:29 Nathan & Liriano for Pierzynski
12:11 Cruz & Lee for Cordero
14:09 Conclusion + Today's Sponsor
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#mlb #cubs #jomboy

[@kevin.skorupa]

I know it hasn't fully played out yet but Ozuna (from the braves) being traded for Sandy Alcantara and Zac gallen along with two prospects is mind-boggling

[@ZachAttack550]

From the braves

[@robertkohl1167]

If Sandy and Gallen retired after last season it still would've been one of the worst ever, especially when you look at what the Cardinals have been running out on the mound since 2021. It just doesn't get the attention it deserves because it was the Cardinals and not the Pirates, Mariners, Mets etc.

[@eazypeazy33]

Now I see why they had to keep him, and let Soler go to Miami. Which I would’ve done the reverse, although they’re the same person pretty much. Until Soler turns it on & thinks it ok to show what he’s really about. That’s one guy who dumbs it down to not stand out..

[@patricknashh]

John Mozeliak should've been fired for this, DFA'ing Adolis Garcia, and the Randy Arozarena deal. the only reason he still has a job is because the Rockies' front office basically gifted him Nolan Arenado.

[@richardtherichard26]

But ozuna on the cardinals gave us one of the greatest defensive highlights of all time. So who’s the REAL winner?

[@Tanner_haines1]

Don’t forget the AJ for Nathan and Francisco trade also gave the twins room to call up Joe Mauer a little later.

[@rjs2527]

Haven’t seen the video yet but as a guardians fan Yandy Diaz for Jake Bauers was CRIMINAL

[@joey5335]

And junior caminero for Tobias meyers 🙃

[@matthewjames6135]

The thing that sucks about it is that yandy would fit in so well with our team right now

[@Papakoolaid16]

@@matthewjames6135 he’d fit well with any team dude rakes

[@bassethound7972]

Jake bauers Yankee legend btw

[@andrewd2652]

Not really, Yandy was never going to be a star in Cleveland because old man Tito would make Yandy ride the bench no matter how well he played. Tito fucking hated Yandy.

[@aqgpandemic5406]

As an O’s fan one trade that I never see anyone talk about is the Erik Bedard deal, traded him to Seattle in exchange for 4 prospects including Adam Jones and Chris Tillman, the reason the O’s of 2012 and 2014 were so good is basically solely due to that trade

[@ericwalsh4881]

lots of people have (okay maybe mariners lol)

[@S_Over_Street]

That trade set the Mariners back 5 years.

[@jaystitzie4743]

As an O’s fan, trading away Arietta and Strop for Hammel probably wasn’t the best move lol. Win some lose some though

[@justinlast2lastharder749]

The problem with that trade wasn't what the Mariner's got. Bedard was lights out, but the Orioles hid some of his medicals. The Felix, Cliff Lee, Erik Bedard rotation was just scary. Jones needed the change of scenery, he was busting in Seattle and losing some top prospect luster. Tillman was unnecessary, Seattle had a lot of Pitching Prospects. It wasn't as bad for Seattle as it seems

[@S_Over_Street]

@@justinlast2lastharder749 the Mariners had many OFs when Adam Jones was a top prospect in ‘06-‘07. It was Management that screwed up not fully committing him playing time. The Bedard trade was awful for the Mariners. He had an attitude problem that irked not only the local media but the fanbase. Plus he never wanted to pitch past the 5th inning.

[@johnnymoondog9474]

In the AJ Pierzynski trade the Twins also acquired the awesomely named Boof Bonser. Watched him pitch in AAA. I believe he was inducted into the Hall of Occasionally Pretty Good.

[@danielfranklin9271]

He was one of my favorites when I was a kid just bc of his name

[@friggy1899]

Rick Wise one-for-one for Steve Carlton is one of the most forgotten one-sided trades. Cards got 7.7 bWAR in Rick Wise, while the Phillies got 64.6 bWAR in Hall of Famer, 4x Cy Young winner, Steve Carlton.

[@derekp3820]

Really appreciate you going through different names as opposed to the typical deals everyone knows about

[@adamd5849]

I love that the Cubs were featured in three entries on this list, and that didn't include the Arrieta deal

[@nashCDN]

These trade videos have been some of my favourite videos from you, keep up the great work man!

[@Fly-The-W]

Really hope Hendricks can get back to somewhat his old self when he returns. Love watching him pitch. Doesn't blow guys away with power but when he's got his stuff working its a thing of beauty

[@qatar824]

That 2016 Cubs team was loaded with candidates for this list. Also, as a Twins fan, we weren't particularly upset about losing Pierzynski, because his days were clearly numbered with Minnesota's Baby Jesus (Joe Mauer) on the way up.

[@SpiritStoneWarrior94-yx3gs]

Joe Mauer was one of my favourite catchers of all time tbh! I used to always trade for him back when i played the baseball game on Wii called The Bigs. Also just loved following him in real life, too, and as a Giants fan, he's only just behind Posey for my favourite catchers since i started following baseball in 04

[@aquila519]

​@@SpiritStoneWarrior94-yx3gsMauer and Posey were the 2 best catchers in the league at that point. They were so good

[@perryno99]

Erik Bedard for Adam Jones, Kam Mickolio, Chris Tillman, George Sherrill, and Tony Butler

[@FlyingDwarfman]

#3 in Zduriencik's "Big 3" franchise-crippling trades. #1 was the Perez-for-AsCab trade the video mentioned. #2 was the Broussard-for-Choo trade just a few weeks later. The guy literally gave up 4 already-then-known-would-become-All-Stars plus extra for... a DH platoon pair and SP who'd break in his first season. He gutted the team's OF and MIF depth for... negative net WAR. It was so bad that I recall an All-Star Game broadcast some years later and their "fun" stat was "count of All Stars by team farm system". The Mariners' system led the league... and not a single one of those Mariners-developed All Stars were playing for the Mariners. And it still took another year for Zduriencik to get canned.

[@benjaminlincoln3025]

I've always thought the Mark Teixeira to ATL was lopsided towards The Rangers considering it set up their back to back world series appearances.

[@TheTEN24]

Appreciate you covering some trades that other channels haven’t before and not the big ones always talked about. Great content as always jolly

[@matthewaltepeter8941]

5:05 I brought this trade up in the comments of the video that you mentions at the start of the video. The cutoff for that video was 29 WAR differential, and I without even looking at the totals, I knew that had to be very close to being the cutoff point.

[@nacoran]

Going back farther, a couple Houston trades involving 1st basemen... one coming in for a steal, and one going out (great player, but promptly injured.) Bagwell became the face of the Astros for his career. Before that, when Houston traded Glenn Davis for Schilling, Harnisch, and Finley.

[@swilliams21231]

I loved Aaramis Ramirez and Derek Lee at the corners. Those were some fun guys to watch. The cubs have had some wildly lopsided trades in recent history, Hendricks, Arrieta and Strope, Rizzo

[@adamdavis2760]

Seattle traded Jason Varitek and Derek Lowe to Boston for Heathcliff Slocumb. We are talking about a guy with a 5.79 ERA and allowed 95 baserunners in 46 ⅔ innings and a WAR of 0.4 in his 2 years In Seattle. The Sox on the other hand got a franchise catcher/captain for the next 15 years as well as a pitcher who was an all-star for Boston as a closer and starter.They both were a big part of 2 world series teams as well as having a combined 43.6 WAR during their time with the Sox. I will say though a couple years before that Seattle got Boston good when they traded Darren Bragg to the Sox for some guy named Jamie Moyer...that one hurt a bit

[@joetoscano6376]

Jolly does not miss, every video is so well done, big love Jack! if you’re going to still do another trade video, maybe shortest trades? like when Piazza was flipped from LA to Florida then to the Mets.

[@CMG_Sports_Podcast]

I love this series! Trades and Free agency are my favourite part of baseball and this series let's me learn

[@TheArmstreet]

I did not know a lot of these. Thanks man. You are one of if not my favorite baseball creator on youtube.

[@Hooper1254]

Legit was talking about the Pierzynski trade with the homies this week! Ur the man Jolly

[@Mystery-br2mu]

I would love to see 3+ team trades. See how it all balances out.

[@MK1trey]

I love getting an Asdrubal Cabrera highlight. Great video as always!

[@JQ-vn5ky]

Love the aramis ramirez love

[@matthewaltepeter8941]

11:22 Boof Bonser is probably he best baseball name I've ever seen

[@greendayprn792]

Great video! Enjoyed all the way through

[@joshuawilmoth1452]

Just noticed u have hit 700k subs. Congratulations Mike!🎉🎉🎉🎉 keep up the great work and content.

[@owenmadigan-fried6167]

thank you for including the clip of dempster hitting arod. i’ll never forget that

[@bsovvy07]

As a tigers fan, literally Verlander, JD Martinez, castellanos, Upton, and more

[@Korijenkins1414]

The Verlander trade is easily the most underrated of the last decade, and probably the most lopsided as well. 61-19, with a WHIP under 1 every year he pitched, an ERA of like 2.3, and obviously loads of postseason success. He may not have been great in the World Series, but he was instrumental in getting there as many times as they did. And to cap it off, his final game as an Astro was a win in game 5 of the World Series to take a 3-2 series lead. And the Tigers got... nothing. I question the sanity of the GM who approved that deal.

[@katieg2449]

Another trade video idea could be in division trades, especially preseason they can be headscratchers

[@sbarajasjr]

One of the most lopsided trades was Adrian Gonzalez, Chris Young, and Termell Sledge to SD from TX for Aki Otsuka and Adam Eaton

[@paulschild8924]

Idea: The greatest player to be named laters of all time

[@adamfurphy4054]

Matt Brash was a PTBNL in the France/Nola trade

[@PNW30568]

The Mariners trading for two key pieces, Andres and France, and we gave them Nola. Thanks San Diego

[@asdfaeou]

Jolly, you're so good at structuring videos. The list of "here's what we're doing, here's what we're not doing" is so good. Watching you succeed is wonderfully fun.

[@IntriguingGamers]

this video was great, keep up the great work

[@tylerssportscardsandmore8345]

perhaps a videos about teams trading with their rivals. seeing notable trades with the sox and yanks and dodgers and giants and so on

[@ryanmccarthy7381]

Great video, Jolly Olive.

[@PpP-dr1od]

Fielder, Braun, and Cruz would be scary. They'd combine for 250 RBIs and -150 DRS

[@robertkohl1167]

The best/worst/funniest part of the Asdrubal trade is that he was only the 2nd best player the Mariners traded away for a bad Cleveland 1B that season...they gave up Shin Soo Choo for Broussard less than a month later. Shame the non-waiver deadline wasn't a month later...Cleveland probably could've gotten King Felix for Ryan Garko.

[@josesilvestre2204]

Aramis Ramírez is very underrated

[@lennartrhee3730]

How about the franchise altering, Arrieta and Strop trade with the Orioles. Without this trade, the Cubs wouldn't have won it in 2016

[@ygf377]

Yes but everyone knows it even thought the hendriks deal was much better as hendricks was more valuable than arietta in each year they played together exept 2015 and he is still with the team

[@Xero328]

Could u cover the Mets trades following 1986 thru the 90s? One that never gets talked about is McReynolds and others to the royals for saberhagen and others.

[@ryans1327]

damn you jolly... as a bucs fan i have certainly not "forgot about" the ramirez/lofton dump. guess not all your viewers are of the mainstream elite mlb ilk, goddamn you. THE JOLLY ROGER SHALL RISE AGAIN

[@theanimedad7318]

Funny you mentioned Carlos Lee. Lee was dealt from The White Sox to the Brewers for Reliever Louis Visciano and speedy outfielder Scott Podsednik. Podsednik's metrics aren't great by todays standards (He had 0 HR's in 2005) but this was the exact kind of player Chicago manager Ozzie Guillen wanted in his lineup. Podsednik definitely lacked power but he was a great table setter for that '05 Chicago team getting on base w/ a .351 avg and stealing 59 bags. He helped propel them to a world title that year.

[@neiltooreal]

Great content as always my friend

[@shaylarz]

As a part time Rangers fan I am grateful for the Cruz trade to Texas. That’s where he became one of my all time favorites and remains so to this day.

[@bryantsteury8910]

Ramirez to the Cubs was so epic for the first few years. Loved his time here

[@crowtservo]

6:14 The Pirates had overestimated the revenue that their new ballpark would bring in. They ordered the GM to cut payroll by any means necessary by owner Kevin McClatchy. So Ramirez and Brian Giles were both traded away for cheaper players. They also rushed him to the majors in 1998 and didn’t get a good season from him until 2001.

[@jcarwash31]

Boof was worth -0.2 WAR in his 3 years with the Twins. I think he stuck around that long because people like to say Boof.

[@danthepug7374]

The cubs also made 2 more stellar trades around that time, getting Pedro strop and Jake Arrieta from the Orioles for almost nothing, and then Anthony Rizzo from the Padres for Andrew Cashner

[@user-er8le9hn6v]

Crazy to ignore the fact that the Twins also got Boof Bonser, the best named player in baseball.

[@zesolodar]

im going to throw in a few trades here that hardly ever get mentioned is when texeira got traded to the braves. the rangers gave up a player who most likely wasnt going to sign and in return got matt harrison who turned out to be a solid back of the rotation guy for years, elvis andrus who was a good player for years, and feliz who was one of if not the best closers in the league for a while and i think we have had a much better longer career if the rangers didnt try screwing around making him a starter. then braves trading justing upton and northcraft for max friend e and the tarde the braves made for tim hudson

[@bassethound7972]

Really interesting video bro

[@mukkslide27]

the fallout plays outro music playing is throwing me through a MASSIVE loop

[@poodlecrap1237]

Fun fact about one of the other guys in the Nelson Cruz trade. Kevin Mench was my neighbor as a kid after he retired, and he wore the largest hat size in baseball at the time (8 1/4), and was nicknamed Shrek.

[@OilCompany95]

Aramis Ramirez is extremely underrated.. I figured you'd notice jolly lol, was waiting for him on ref guess lol

[@Miguel-jb2ww]

Is there another video that mentions the Fred McGriff trades??

[@HeyCupertino]

Tom Emanski's Baseball World Defensive Drill Video.

[@brandongell35]

Babe wake up, Jolly Olive just posted

[@ByiLHS]

I thought of Shin-Soo Choo for Ben Broussard, the A's three team trade for Johnny Damon and Mark Ellis, Ramon Laureano for Brandon Bailey, Josh Hamilton for Edinson Volquez, and the Seattle Erik Bedard trades

[@Extinguisher10]

I hate to check the date of this video when you said Andrés Muñoz is a setup man. It's okay, I forgive you. Most New Yorkers forget the Mariners exist so you're ahead of the curve 🤪

[@Extinguisher10]

I'm looking at you @giraffeneckmarc

[@TheBarrier]

Marco Scutaro to the Giants? Crucial to their World Series win in 2012, happened during the same time the Dodgers pulled off their blockbuster

[@beastModeRocco]

Jolly hating on my man Boof Bonser dang

[@adamknudsen.41]

Love this video (I am a cubs fan)

[@mattcollett9370]

Before I watch, I hope AT LEAST one of Bautista/Encarnacion to the jays is included in this vid

[@ryangilbert8527]

Crazy how much the cubs have given up. They drafted josh Donaldson, gone. Traded away eloy Jimenez and Dylan cease. Crazy

[@ygf377]

Yes but they have made great deals as well such as the arieta deal, the henricks deal and eaven in recent trades they seam to have fleased the yankes geting a very promising starter in hayden wesneski for scot efross whoe went down with tommy jhon and the baez trade is looking like it may age very well

[@danr154]

Ahhh yes I definitely remember Aramis Ramirez. Great hitter. Good defender when he could get to it. A bit slowed by injuries. Terrific RBI man. Miss him greatly, the current Cubs could use him badly. Hes was the definition of the Hall of Very Good😂

[@Evan-xp9uh]

As a Phillies fan not a day goes by when I don’t think about the hunter pence trade and how we got shafted with the prospects

[@mloftus8618]

I’d also say, that the Orioles trading Jorge Lopez to MIN for several players last year at the deadline was a killer/underrated deal. Jorge was a great closer and has been good for MIN, but BAL got back a handful of guys including prospect Cade Povich, and….Yennier Cano! At the time, not very impressive names in return. But Povich has really started blossoming since he came here, and has upped his velocity and control and is on track to join the SP rotation here in the next 2 years. And Cano?…well, I think we all know just how dominant he suddenly became since being called up to start the season. He is arguably…and certainly by the numbers…the best reliever in baseball right now. I was sad to see Lopez go, but this trade has been unbelievably good for BAL so far.

[@shoukatsukai]

Way too early, hasnt even been a year yet.

[@mloftus8618]

@@shoukatsukai - it’s been a year, fyi. And as someone who has played, and coached, baseball at a high level, it’s easy to see the generational talent. Which part of his game are you concerned about? If you don’t think this player should be protected and extended, I’m curious to know what I’m not seeing.

[@EtaM29]

If you look at the twins trade they traded away Liriano which got the Eduardo Escobar who on his own was a pretty good infielder then he was traded and in the trade twins got current star closer Johan Duran

[@bo0chie9]

Was really hoping for Bartolo for Grady Sizemore, Cliff Lee, and Brandon Philips!

[@Knabtube626]

I’d put the Eric Bedard trade on this list. Yeah even though the best returning player was Orioles franchise player Adam Jones, it’s the fact that Seattle just tossed him aside in favor of Willie Bloomquist. It’s a shame that Bedard was a bust in Seattle because he was a BEAST in Baltimore.

[@TheAlchemistL]

Jolly upload every Saturday noon hits like crack

[@romanrodriguez4330]

Yandy Diaz trade to the Rays should have a mention. Randy Arozarena from the Cards… Drew Smyle to the Mariners for Mallex Smith and Ryan Yarbrough….

[@Hogtownboy1]

Please do a video on most tanking trades. Those made to intentional made to worsen a team.

[@broadstreetbullies849]

Dempster ended up winning the World Series with the Red Sox in 2013 which I find hilarious

[@danwestern7862]

The number of Brewers strikeouts shown in this video was painful, then the last trade was the cherry on top 😢

[@a1gamer561]

Can’t wait to see the Luzardo to Miami trade in one of these days the next year or so

[@Leaderofmen69]

As a padre fan, you could’ve dunked on us in this entire video, Kluber for Ludwick, Cashner for Rizzo, etc etc

[@StewBNick]

Dan Straily to the Marlins for Luis Castillo back to the reds. One of the biggest finesses of recent history. And one of the very few trades the reds ever won

[@seanknapp1]

as an 18 year old i don't remember aramis ramirez as a cub but when you flipped to his baseball reference and some pirates pictures it click. For some reason he is a pirate in my mind.

[@hitmangfx7162]

I remember Aramis Ramirez. The guy felt like a steal and he just...kept hitting. For, like, a long time. For some reason, I have him mentally linked with Adrian Beltre.

[@randymartin1727]

Good list Mr. Olive, but what about when the Angels traded a Monkey's Paw wish for Tungsten Arm O'Doyle

[@2dmc_brian]

What’s the comparison between the Perez-Cabrera trade v the Broussard-Choo trade? I think the WAR split is close

[@skloiber101]

The Royals trading Greinke in 2010 was a crazy win for the Royals

[@cjisawesome3686]

The Cardinals trade of Colby Rasmus was One of their best trades. A solid player for three Stud pitchers, and a solid outfielder 🤓.

[@EonArashi]

Thought for sure the Mariners miss with Cleveland was going to be Ben Broussard for Shin-Soo Choo. -0.7 bWAR to 21.8 bWAR.

[@nicofaraguna8972]

Regardless of the three SF championships, in the 2010s... this trade still haunts me

[@Ekohtwo]

The marcel ozuna for zac gallen and sandy alcantara trade is also noteworthy

[@jbj7599]

Wasnt Cruz DFA before he broke out with Texas? I know he was, just cant remember when

[@AndrewCordescordsfam]

That Braun, Cruz, Fielder 3,4,5 would’ve been crazy

[@broadstreetbullies849]

I definitely think Glen Perkins was better than Joe Nathan but your point still stands

[@nickpiccolo9106]

Nelson Cruz is one of the greatest "What ifs" in Brewers history

[@Shortyd17]

The Reds getting Luis Castillo for Dan Straily and Eugenio Suarez for the corpse of Alfredo Simon are two elite trades as well. They might’ve done it again with Steer and CES for Mahle.

[@rvaneand326]

6:34 “dangit, Bobby!”

[@gaben_watch]

Deal hasn't fully played out yet, but the Dbacks gave the Cardinals Paul Goldschmidt in exchange for... Luke Weaver Carson Kelly Andrew Young Competitive Balance Round B Pick in 2019 Draft (became Dominic Fletcher) Ouch.

[@GEREIKAT]

Giants fans never forgot about the Nathan-Pierzynski trade. We were mad the day it happened and we're still mad about it to this day.

[@Itswebbgaming]

WOW didnt even utter the mans name, the legend Boof Bonser.

[@caseyhayward8094]

to this day, still no one acknowledges the Erik Bedard trade in 2008. Orioles sent Erik Bedard to the Mariners for a package that included Adam Jones and Chris Tillman. Jones and Tillman were franchise cornerstones for the Orioles 2010s playoff squads while Bedard never stayed healthy and left Seattle after a few years. i never see it ever mentioned in any videos of this sort.

[@FireEmblem2413]

Love Rami, glad to keep Pittsburgh in the spotlight for bad trades. I still think that the Carlos Gomez deal was one of the worst trades in the last decade, never seems to get as much love.