The Best Win-Win Trades in MLB History

[@JollyOlive]

Maybe we do the biggest lose-lose trades next?

[@addisonharambe1576]

Carlos Beltran to the giants trade needs to be mentioned. That was a lose lose trade cause Beltran would move on next season and the prospect the giants traded was a major L. Zack wheeler was wasn’t all that good in Mets uni.

[@parkair_]

Joey Gallo trade to the Yankees gotta be on there

[@tyranttracergaming]

Loved this type of video, so do more trade videos!

[@octohoover]

Maybe Khalil Greene next

[@tylerfitzgerald266]

Idk if it's a loser trade, but one I'd like to see highlighted is when my Mariners traded our beloved manager Lou Pinella to the Devil Rays for Randy Wynn. How many other managers were traded for players? And how successful were those players after the trade?

[@jamesesterline]

10:07 It was actually the Padres' second pennant, they previously won the pennant in 1984

[@DerrickMims]

Yeah, I did a double take there when he said 1998 was San Diego’s first national league pennant.🤣

[@thedude3065]

and this guy calls himself a baseball fan?

[@bemhibbits4157]

Beat the Cubbies and ran into the Tiger buzzsaw in the WS...a team that started 35-5. Willie Hernandez, Trammel, Gibby, Morris...that team was epic.

[@ryanfox4462]

Gotta do the fact checks before publishing man...

[@chloewu2760]

@@thedude3065 dude's a mets fan , he's not gonna pay attention to any other team

[@scottbaldwin6763]

It was actually the Padres second pennant, they won it in ‘84, but lost to the Tigers in the WS.

[@TryPuttingItInRice]

Not a bad team to lose to. White Sox were pretty insane that year.

[@jennyanydots2389]

You are Wrong boy!! it was the Seahawks that beat them in the WS that year.

[@Publiclighthouse]

The odd thing about Kevin Brown is that he had no intention of playing baseball. Though he was a star pitcher in high school, he didn’t plan on playing when he went to Georgetown but rather focus on majoring in engineering. When the college baseball coach found out how good he was prior, he approached him several times about trying out. After being rebuffed, Brown eventually relented. He was a prickly personality but very talented.

[@MichaelDanger19]

Loved Adames when he was in Tampa Bay and glad to see him get his roses up in Milwaukee

[@kiefdemon1979]

I hear the name Derek Lee and my heart starts racing and the kid in me gets so excited. Took me back.

[@thedude3065]

New York trading Ahmed Rosario and Andres Gimenez for Francisco Lindor and Carlos Carrasco

[@ezridaxsgender3914]

Its kind of early to judge total value but that looks like it'll be on the next list if JO does another win-win vid in a couple years

[@DasHeisenberg]

Might as well add the Diaz for kelenic trade too

[@sliver01]

I can name three, Joc Pederson, Eddie Rosario, and Jorge Soler for the 2021 Atlanta Braves, Joc was the man for the NLDS, Eddie - MVP for the NLCS, and Jorge MVP for the World Series - and he hit the Moon shot that flew over the train tracks in game 6 that won it all for them

[@DT-xw9rr]

Win-win trade: Zach Greinke to Milwaukee in 2011 (?). Royals got Lorenzo Cain and Alcides Escobar, who would play a huge role in their 2014-15 run, and Brewers got Greinke as their ace

[@jackblasbalg7936]

Royals won that trade big time by a WAR perspective. Greinke put up 3.6 WAR in Milwaukee (Yuniesky Betancourt was also in that trade, put up -0.1 WAR. The package the royals received put up 32.4 WAR. I wouldn't say the Brewers lost the trade, but the Royals definitely won.

[@SmoothCriminal12]

Greinke also netted them Jean Segura later down the line as well.

[@Kurtle32]

Guardians and Mets trade as of right now seems like a win-win. The mets received Francisco Lindor and Carlos Carrasco which lindor has obviously been good but carrasco has been decent, and the Guardians received Gimenez, Rosario, and 2 other players that havent played for the Guardians yet but Gimenez has been great winning a gold glove hitting about .300 and 20 home runs last season and even finishing 6th for AL MVP last season and Amed Rosario has done really good as well and he got that nice speed and since 2021 Rosario has most triples and most games going 4/4 or better. I feel like the guardians actually won this trade but I typed all of this down and im not deleting it

[@alwillk]

Rosario actually sucks now, and is barely hanging in as utility player in tampa

[@PpP-dr1od]

The 2 trades that came to mind for me aren't particularly even in terms of WAR, but I think they accomplished the goals of both teams. -Phillies trading a package including Michael Bourn in exchange for Brad Lidge. Phillies don't win a WS w/out Lidge, but the Astros multiple 5+ WAR seasons from a gold glove CF, and even a good season from a reliever in the deal. -Mariners trade Randy Johnson to avoid paying him over injury concerns to the Astros for Freddy Garcia, Jon Halama, and Carlos Guillen. Neither side gets what Johnson does in Arizona, but Houston gets a historically great half season and Seattle gets 2 key pieces for their franchise's best season.

[@moreumbrellasplease]

I am glad someone brought up the Randy Johnson trade. He went on an absolute tear for the Astros. That was a talented team and it made sense for them to go all in for a World Series push. He pitched well in the playoffs - it just so happened they got run over by Kevin Brown. Seattle should have just paid him of course, but that is hindsight. They did well in that deal. Almost a Mookie Betts situation for them.

[@warface999999999999]

in my opinion, the DBacks/Marlins trade is a win/not lose. Jazz is solid, but Gallen is a bonafide ace. I bet Miami would rather have Gallen going forward

[@coilshredder]

As a Marlins fan, I can see both sides. Obviously Gallen would be nice to have, but outside of some mistakes in CF, Jazz's numbers are already incredible defensively. If he can settle down and get his hitting back to a better spot, this is 100% a win win trade

[@Narcandy]

I think this one is more win win than the Arraez trade. Pablo Lopez is definitely solid as well as pretty young and they additionally traded 2 additional prospects just for Arraez. Seems like a robbery from twins if any of those prospects pan out. I think its just more unlikely Arraez hits 330 year in and year out rather than multiple solid years from Lopez

[@Narcandy]

@@andrewtaylor995 typically I am with you. But a top end #1 ace who arguably is top 5 in the whole league is more valuable than an everyday player of Jazz’s calibre

[@Kubai]

@@coilshredder jazz is just an average overhyped baseball player imo

[@lexiescalderon5639]

@@Narcandy but jazz is a year younger and the year hasn’t ended so we don’t know what we’ll get from him, maybe he becomes an mvp in a couple and boom marlins win the trade, we’ll have to see. And with how the marlins are currently looking Gallen is not what where missing

[@pennyln]

The Chapman trade has to be up here. The cubs got Chapman which if they didn’t get him they likely wouldn’t have won the World Series. And the Yankees got gleyber torres aswell as other players. They also got Chapman back in the offseason

[@jacobbroene5337]

I would have inluded the three team trade that sent Ian kennedy to the diamondbacks, granderson to the yankees and scherzer to the tigers

[@Tyrunner0097]

Even if it was for a half-season rental, the Brewers trade for CC Sabathia was actually a win-win. CC got the Brewers into the 2008 playoffs, and Cleveland, even though the big prize of the trade, Matt LaPorta, was a bust, the 'player to be named later' would be Michael Brantley, who was a big part of Cleveland making the World Series in 2016.

[@Garrettcubed]

You always hear that if you win a world series it doesn't matter how much you give away. I would be interested in some lopsided trades that gave a team a world series. As a white sox fan the Adam Eaton and Chris Sale trades stand out to me.

[@TPTGopher]

As a Nats fan I was just about to write that the Giolito could be on here, because they don't win that World Series without Eaton (and I honestly think they would've won it in 2017 if he hadn't got hurt).

[@waltercampbell9787]

The Red Sox gave up essentially Moncada and Kopech who both busted for 2 seasons of elite Chris Sale (big reason they won 108 games and a World Series). I think the Red Sox have a slight edge on it just because in hindsight how bad the prospects actually were

[@HaydenP96]

Mariners trading Ketel Marte and Taijuan Walker to the Diamondbacks for Mitch Haniger, Jean Segura, and Zac Curtis worked out pretty well for both sides

[@SmoothCriminal12]

And Segura would then be flipped to Philly for JP Crawford.

[@justinlast2lastharder749]

Yes and no. The Diamondbacks clearly won it while the Mariners got useful pieces...but I think the Mariners playoffless streak ends earlier with Marte and Walker.

[@fluffskunk]

I've watched 4 baseball videos today, and every single one has reminded me of the 1995, 1997 or 2016 world series.

[@ryangale3757]

First win-win trade that came to mind for me was back in 09: Matt Joyce for Edwin Jackson. Both teams pretty much got exactly what they wanted out of that deal: the Rays got 10 WAR over parts of 6 seasons from a solidly league average starting OF on a team that struggled with offense (and even had an All Star 3+ WAR season in there), and while the Tigers only held onto Jackson for one year, they got the best season of his career (a nice 4ish WAR season in 09), then flipped him for, among others, Max Scherzer and Austin Jackson, who were key parts of their mid 2010s run of success. Have to think both sides came away feeling pretty good about those deals when it was all said and done.

[@gradywestling]

I’m surprised not a lot of people are talking about the Pablo Lopez/Luis Arraez trade in the offseason. Lopez became a fantastic pitcher and a regular starter for the Twins while Arraez had the best hitting season of his career for the Marlins, AND both these players helped both their teams make the playoffs this season. This is one of the few win-win trades I can think of.

[@jroggs85]

Absolutely. Both players flourished so much in 2023 after their trades and helped lead their teams to the playoffs after losing seasons the previous year, and it'll be very interesting to see how time affects the trade.

[@N394-l1f]

A good win/win trade was the Blue Jays trading Adam Lind to the Brewers for Marco Estrada. Estrada turned his career around in Toronto, and the Brewers traded Lind to Seattle for Freddy Peralta.

[@alexisborden3191]

Estrada was sneaky good in the 15-16 run. I always remember that team despite being made up of a lot of the same guys being a bunch of mashers in 15 and then in 16 the pitching just went off we got absurd seasons from JA Happ and Aaron Sanchez who both got CY votes. But Estrada was consistently pretty good both years and got votes in 15 I've just learned from his BRef page.

[@JordanRunge14]

The Brewers also received Trevor Richards who we flipped for our starting 1st baseman Rowdy Tellez

[@austinnistico3845]

Being there for that Juan Uribe walk-off at 5:37 is probably one of my best memories at a live game

[@crowtservo]

The best win-win trade I could think of for the Pittsburgh Pirates recently (since 2010) was the trade of Joel Hanrahan and Brock Holt to the Red Sox for Mark Melancon, Ivan DeJesus JR, Jerry Sands and Stolmy Pimentel. Brock Holt was worth about 8.6 WAR over his 7 seasons with the Boston Red Sox. Meanwhile, Mark Melancon was worth 8 WAR over his 4 seasons with the Pirates. The rest of the guys listed did almost nothing with their new teams. Hanrahan was the big piece going to the Red Sox and was hurt right away and his career was over. Brock Holt was a good enough position player during his time with the Red Sox. Melancon was the setup guy for the 2013 Pirates. The next year, he switched to closer when Jason Grilli was traded away. He had 51 saves in 2015 for the Pirates and was the best pitcher on one of the best bullpens in baseball. The Pirates traded Melancon in 2016 for Felipe Vazquez and the less said about him the better.

[@Joepelow1]

An idea for a lose lose video you could include the Troy tulowitzky trade

[@treypearson7706]

Still waiting on Forrest wall to pan out 😂

[@alexisborden3191]

Eh, Tulo was worth like 5 WAR over 250ish games in that 2 and a half years. Would much rather have him than Jose Reyes.

[@isaacbeynon533]

This was a fire video! I feel like looking at some of those super lop-sided trades would be fun/heartbreaking too - as a D-Backs fan I still can't believe the Dansby Swanson/Shelby Miller trade...

[@paysonfox88]

I don't recall if Roy Halladay was a free agent, or if he was traded from the Blue Jays to the Phillies. But the Jays got way better after that, and made back to back ALCS in 2015-16 after Roy left. The Phillies got more than they expected from Doc Halladay, and several playoff wins. That's a win-win.

[@ickybobclay26]

Dan Haren was one of my favorite pitchers cool to see him on here

[@asdfaeou]

That Kevin Brown on season bWAR is WILD.

[@rockofshame]

I think you can count trades as Win-Win even if there’s a war imbalance depending on the situation. If a trade for a rental player results in a deep playoff run, especially a championship, it’s well worth it imo even if the rental player doesn’t resign and the traded player remains good. Also, if a team has an excellent rotation but struggles at another position i think the war difference matters less, since you’re improving where you need it most.

[@pwnmasteh]

Love hearing about all these trades. Great vid Jolly.

[@Noseyy]

I’m so glad you started the video with the Willy Rasmussen trade instant subscription

[@itsmychannel]

Shoutout JP. Went to highschool with him. Nice to see him mentioned here

[@EpicInEd]

I’d like to give an honorable mention to the Red Sox and Blue Jays swapping Steve Pearce and Santiago Espinal. Red Sox get a guy who won World Series MVP as a rental, Jays get an All Star 2nd baseman who better lines up with their competitive window. Not sure what the WAR exchange is, but I think both teams do that trade again.

[@TheVlad1616]

Doyle Alexander for John Smoltz. Robby Alomar for Fred McGriff. Those are the 2 I think of when I was a kid and watched MLB.

[@topicbaseball]

10:07 it was the Padres second pennant, their first was in 1984

[@jamieshouldbeavailable]

I would say Alomar, Carter for Fernandez and mcgriff would be arguably one of the best trades in baseball history. If not for that trade the Jay's don't win back to back ws...

[@donnyamato3208]

You could do Justin Masterson from the Red Sox to Cleveland for Victor Martinez in 2009. Kind of obscure but as a long time Sox fan it stuck out to me. Plus I know you love the unique trades that aren’t as well known

[@jennyanydots2389]

Justin Masterson was a hockey player. Derp.

[@justinfowich6662]

Paul Konerko (from CIN) for Mike Cameron (from CWS) in 1999 is always the first trade that comes to mind when I think of win-win trades. The value the White Sox got is a no-brainer. Konerko played very well for them for 16 seasons. Mike Cameron was probably a better player, but the Sox needed a first baseman more than outfielders in the early 2000s with Frank Thomas moving to DH. Konerko didn't play well for the Reds, and they got a very good season out of Mike Cameron before trading him for Griffey. Seattle then got 18.4 bWAR out of him over 4 seasons.

[@tentoesdown8498]

Mariners trading Ketel Marte and Taijuan Walker for Mitch Haniger and Jean Segura was pretty fair

[@N394-l1f]

Mariners then traded Segura for JP Crawford

[@AndrewDeStJean]

I love listening to your videos while I drive, but more background noises always make me think it is something in my car

[@CycloneBurnesMusic]

I think the smallest win-win trade was the Steve Pearce for Santiago Espinal trade

[@1WrongOne]

I love the splits u show in ur videos to show players going nuts for certain amount of games

[@somekindofchris_]

Need part 2. Thanks!

[@TSteaktheNilla]

Thank you for reminding me how much we have never had a competent ownership group that had anything other than profits on their mind

[@willfrasure1348]

Marlins love a mutually beneficial trade they are so nice

[@warface999999999999]

also, the Padres won an NL Pennant in 1984

[@josephstepp6325]

I love videos like this

[@briannicasio9445]

More please. You could also do win-lose / lose-lose etc

[@rogerj21]

1:50 Actually Hunter Renfroe was the best overall hitter for MIL in 2022 but yeah...that was a Win-Win.

[@jakobhernandez6104]

1:52 “starting off 2023 strong” *shows 91 OPS+ and sub .700 OPS*

[@baller4621]

Was hoping you’d reference the Adames trade. I’m a brewers fan and it was a great example of win win

[@Extinguisher10]

Only a minute into this video, i would say that the Mariners flipping Randy Johnson to the Astros for Freddie Garcia, John Halama and Carlos Guillen should make this list.

[@iamhungey12345]

It depends on whom you ask since those thinking long term would give the W to the Mariners.

[@brandan7095]

Phillies angels was a win win. Marsh turned into a good hitter and ohoppe was doing great til he got injuried but is gonna be a solid player and one of the better hitting catchers

[@trevordunn3728]

I was at Cooperstown when the Cespdes trade happened I was pretty bummed cuz I always liked him

[@Madman27-g6e]

Jp firehydrant is wild

[@MTDubz619]

Hoffman for Sheffield worked out for both

[@utlonghorns104ever]

8:51 - Kind of funny hearing how Corbin is looked at as bad with the Nats while he was a vital player in the ‘19 World Series - obviously he has been bad since the WS (outside of ‘23?) but never would’ve won in ‘19 without him

[@tiffanygraybill4125]

If he didn’t include the gallen Chisholm trade I would have rioted

[@lurkintomgaming397]

I miss Josh Beckett and Jon Lester in the sox rotation. Those are the good ole days for me

[@danimal097521]

1998 was not San Diego's first NL pennant as stated at 10:10. They also went to the World Series in '84....

[@7srchoed]

I loved watching Kevin Brown

[@rorye6952]

Id be interested in some kind of "forgotten fleeces" video. Idk if thats feasible but like trades that turned out lopsided that nobody thinks about

[@RamReyez3]

What about the Padres and Astros trade that sent Caminiti to the Padres?

[@1WrongOne]

Loved these vids man. Like I watched sports center every day and every giants game but I ain’t never had no idea who Kevin brown

[@jamessommers2146]

Fun fact.. I actually grew up pretty close to J.P in Wisconsin

[@raz1683]

Huh, I now realised why I can't picture Dan Harren in one uni lol

[@kiefdemon1979]

How much do I love Drew Rasmussen? His name is a predictive text on my phone. Let's go Rays!!

[@UnderdawgMLB]

Wasn’t particularly close in terms of WAR, but the Cubs don’t win the World Series without Aroldis Chapman, and the Yankees get a solid player in Gleyber Torres

[@Speedster___]

Can you do a video on the biggest WAR swaps? Where combined war post trade (for contract years) was like over 35?

[@MrMansontaco]

The best win/win/win is the Tigers D-Backs Yankees. Scherzer Kennedy and Granderson would all lead their teams to the playoffs within 1 year of the trade

[@CallofHaloMC]

That Beckett trade for sure

[@illforever4153]

Mets fan pick Fulmer for Cespedes for sure lmao

[@legochickenguy4938]

I think the Harrison Bader for Jordan Montgomery trade has been a pretty good win-win for both sides, but they're both free agents at the end of this year so that story isn't entirely written yet.

[@jennyanydots2389]

Harrison Bader is a hockey player son.

[@Cinderbloxed]

would be cool to see a video on what makes a modern day pitcher effective at limiting hard contact

[@broncos435]

location probably (and control is a necessary precursor)

[@LiveFromThePorcelainPalace]

The greatest win-win trade in baseball history never happened. Not sure the year, but there's a story about the Yankees and Red Sox owners having a few drinks together and talking about their teams one winter. They got really drunk and ended up agreeing to a trade of Joe DiMaggio for Ted Williams... They stopped the trade when they sobered up the next morning. Now.. if that trade happened, it would have been a win for everyone involved. The Yankees, The Red Sox, and both hitters. Williams was a left handed hitter at Fenway, a park that favors right handed hitters... DiMaggio was a right handed hitter in Yankee Stadium.. which was a park that VASTLY favored left handed hitters (430 feet to the power alley in left field.. 360 in the RF power alley) Both hitters would have benefited from the change in parks and been even greater than they already were, and would have improved their new teams!

[@jamesgilmore69]

98' was not the padres first national league pennant, that would be 84'

[@darkwingdisk]

What about each teams longest players trade chain. Player A is on the team and was traded for Player B Player B traded for player c until you get to the drafted player

[@kartikfilm]

Greinke from KC to MIL for Lorenzo Cain and Alcides Escobar.

[@darealtpv]

JD Drew for Adam Wainwright 🤷‍♂️

[@kevhead1525]

John Franco for Randy Myers.

[@prettyboiiartistic]

We need a video on joba Chamberlain

[@DublinSeafoodInc]

Great video Jack

[@nox1ck589]

Derrek Lee Cubs legend

[@thomasjudge2623]

You said Kevin Brown helped the Padres win their first NL Pennant. They won the pennant in 1984

[@dafttassia1960]

Randy johnson to the astros strangely worked for both teams

[@coilshredder]

The Marlins are the kings of never winning a trade. It's either win-win or a massive L

[@huntergoldman4546]

The kelenic trade might be on here one day

[@Tir33nts343]

Lindor and carassco for gimenez Rosario and two prospects, win win for both

[@ob_gynkenobi4014]

Dammit. I was coming here to watch this thinking I wouldn't be reminded about the terrible trades the Pirates make.

[@brianbelden2449]

IMO 2007 Josh Beckett was the most single dominant season I've ever seen from a pitcher. 101 mph 4 seamer, a 98 mph 2 steamer, a 92 mph change up followed up with a filthy 12-6 and all within the AL EAST which was in a league of its own. Every single one of those AL East lineups was a mine field for any pitcher. Those lineups were brutal and it wasn't only NY & BOSTON. To this day I also think Schilling should have won the 2004 CY YOUNG award even though Santana had stronger numbers in the weakest division in the AL if not all of MLB.

[@iamhungey12345]

Weak competition or not it still doesn't change that Santana had better numbers in 2004.

[@Extinguisher10]

Kevin Brown threw the best heavy nall ive ever seen

[@austinfife8107]

I think you secretly love the dbacks

[@mattymutz6783]

Im sorry but the gallen chisolm trade isnt a win win at all. Gallen has a chance to be a cy young winner and jazz can barely bat over .220

[@Clynicxl]

BA isnt the end all be all for a hitters value just so you know

[@mattlentini5460]

I agree as of right now but there’s still a lot of time for improvement on jazz’s end

[@mattymutz6783]

@@Clynicxl you’re right it’s not. What about his sub .680 OPS and his lack luster center field defense? Or his .283 OBP

[@mattymutz6783]

@@Clynicxl what about his only 84 OPS+? He’s bringing negative value to his team. Idk why people defend him

[@Clynicxl]

@@mattymutz6783 im not defending him but dont try to sound smart like you know baseball when youre valuing a hitter by batting average 💀

[@Jimmersaunt]

The best trades benefit both teams.

[@jhaglili]

What about Granderson, Scherzer, Austin Jackson

[@OfficialNoob69]

great video

[@johndamario2546]

Rasmussen to the 60 day IL today lmao

[@natediscavage690]

Francisco Lindor for Andres Gimenez and Amed Rosario is looking pretty even for both sides

[@norwoodwildlife9849]

Plus in 2007 Mike Lowell won the World Series MVP

[@Jeterfan906]

Do some lose lose one’s next lol