The Most Lopsided Deadline Deals in Recent MLB History

With the pressure of the Trade Deadline clock ticking away, sometimes baseball GMs make some poor judgement calls. Here are some of the worst.
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Sources:
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#mlb #rangers #royals

[@JollyOlive]

09:34 For those wondering why Buster Posey wasn't included here, this statistic had a set value of 80% games played at catcher. When lowered to 50%, it also includes 2012 and 2014 Buster Posey, accounting for his time played at first base.

[@austinjohnson9059]

My goat Buster Posey

[@Texpantego]

I'm not sure Texas wins the World Series without Chapman. His outings were stressful, but he did generally get the job done.

[@residentlando]

especially in most of the playoffs

[@Acquirebread]

It was a reasonable trade imo. Ragans was not pitching well in minor so giving him up for high leverage reliever for playoff makes sense

[@davidbondy2250]

Chapman's presence improving the bullpen is enough for me to consider the trade a success. I honestly don't care if Ragans becomes a hall of fame pitcher, Chapman's presence helped the Rangers win it all.

[@titoslounge1946]

Cubs don’t win the WS without Chapman. He pitched 2.2 scoreless innings in game 5. We only had him for a half year and gave up an arm and a leg for him. Still worth it.

[@dre32pitt]

"His outings were stressful, but he did generally get the job done." That can go on his tombstone as that's been the case since he came up lol

[@SurgingSpecs]

That Marquis commercial is genuinely one of the funniest videos on the internet

[@jasonwilliams4621]

You know it's a great Saturday when jolly posts

[@JacksonMars.]

As a Rangers fans, I am grateful for the Chapman/Ragans trade. It would obviously be great to have Ragans back this year, but with baseball, you just never know if things would've turned out the same way, so I'm glad the trade went down, and I'm glad to see Cole doing so well in KC!

[@mostly_baseball]

ngl the Juan soto trade was pretty lopsided in Washington's favor, SD got 1.5 years of soto and Washington got many top porspects, with james wood and McKinzie Gore leading the pack

[@SmoothCriminal12]

Would've worked out way better had Aj Preller not fucked up the payroll with the Bogaerts contract/Darvish extension and had the money to keep Soto. But alas, Preller is a clown.

[@mgasolprodz33]

Yeah, the Padres got back Michael King for James Wood, CJ Abrams, and MacKenzie Gore if you really think about it

[@lincolnmckay555]

​@@mgasolprodz33Also, Higgy and Dylan Cease.​

[@PatDK]

@@SmoothCriminal12Soto was never going to stay though bro… no reason to get mad at somebody for trying to get a bit back for him… I don’t think he’s going to sign with NYY before the start of free agency, so it’s smart to get something for him after he tries to go all out and the team shits the bed

[@ghostofmoredishesmorebitch1507]

@@SmoothCriminal12yes bc preller could've predicted their owner dying and bally not being able to make payroll years ahead of time😂

[@WyattBoatright]

Love the Pokemon music in the background

[@Bubby0304]

Thats what im saying, more fitting than you would think

[@adriansym]

I would argue Ragans is a win win because Texas won a world series (If not than it is at least not a loss for Texas)

[@NDTexan]

I mean sure, but they didn't win it because of Chapman and there's an argument they would have won it without him pretty handily. I'm not saying do it all over again but having Cole Ragans in his prime and still under team control for a few years is a big oof

[@CMed14]

@@NDTexanMemes aside, Chapman came up big in the Astros series, which was the pivotal one.

[@beardybrowsingdude]

The amount of hand wringing when Chapman couldn't get his location down took a few years off of this Rangers Fan's life last season.

[@mvp_pr1255]

@@NDTexanyeah but how could they know that he would be like this, he was horrible in Texas and you needed a better lefty yeah Chapman was good sometimes but still its a win win, gotta give praise to the Pitching coach in KC for unlocking something in Cole Ragans that became who he is

[@rp3569]

No, just no

[@bologna_lover]

as a royals fan, having cole ragans and seth lugo leading our rotation honestly feels like a dream. we've been so bad for so long, that having 2 dominant starters that when they're on the mound, we expect to win and have optimism surrounding them feels so foreign to me

[@ryanmooney6051]

Brady Singer isn’t too bad either.

[@tyrrellhueston8588]

Dominant ? 🤣

[@austin23h46]

@@tyrrellhueston8588yes dominant is what he said and it’s very well true

[@griffinhays2053]

I would blame the Ragans thing on Texas failing to develop him more than the trade. His velocity jumped even further in KC which can't be ignored, and has been arguably the biggest piece of his breakout

[@chipper7244]

That’s the rangers way, can’t develop pitchers, hopefully their next batch of minor league pitchers can develop

[@gcubed5451]

The one and only time the Royals have successfully developed a pitcher

[@Carlos-uf8so]

Sure the velo jumped but he has also already had two TJ's I believe. If he blows it again his career might be done.

[@joshdelagarza231]

As a Rangers fan this is the correct answer. The Rangers have NEVER been good at developing pitchers. Ragans needed the change of scenery.

[@CoreyPoindexter]

I think it's tough to judge a trade for a player like Ragans. Because, yes, he's doing much better in KC, but it's entirely possible that his performance is due to change in pitching coaches and staff. Sometimes guys say they go to a new staff and the mentorship just clicks something in them. It's entirely possible Ragans stays unproductive in Texas because it's not a right fit for him, so in that sense, he would've never had the WAR value in Texas. Idk, just my 2 cents. I'm a Braves fan, and I remember Mazzone helping shape a lot of guys who might not have had the same career elsewhere.

[@lanastan322]

Trading Ragans for your first ever World Series ring seems not lopsided

[@skrubgod]

I personally kinda want to see a lose lose or pointless deadline deals videos tbh

[@TVBenSifka]

Texas literally doesn’t make the playoffs last year without Chapman. He unironically is the reason we could even get to the World Series in the first place. I also highly doubt that ragans is even close to his current self with the rangers pitching dev. It’s just historically awful

[@XenonSwift]

Win-Win for the Royals/Rangers swap. Rangers reached the WS and KC got a starter for the future. Ragans could not figure it out with the Rangers and the change of scenery and the tweaks to his mechanics is probably why he's been dominant in KC.

[@somerandomguy5977]

Koji Uehara striking out 12 K/9 with an upper 80's fastball not that long ago proves movement can be as effective as velocity if not more. Even analytics nerds go between velocity and movement. Although they always ignore command.

[@ianb8250]

Great video as always, Jolly! Really enjoy all the content you and the JM guys make

[@joetoscano6376]

kept cardio going so I could give this my full attention. damn you, Jack. tricked me in to an extra mile and change

[@CharlesTC]

I’ve always thought people don’t talk about how lopsided the Matt Holliday to the Cardinals trade was

[@SmoothCriminal12]

And that was AFTER dealing Huston Street and Carlos Gonzalez to get him for a delusional playoff push.

[@BigPat216]

I love this channel so much, and seeing these names I grew up on. And the random commercials you find like that Marquis one, I have no idea how you can find that.

[@somerandomguy5977]

The Rangers won a ring so any rental is worth it according to most. Players would rather have rings than regular season wins I can tell you that.

[@noylakers9755]

There are a lot of hindsight in these kinds of videos, but I do find it very interesting. I'm also on the side that I'm perfectly fine with giving up prospect to win a championship. I think it also has to be stated that some of the players mentioned wouldn't have developed the same without the change of staff/scenery. Lets face it, some teams are horrible at developing players so they are better off trading for established players because a lot of these high skilled prospects won't become stars under their hands.

[@kami_in_the_skye]

Love it when *the* Joyful Jackfruit talks trades.

[@charliep123]

For Blue Jays fans, Ragans will always be “the guy who fell over on the mound” (if you don’t know what this is about, Jomboy did a breakdown on it)

[@shinypokes2288]

Idk if you've mentioned it in a previous video but the Angles trading away Raisel Iglesias to the Braves for Jesse Chavez & Tucker Davidson has gotta be one of the most lopsided trades I've ever seen. Chavez was absolutely miserable for the Angels and got DFA'd and went back to the Braves later that same year, and Davidson had an ERA of over 6 with the Angels before getting traded to the Royals in 2023. Meanwhile Raisel has been a consistent closer for the Braves and has been rocking a low 2 ERA for them since the trade.

[@kamakazi9255]

Always look forward to these videos. Great work as always

[@georgecarson6631]

Aroldis Chapman was a heart attack every time he pitched, but but he was an extremely important piece of our bullpen in the postseason. With hindsight, a big postseason contributor that helps you get a ring is worth any price. Cole Ragans could win several Cy Youngs and multiple rings in the future and I still would not regret the Rangers trading him for Aroldis Chapman.

[@taylorpowell8728]

Not sure if it's been covered before on your channel, but the 1997 trade of Heathcliff Slocumb from the Red Sox to the Mariners in exchange for Derek Lowe and Jason Varitek worked out pretty nicely for the Red Sox!

[@KneeDeep2231]

A bit unrelated but I appreciate the consistent use of Pokemon DP era music as someone who loves Pokémon Platinum

[@JabroniBaseball]

The Robbie Ray deal still keeps me up at night

[@blakeattig5426]

I don’t really agree with the Ragans/Chapman trade on here. Like sure, it’s lopsided when looking at the trade by itself, but Chapman was a contributor for a World Series winning team as a rental.

[@xypherus777]

As a Padres fan you could include 2 of their trades from 2020 on this list. The Clevinger & Nola trades were huge losses for us. Cleveland getting a key piece to their hitting core in Naylor and Seattle getting one of their best bullpen arms in Muñoz AND a pretty solid bat in their lineup in France all for the Padres to get a pitcher who pitched 4 games before needing TJ surgery and effectively being cooked and a catcher who's hitting regressed to being worse than the average pitcher.

[@Pittsburgh0Yinzerkid]

If you do another one you should include the Chris archer trade with the pirates but other then that this was a great vid

[@patrickdare5356]

Doyle Alexander (6.4 WAR from 1987-89 with Detroit, plus leading them to the 87 AL East title before they lost to eventual WS champion Twins in playoffs) vs John Smoltz (66.9 WAR from 1988-2008 with Atlanta, plus a HOF election in 2015).

[@thatgingermatt]

BABE WAKE UP. NEW MERRY MANGO VIDEO DROPPED

[@TheMostCasualLurker]

@@thatgingermatt lame ass

[@ButterflyBlood]

Ramos' injury right before the playoffs in 2016 is the most consequential injury in Nationals history outside of Stras succumbing to thoracic outlet.

[@stephenellsworth964]

Jolly, love the content, and a big fan of Jomboy Media. If you haven't done this video yet, how about your Top 3 favourite MLB trades of all time? Or even Top 3 favourite waiver claims?

[@aaronlarussa6180]

Pokémon music as the background music is just perfect

[@Bdnelson89]

Jolly, if you think the Marquis ad is wild. Go find the other Nationals ads from that year. Including one for Wil Nieves

[@BenXParsons]

Oh the Ragans trade will get more ugly that’s for sure but in the end of the day I don’t think the Rangers care cus Chapman is one of the key pieces of them even winning the World Series and without him they wouldn’t have won it so I would have still made the trade personally.

[@davidcherman1]

Slight correction - Ragans' 2nd TJS was correcting a mistake in the first one so it wasn't a separate procedure. This is an important distinction because his ligament didn't retear a 2nd time

[@Jack-h8n8z]

Love the vids Jolly!!!! I love the type of videos you make!!!!

[@thegoodtony3339]

Love the video, channel, and content. Another gem. Thanx

[@chrisofchris]

Flags Fly Forever. I’d do the Chapman/Ragans deal 10/10 times

[@emilyg3758]

Love the main channel content as always Jolly! LFGM!

[@corbinm5237]

The first Chapman trade was one people also said would age poorly for the acquiring team,but it turns out it aged really well. Given that this is only the first full season for Ragans in KC,it’s way too early to say if this trade was a regrettable one for the Rangers,even despite winning a World Series.

[@samgc3650]

Sorry Olive, but I think if the trade gives you the ultimate goal, it will always be worth it. I will trade an entire roster of prospects full of hall of famers if it guarantees a World Series. Ragans can go on and win for the Royals multiple championships, but in the end Rangers got what they wanted

[@williamdeguenther161]

The Braves made a number of them in 2021, but the best, to me, is Jorge Soler. The Braves gave up Kasey Kalich, who is still in AA, and got Soler. Soler accumulated 1.1 WAR in Atlanta, had a 131 OPS+ and claimed WS MVP.

[@christmashake8968]

One lopsided deal that doesn’t get talked about enough, imo: the 1987 swap the Tigers made for Doyle Alexander, giving up one John Smoltz to Atlanta in the process.

[@freyplays1099]

Always love the Pokémon music in the background 🥰

[@darkchocolate3390]

Didn't think I'd get a baseball video filled with Pokemon Gen 4 music, but here we are.

[@justingerald]

When you flash the "6 50 hr seasons" and 2 are Judge (with a strong chance he does it again this year), I am happy.

[@TheLickalittle]

I was at a game where Matt Capps blew a save against the brewers. Only time I’ve seen twins fans boo a home player.

[@ABoeing-]

Been waiting for the Ragans talk. Devious thumbnail 😈

[@reedl.wilton312]

Hello Jolly. You are very good at making videos. That is all. Have a nice day.

[@PpP-dr1od]

I was waiting for the Ragans trade to make a list, but honestly reliever trades are goldmines for lopsided trades WAR-wise. As a Phillies fan, the 2022 Ben Brown for David Robertson trade might 'haunt' us, and I wish we still had Brown, but the team needed bullpen help and that run to the WS might not have happened without Robertson. Even the 3 bullpen trades in 2020, all trades for players that were awful in a season that is dead to me, are trades I will still defend. The team wasn't good enough to invest much, but too good for a team with such a bad bullpen to not try to fix that issue in an expanded playoffs year. The team gave up very little for David Hale and David Phelps, and while they gave up Nick Pivetta to get Brandon Workman and Heath Hembree, I was more upset that they had given up an ok prospect, Connor Seabold, since Pivetta had made it clear he had the talent, but it just wasn't going to work in Philly.

[@jalenking810]

Bro has MLB power pros and Pokémon platinum music all in his videos. We really had the same childhood

[@generallukeproductions]

As a Rangers fan, Ragans never would’ve become the Ragans we know now had he stayed in our system. We can’t develop pitching.

[@RileyJane7]

Every time the gen 4 music plays, my smile gets a little bigger

[@DJDan07]

On July 2, 2013, the Orioles traded Arrieta and fellow pitcher Pedro Strop to the Chicago Cubs in exchange for starting pitcher Scott Feldman and catcher Steve Clevenger. One of the worst trades ever. Arietta goes on to win a CY young award and a WS breaking an all time curse with the cubs. Lopsided? Absolutely.

[@rellimnahtan]

Rangers fan here... I don't like Chapman as a person and I think his role was one of chaos more than usefulness, but I'm totally fine with the trade because 1- world series win, and 2- the rangers are not a pitching development team, and may never be. Here in Texas we do big offense to the point where defense doesn't matter. Texas' pitchers give up 10 runs per game? Totally fine, as long as the batters score 11. It is the Texas way.

[@michaelsomsen22]

As a Giants fan this still hurts to this day. Zack Wheeler for Carlos Beltran

[@Sicknilva4]

It definitely stings a little bit seeing Ragans pitch so well for the Royals, but at the end of the day, the main goal in baseball is to win the World Series, not to accumulate good young players. The Rangers did the former, and Chapman did help, so nothing else really matters. If they lost tho this would probably go down as one of the worst trades in franchise history. I guess we’ll never know😊

[@arlo9091]

Chapman was one of only three relievers Texas used in the playoffs, anyone actually watching their world series run knows he was key to keeping the bullpen running, that's wasn't a loss by any means, led to a championship, and Ragans just wasn't working out in Texas.

[@peterskrobola8753]

Jolly make a video on the all time meh for meh trades. Gregory Soto and Kody Clemens for Matt Vierling, Nick Maton, and Donny Sands is definitely on track for that.

[@dusatriplife333]

Love the Pokémon ost’s😭🔥🔥🔥

[@zackkorth2410]

ragans for chapman is a great trade for both teams, tex won a world series and kc got an ace. doubtful that the royals will be winning a world series anytime soon, so you could say it was a win overall for texas, crazy as that seems. impossible to know what he becomes if he stays in texas, maybe he hates the heat? he probably still would have been an ace there but they won it all for the first time ever.. so i think that's a really good trade.

[@BubbleBAss-fi8jl]

The Twins 2022 deadline could be mentioned in the next video. Minnesota got 1 season of Jorge Lopez with a near 5 ERA and not even 10 starts of Tyler Mahle for Spencer Steer, Christian Encarnacion-Strand, Yennier Cano and Cade Povich

[@BigPat216]

That was a weird and ugly trade.

[@Speedster___]

Povich GBR

[@ferdinandfoch7816]

The Mahle trade was at least defensible at the time because young starting pitchers are so valuable, and Mahle had a pretty good track record before the trade. But then he got bit by the injury bug. The Jorge Lopez trade was terrible at the time because Cano nearly major league ready and we traded him for a relief pitcher with less than 70 innings of good pitching in his whole career, not to mention the inclusion of other prospects on top. Just an awful trade from soup to nuts.

[@andrewbloom7694]

2:22 Id love to know that dudes reasoning. Ray lead the league in: Sabermetric stat ERA+ Traditional stats ERA, WHIP, SO And GS and IP which the traditionalists would value more. I dont really know what stat combo would have convinced him...

[@eshep71]

No one will believe this, but I do have screenshots.. and yes, I used them to piss off my friends all summer lol Pre 2021, my friend and I were discussing CY candidates/predictions and I gave a spiel about how Robbie Ray would win in the AL. (Basically cut walks from 6/per9 to under 2) Not as pure, but also impressively, I picked Corbin Burnes as well, but as a dark horse. (I had no AL dark horse) My primary was Dinelson Lamet (lol) who didn't make it out of spring. In my head, I sometimes wonder how much Ray's CY young odds were that year., tho I don't gamble. I've never felt so proud and worthless at the same time lol

[@cuddyfox6973]

I think Texas made a mistake in trading Roby and Saggesse to the Cardinals for Montgomery. I know they won a ring, but Saggesse is letting the ball fly in AAA and on top of that, they got John King too, which is making himself a home in the majors bullpen for the Cardinals.

[@thanhtuan8609]

the Rangers got a bunch of Saggesses in their farm, they did not have a single Gumby, who btw, was one of the main reason they got to the postseason and won the whole thing. Not sure how you could call that a mistake

[@BrandonKClark86]

Not sure on the numbers but would lover for you to look at the jeff kent for matt williams trade in 97

[@Mundo.562]

I love trade videos. Please do more 🙏

[@TryPuttingItInRice]

judging the trades simply based off of the war provided in their time with the team is flawed and it shows with the Chapman for Ragans trade. Ragans has been pretty good for the Royals, but they haven't won anything and neither has he for that matter. meanwhile, Chapman was a key piece on the championship team. for the 2nd time in his career at that lol.

[@ferdinandfoch7816]

The Twins should be on here again for the CES+Steer+Hajjar for 42 innings of Tyler Mahle trade. Also deserve a dishonorable mention for Yennier Cano+Cade Povich for 58 innings of a below replacement level Jorge Lopez.

[@ericchilders9234]

You win your first world series anything was worth it for the Rangers

[@DaveGentry-ik6qq]

Not a deadline deal, but as a cardinals fan, the trade that stings the most is giving up Sandy Alcantara and Zach Gallen for a few sub par Marcell Ozuna seasons

[@jimmyp410]

Regarding Robbie Ray, the difference must've been that much stickier Canadian "rosin".😂😂

[@zero213kt]

8:35 the poorly executed high five/fist bump. Jomboy would be proud

[@Cainb23]

pokemon music is awesome. i was so confused bc im hunting in lets go pikachu while watching this and i was like wtf that music isnt from this game where is that coming from

[@robadob55]

Side note. David Robertson is still racking up postseason innings. Dude is still a worthwhile arm

[@maxberglind3275]

Babe, wake up, jolly olive trade video

[@RSanchez111]

Nice pokemon music Jolly

[@michaelcornwall]

I was gonna comment wasn't Ramos the guy who got kidnapped, then you said it lol. Didn't realize he balled so hard

[@superjuddy]

I really enjoyed this video (especially as a salty Astros fan XD) I am curious though, how much do you consider the mets effectively paying the astros about 60M to take justin verlander back as a win? I know it's not easily comparable as prospects, and injuries have resulted but without him we don't make playoffs last year.

[@dumdawgpro]

cant tell until the prospects hit or not.

[@dumdawgpro]

i remember the edwin diaz trade as being a terrible trade... looks better now though

[@mpaulm]

Jose Bautista to the Jays for Robinzon Diaz in 2008 is probably the worst of all time. 37 WAR for 0.7 WAR😂

[@ligomi]

I still get upset whenever I even see the last name Capps. It's one of my top 3 most hated twins moves of the last 25 years

[@cmunoz2]

The ultimate goal in baseball is to win a World Series, not compiling more "value" that ultimately leads to nothing.

[@Trillyana]

3 teams have traded for Aroldis Chapman so far and 2 of them won the World Series the same year Can't argue with cold hard sabermetrics

[@josephjohnson5213]

The Aramis Ramirez and Kenny Lofton trade to the Cubs for Jose Hernandez and Bobby Hill in 2003 was as lopsided as it gets and wasn't even in the video 😳

[@dumdawgpro]

recent history*

[@ericnease1207]

Tyler Mahle to Minnesota, Spencer Steer and Christian Encarnacion-Strand to Cincinnati

[@WD--tw3zr]

In regards to the Chapman/Ragans deal... Flags. Fly. Forever.

[@zacszalka0808]

Not a trade but what EROD did to the tigers at the trade deadline was wild. Bro declined a deal to LA at the last second because of “leaving his family”. Like do you not want to be apart of the playoffs. Then bro signs to Arizona in the offseason 😩

[@YaBoyyJohnNBA]

The Rangers would love to have this version of Cole Ragans, but they're chilling with a World Series ring imo

[@theman1412]

The Verlander trade to Houston in 2017 was awful for Detroit

[@jacoblangguth5125]

I don’t think it was a deadline deal, but the reds traded one season of Alfredo Simon for Eugenio Suarez and then later a half season of Dan straily for Luis Castillo

[@zacszalka0808]

Michael Lorenzen got traded to Phillies at deadline didn’t pitch in postseason and gave up a gut that just made future game

[@isaacmartinez_]

Ragans never pitched this well with the Rangers and we won a ring because of it. Anti-Rangers bias runs deep at JM 😐

[@kylewardell8604]

The Reese Olson for Daniel Norris deadline deal is looking awful for Milwaukee

[@eastonlee832]

The Rangers don’t win the series without Chapman. While he wasn’t that good. He was serviceable and one of their main relievers that they used in high leverage spots last year.