The Best Win-Win Deadline Deals in Recent MLB History

Download the DraftKings Sportsbook app and use promo code OLIVE!
Sometimes, MLB trades work out exactly the way they should.
Thanks for watching! If you enjoyed, please leave a like and a comment, and subscribe to the channel! It really helps the channel grow and reach more fans!
Follow me on Twitter: / jolly_olive
and Instagram: / jollyolive_
Grab some merch: shop.jomboymedia.com/collecti...
Music (in order):
• Main Menu (2007) - MLB...
• Good morning - Amine M...
• Riviera - Smith The Mi...
• Summertime Love - LAKE...
Sources:
Dombrowski’s Trade Pursuits: www.inquirer.com/phillies/phi...
GAMBLING PROBLEM? CALL 1-800-GAMBLER (1-800-426-2537)
(AZ/CO/IA/IL/IN/KS/KY/LA/MD/ME/MI/NC/NJ/OH/OR/PA/TN/VA/VT/WV/WY), [phone] or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY).
Please Gamble Responsibly. Call 1-800-522-4700 (NH), 888-789-7777/visit ccpg.org (CT), or visit www.1800gambler.net (WV).
21+ (18+ KY/NH/WY). Physically present in AZ/CO/CT/IL/IN/IA/KS/KY/LA (select parishes)/MA/MD/ME/MI/NC/NJ/NY/OH/PA/TN/VA/VT/WV/WY only. Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. Min. $5 deposit. Min. $5 bet. Max. $150 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Ends 7/21/24 11:59 PM ET. Terms: dkng.co/dk-offer-terms. Sponsored by DK.
#mlb #phillies #angels

[@jacklongar4072]

You should do a "how tf did I get here" video where it's all players that don't look right in certain uniforms... like puig in Cleveland

[@BloomInTune]

If we're doing an all-time list, I'd put my vote for Reggie Jackson in an Orioles uniform for a season (which I think was only because the league vetoed the A's trade with the Yankees).

[@joekerUli]

@@BloomInTuneVlad in a rangers uniform.

[@tylerfitzgerald266]

Even tho it was huge for me at the time and I love my team, Cliff Lee in a Mariners uniform

[@chasebingaman]

Joey Bats and his entire tour of the NL East in 2018

[@roysreceptive]

Pedro and Glavine as NY Mets. Piazza and Big Hurt as Oakland A’s.

[@jamesesterline]

Not a deadline trade but an offseason one, during their fire sale after 2005 the Marlins sent Mike Lowell, Josh Beckett, and Guillermo Mota to the Red Sox for Hanley Ramírez, Aníbal Sánchez, Jesús Delgado, and Harvey García. While Mota was immediately traded afterward to Cleveland as part of a deal that got the Red Sox Coco Crisp, Lowell and Beckett would become part of Boston's core in the late 2000s and were key contributors for their 2007 World Series winning squad where both were All-Stars with Lowell finishing 5th in MVP voting as well as winning World Series MVP and Beckett finishing 2nd in Cy Young voting. As for the Marlins while Delgado and García only pitched a combined total of 10 games in their careers, Sánchez was a great pitcher during his time in Miami and threw a no-hitter for them in 2006, and Ramírez won the 2006 Rookie of the Year Award and became the face of the franchise for the next 7 years. The Red Sox got 32.9 bWAR from Beckett and Lowell during their time in Boston while the Marlins got 41 bWAR out of Sánchez and Ramírez when they were in Miami.

[@brandonblack_17]

Saturday doesn’t start until I get the Jolly Olive notification

[@Interviewsfromthebench]

Fr

[@themegjake4000]

We angels fans love O’Hoppe. It’s a great trade because we get to see Marsh(whom we also love) play meaningful baseball while also seeing a good catcher and team leader develop right in front of us. Not to mention, good catchers can have a huge effect on a team overall in a way other positions don’t.

[@yahcrack]

O’Hoppe is better than Marsh. As a Phillies fan, if we didn’t make it far since he’s been here, we’d be regretting the trade.

[@h4unt_]

@@yahcrackbut as he already said you guys already had your catcher situation situated with realmuto and will for a while, i dont see him going anywhere else

[@yahcrack]

@@h4unt_ should’ve kept him over Stubbs

[@graysonbuza1074]

​@@yahcrackok but you wouldn't have got someone of Marsh's ability for Stubbs

[@Siegprod18]

@@yahcrack we needed a better outfielder than odubel Herrera and we exactly got that in Marsh. Realmuto is hurt right now so that’s why Stubbs is playing but we wouldn’t have kept O’Hoppe because he is too good to be a backup catcher. Plus Marsh has been very good defensively and has improved offensively so we at least got some value for O’Hoppe.

[@redmage08]

This is the positivity the world needs Jolly thank you

[@maxteeth]

marsh feels so right for the phillies with his perpetually damp head. vibes unmatched. we love our swamp king. thank you angels

[@Lil_Pennsy]

We love marsh in Philly he’s been great for the daycare

[@DR.slzzzp]

FACTTTTTS

[@thepoisonouspotato3631]

As a HUGE Astros fan, I do miss him on the angels, but I was happy to see him in the World Series

[@marysaflorio7016]

I saw Brandon Marsh in the thumbnail and immediately put the video on. Not only is he really good defensively, but he’s also really likable. His positive energy is infectious.

[@StitchGames626VODs]

I’m very easy to click bait. I see Brandon marsh and I click

[@aaronjaiden62]

@@StitchGames626VODs me but with O’Hoppe

[@Rymann_23]

Jolly here's another win win trade that happened last year: Paul Sewald to the Dbacks Josh Rojas, Dominic Canzone and Ryan Bliss to the Mariners

[@ilovekatescott8057]

Nah the D'Backs won that trade

[@matthewgiusti7631]

@@ilovekatescott8057 rojas has been niiiiice

[@xeterh]

I loved Marsh but the Angels really needed a catcher. Like you said, our outfield situation let us trade Marsh and so far its been a lot of fun because Angels fans love O'Hoppe and Phillies fans love Marsh. I'll always tune into Phillies games to check up on Marsh.

[@ihatejschlatt]

The power pros music over the ad is chefs kiss, well done editor, good taste in music and games

[@Extinguisher10]

The Randy Johnson trade to the Astros. Astros got arguably the greatest 2 months any pitcher has ever had, and the Mariners got a top of the rotation pitcher in Freddie Garcia, a starting shortstop in Carlos Guillen and John Halama who bounced between the rotation and bullpen.

[@BSimms]

best series of videos right here

[@buckyjames1898]

God bless Jolly for calling the Phillies the most likeable team in baseball. Imagine you had to go throw up somewhere after saying that

[@MBustos828]

As an Angels fan I was really bummed letting Marsh go. That being said, I think O’Hoppe is the future of the franchise along with Neto.

[@Math.Bandit]

Not flashy in terms of WAR for either side but Steve Pearce for Santiago Espinal is a solid win/win imo. Sox got the WS MVP and Jays got a solid if not spectacular utility infielder to help stabilize and bridge to their next window.

[@natediscavage690]

Lose-Lose Trade from 2011 Cleveland: Ubaldo Jimenez Colorado: Drew Pomeranz (CLE #4), Alex White (CLE #2), Joe Gardner (CLE #8), and Mike McBride

[@graysonbuza1074]

Idk Jimenez was pretty good for Cleveland in 2013

[@natediscavage690]

@@graysonbuza1074 although they didn’t end up panning out for Colorado, when trading three of their top 10 prospects, they were definitely looking for more than a 2.0 WAR over three seasons

[@graysonbuza1074]

@@natediscavage690 I know just saying at the end of the day they got 2 WAR for nothing

[@futureddude4250]

The Brewers Royals trade that gave the Brewers Grenike and the Royals Escobar and Cain I think is a great win win trade as well, the Brewers got one of the best pitchers at the time while the Royals got 2 parts of their World Series core

[@shoukatsukai]

Rick Porcello 2016 and Bob Welch 1990 in the Cy Young mid-off (but winsss tho)

[@matthewsavage1932]

Might be a bit early but one could argue that the Arolis Chapman trade to the Rangers in exchange for Cole Ragans and Roni Cabrera was a win-win. The Rangers won the WS and the Royals got a Cy Young candidate and an 18 y/o prospect.

[@PpP-dr1od]

As a Phillies fan, I remember Buchholz the Diamondback...because he signed a one year deal with the Phillies the year before and immediately went down for the season. The season before Buccholz, the Phillies had another vet signed to a one year deal that had a year ending injury in April: Charlie Morton. Being a Phillies fan was rough for a while, but at least Buchholz didn't immediately win a WS upon leaving.

[@dominator8393]

Golly Jolly, these videos are the reason I wish I didn’t have to experience Sunday-Friday

[@theskipper34]

Talking about all those Angels players like Ward/Marsh/Adell/O'Hoppe/etc makes me hurt as a Salt Lake Bees native. Saw them all play here, and then they just disappear lol

[@grossla8053]

Double dipping on the Twins but I think both the Twins and Blue Jays are pretty happy with the Jose Berrios trade. SWR is a stud and Austin Martin should be a good utility player for years to come.

[@EthanRKassel]

A few weeks before that Twins-DBacks trade, I saw all three of those prospects play in a game between Kane County and Cedar Rapids! Wonder if scouting that day played a part.

[@DigDug500]

Legendary Happy Grape return

[@michaelgarman3750]

Cole Ragans for Aroldis Chapman was Win:Win. KC gets their Ace, TEX gets their WS bullpen piece they dearly needed

[@benmuschol1445]

Time will tell but I'd argue the Adames Rasmussen trade between the rays and brewers was win/win. Obviously the reason the rays wanted to deal a good shortstop has... changed. But Rasmussen was killer before his injury and I don't think rays fans or brewers fans are upset with the trade

[@GwresYnKernow]

Oh god, that Rick Porcello Cy Young. :D

[@Gravy_Jones22]

Imagine being a Mets fan and calling the Phillies "the most likeable team in baseball."

[@TiagoGomez-hb9te]

True

[@jacobouellette4430]

I think a super under-rated lopsided trade is the trade that sent Heath Hembree and Brandon Workman to Philadelphia for Nick Pivetta and Connor Seabold. Hembree and Workman in their time with the Phillies had a ERA+ of 37 and 66 respectively, and though in 2020, Pivetta did have a 42 ERA+, since then, he has been right around a league average player.

[@danielradomile8526]

I’d argue the J.P. Crawford from Philly trade there were a few pieces in that trade that don’t really matter and Carlos Santana but J.P. Has become there guy in Seattle and Jean segura played some incredible years in Philly helping with their first World Series run

[@yamuthastwat123]

I’d even say they’d be a lot closer in numbers as far as that bWAR reference if O’Hoppe didn’t get injured last season, kid is already a stud as an angels fan there is pain but sometimes there’s good in that pain and our 25u guys are the good rn

[@gunnardsippert4094]

4:54 La Tortuga sighting 🐢

[@vandy2269]

Another great one is Chapman for Ragans

[@jacobschumacher6987]

What’s more fun is that the Tigers had an offer for baby Alex Bregman for Fulmer in (I believe) 2016

[@timothylee2902]

Mariners and diamond backs, Mitch hangar and Jean segura for Ketel marte and taijuan walker

[@gerardfrasier3935]

As a coaster enthusiast, I love the Kingda Ka reference

[@Leafgreen1976]

Feel better,Olive.Sounds like you were a little under the weather in this one.

[@JollyOlive]

Thank you! I certainly was

[@wilbert3842]

10:29 a popstar on the field with Cespedes no wonder why the tigers were sellers at the deadline

[@robertedmiston6348]

What about the Willy Adames for J.P. Fiereisen and Drew Rasmussen as a win win trade done a little before the deadline?

[@colingentry296]

Ragans for Chapman swap will go down as one of the best win win trades

[@stevengarrison1019]

Do one of trades that were talked about but didn't happen

[@Fatjack1]

Power pros music hits hard

[@Jeterfan906]

I still think the A’s win a World Series if they didn’t trade Cespedes. It didn’t make sense at the time and it doesn’t make sense now. They didn’t need more pitching, they were a worse team with Lester, and then they went from virtually having the division locked up to losing the wild card game

[@matthewgiusti7631]

2014 giants traded Heath Hembree to Boston for Jake Peavy. win win. both pitchers won World Series with their new teams

[@victormorillo_006]

Did the Yankees-Cub make the cut for the next video? The Yankees acquired Aroldis Chapman for 4 guys that are now retired on 12/28/15 now, what’s next is a situation that I brought up A LOT on Mets social media I participate on. I was saying at the time that if the Mets struggle they can trade Pete Alonso, JD Martinez and attempt to sign them in the offseason. It was done before. The Yankees traded Aroldis Chapman 7 months later for Billy Mckinney (Cubs 6) , Adam Warren (Vet), Rashaad Crawford (not ranked) and Gleyber Torres (Cubs 1) haven’t check their contribution but Aroldis pitched to a 1.01ERA in 29 innings, helped the cubs and himself to win their WS championship, then he signed with the Yankees in the offseason. If I didn’t fall in love with the Mets first, the cubs would have been my team. Super passionate long suffering fans well deserving of a ring. Whenever Chapman, Rizzo etc retire they will always be remembered in Chicago. Whatever those 3 players gave to the Yankees, doesn’t compare to what the cubs got in that trade. I say is even.

[@Jmazz]

Superstar Brandon Marsh mentioned

[@andrewstoloff600]

Chapman for Torres in 2016 is definitely win-win

[@mariogasparri9452]

Jazz chisholm for zac gallen

[@karlapants]

Mets fan here…thank you for the end of this episode

[@matthewgiusti7631]

2019 giants traded Drew Pomeranz for Mauricio Dubon. total win win trade

[@JohnsonMcGee69]

4:58 JOEY WENDLE RAHHHHHH

[@josephkrebs6906]

Jolly I just wanna say, I did indeed say something when u asked to be a Mets fan for a seconf

[@OhhMyyDogg]

How about breaking down Tim Wakefields early career up to his breakout in 1995?

[@kylebittner1327]

Is Chapman to the Cubs for Torres considered a win win?

[@markzuckergecko621]

Depends on the season. Lol. Gleyber has been great, and he's also been terrible. And Chapman was just a rental, but they won their only world series of this millennia. Can't argue with those results.

[@zackpatton6233]

Darin ruff for JD davis was a snub

[@Tommy_11812]

Do Monty for Harrison Bader

[@hepatitiscyalater7269]

Wasn’t win win

[@mitchellsanchez3937]

Although I loved Eduardo Escobar on the Dbacks, trading him for Duran wasn’t the best move

[@theyeetman2.071]

Happy grape lol

[@DR.slzzzp]

talking about a SEPTEMBER collapse while wearing a NY hat had me dying but for different reasons…. my brain is broke

[@Noseyy]

Drew Rasmussen for Willy Adames on next episode

[@kyle666man]

8:33 I’m a Mets fan, and being a Mets fan makes ME nauseous.

[@PrazMaster]

Feel like the Cubs/Phillies swap of David Robertson for Ben Brown should’ve made this.

[@BradyI-zp5qn]

I think Brewers and Rays trade for Willy Adames is the ultimate win win trade

[@burgerhamlinklog312]

Logan O’Hoppe mentioned

[@DR.slzzzp]

as a phills fan, i miss him & moniak

[@Kin-vc5wo]

Eaton to the nationals trade? Even the Sox did nothing with what they got back

[@goathippo93]

Technically, Cespedes was already donning the orange and blue when he was in Detroit

[@OH_MY_DOGGG]

You think teams arent trying to rob each other Bless your soul.

[@Manbearbull]

I see what you did. Start with a Phillies trade, shit on the mets half way through. i approve

[@TheOsiruss]

“Most likeable team in baseball” is a stretch for the Phillies

[@windyharp6402]

I LOVE BRANDON MARSH SM

[@Blackwingdesigns]

I'm a Rays fan (yes we exist) but I'm speaking from experience wanting loved players move to other teams. Please Angels get good like soon or trade Mike Trout. I don't say this out of spite for the Angels or their fans. I would love nothing more for them to be good and have him in the playoffs. But as it stands he'd getting old and needs to be playing relevant baseball and post season games. He's not only an Angel but belongs to Baseball. It would be a shame to see his career wasted.

[@benjohnson_35]

POWER PROS

[@c_s_b_9_4]

Logan "Makes Me S" O'Happy

[@katieg2449]

woah short hair Brandon Marsh jumpscare

[@cro4194]

sheesh

[@nicksmith161]

obligatory MLB POWER PROS MUSIC comment

[@pikapikachu8694]

パワプロのBGMやん

[@thiccbricc2106]

im still waiting for the day they finally make another english copy 😥

[@chasecarpenter4019]

#mets

[@trcogs]

Come home Eddy Escobar… come home…

[@adriansym]

Rest in peace khyree Jackson 😞

[@BayAreaBlues]

As a ducks fan this hurt man 😔

[@stonecanady3026]

First

[@samujiro8729]

I LOVE BRANDON MARSH❤❤

[@TheNMan64]

"Most likable" team is a very VERY refutable claim

[@Haha_You_Fool]

No, he cooked

[@hellsinvader]

40 minutes and under 3,000 views. Jolly fell off

[@yahcrack]

O’Hoppe is better than Marsh. We should’ve kept him.

[@Haha_You_Fool]

Literally never would see playing time with JT existing, plus Marsh is still really good

[@gabegarner32]

Day 1 asking for a Corey Hart video

[@futureddude4250]

The Brewers Royals trade that gave the Brewers Grenike and the Royals Escobar and Cain I think is a great win win trade as well, the Brewers got one of the best pitchers at the time while the Royals got 2 parts of their World Series core