The Curious Career of Jacoby Ellsbury

While his peak was one of the best by a center fielder in baseball history, Jacoby Ellsbury's career is mostly defined by his decision to play for his team's rival on one of the most head-scratching contracts ever handed out.
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.jomboymed...
Music (in order):
• Chill Synthwave - Digi...
• Summertime Love - LAKE...
• Moldy Lotion - Light f...
• Yuzzy - Running Wild |...
• Not Too Cray - Huma-Hu...
• Shadows - David Cutter...
• (FREE FOR PROFIT) Chil...
#mlb #redsox #yankees

[@SconnerStudios]

He's everything us Red Sox fans could possibly ask for. He won 2 world series titles, then became a free agent and cost the Yankees tens of millions for basically one meh season.

[@cejannuzi]

No in total he gave the NYY about 2.5 good baseball. I think that is about all they have got from Stanton too.

[@nightfall224]

⁠@@cejannuziLol Stanton has produced way more then Ellsbury for the Yankees.

[@joshuapatrick682]

I always thought it was obvious what he was doing in New York having come over from Boston...

[@isaacpeachey8609]

The baseball gods weren’t about to let him going to the Yankees slide.

[@robertbehof683]

So would that make Willson Contreras the Ellsbury 2.0 for the Cubs and Cards?? But, then again the reverse looks like Jason Hayward so yeah there’s that….

[@bpham-c9m]

Jacoby Ellsbury’s greatest contribution to the Red Sox was fleecing the Yankees like he did. Thanks for your service King 🫡

[@alperensengun6832]

They saw the Carl Crawford signing and said “let me do you one better”

[@inutero10]

Thanks for johnny damon though. 09!

[@rfe8nn2]

This is why we don't blame Henry Freezes for Selling Babe Ruth. He thought Babe Ruth would tank the Yankees.

[@prettygirlus9008]

@@alperensengun6832 Haha! Or, better yet, Dice-K.!

[@JabroniBaseball]

I always forget that he really did come in 2nd for MVP voting once

[@codyh9175]

Goated pfp

[@Trav81888]

I used to work in the Mets clubhouse. Spring training 2011 the guys in the clubhouse David Wright and his agents all player in a fantasy league that season. Had the draft at David’s sprint training house. One clubhouse attendant never played fantasy baseball he he didn’t know the league all that well. With his first round pick he picked Jacoby and we were all pissing our pants laughing. Welp, needless to say he got the last laugh that year

[@jaygq1543]

A broken clock is always right twice a day!

[@drtr3173]

Should’ve won that year too

[@JabroniBaseball]

@@codyh9175 I proclaim this, the summer of George!

[@alexw0310]

You forgot to mention that in 2007 he was the first taco hero of the "Steal a Base, Steal a Taco" campaign

[@venicemenace]

And thus he was dubbed “Tacoby Bellsbury”

[@andyzuleta5344]

Hell yeah I remember hahah ,I grabbed a 1 free Doritos taco near my old High school

[@seanconnors1613]

​​@andyzuleta5344 Doritos tacos didn't come out till 2012, unless you had crazy special Taco Bell near your high School dude❤

[@arok233]

a video on shane victorino "the flyin hawaiin" would be super cool!

[@anthonyemerson2965]

While (naturally) a lot of us Red Sox fans were upset he left for the Yankees, watching that contract turn into an albatross for the Yankees that ruined their payroll structure has turned him into even more of a cult hero than he would’ve been otherwise

[@nickschuman4652]

Always been a fan of Jacoby and those Red Sox teams. Also watching Corbin Carrol this year and trying to think of a comp, it’s Jacoby Ellsbury

[@KOCChristian]

Yeah as RedSox fan I had wipe my eyes make sure I wasn’t daydreaming good RedSox days, Corbin definitely going be what we always hope Jacoby would be.

[@maneyac16]

Still waiting on Jimmy & Jake to make that “Finding Jacoby Ellsbury” documentary

[@redmage08]

"winning the AL East handily" *shows them winning by 2 games*

[@SONICX1027]

Jacoby Ellsbury is a secret agent for the Red Sox by fleecing the Yankees, and I’m here for it. Also, I can see Jarren Duran as a Jacoby Ellsbury type player for the Red Sox, and that’s a plus

[@rancidcrawfish]

You really like leaving this comment

[@CHman712]

Scott Boras is a prick. But im glad the yankees ended up getting ellsbury. We all saw how well that worked. Haha

[@joshuapatrick682]

nothing "curious" about it.. he is a dedicated Red Soc who hates New York and so screwed them twice by taking their money and sandbagging his career to ensure NY wouldn't have a Championship with him on the roster.

[@astralflick]

Now I can’t wait for the Yankees to give Jarren Duran a $200million dollar deal in 2029

[@TheTEN24]

Big fan of Jacoby. Balled out against the Yankees and then did nothing for them lmao

[@stvinney]

I was so happy when he failed epically after signing w the evil empire It wasn't just about the money...for me anyway It was all about the money for him

[@Alan-rw3ez]

Okay this one really is a great confusion. Coming off an injury plagued season with only a .781 OPS and the yankees truly did believe they could regain that 2011 form again. They were so delusional and the rest of the league knew it.

[@redmage08]

Grew up a Red Sox fan, still love Jacoby. Deserves so much more love and honestly would love him to be a coach for the BoSox or the Dbacks(he lives in Phx metro iirc) in the future

[@chicagodude8888]

Don’t give massive contracts to guys entering their thirties. That’s the lesson to take from this.

[@LemonGlow99]

Ellsbury has a special place in my heart from growing up loving all the Boston guys from 2006-2013. Seeing him hit a homer off CC Sabathia at Fenway in 2011 is definitely a core memory and when he stole home off Andy Pettitte in 2009 my dad would not stop talking about it. Thanks for the blast from the past Jolly :)

[@prgnsean]

best steal of home ever! The look on Pettitte's steriod-using face was priceless!

[@rfe8nn2]

Jonny Damon hurt more for the RedSox then Ellsbury. Jonny Damon left after a first round sweep in 05 but Ellsbury it was right after the Sox 2013 championship. I think because Ellsbury left when he did it didn't hurt that much compared to when Damon left.

[@Tinil0]

Argh, that was the height of my baseball fandom man. I actually sorta fell away from baseball fandom right in 2013 (Nothing related to the team, just life issues). So many fond memories of that time.

[@dylanhammerle7848]

Bro ROBBED the Yankees

[@gabrielv.2647]

He reminded me alot of Grady Seizmore with the Indians. He balled out for the Sox, damn shame he didn't do it the same or better with the yanks.

[@GringoLokoMusic]

Saw him in 2018 rehabbing his hip in the facility in New York City. At that time they were still acting like he was on the way back. Never happened.

[@jdubmash]

Ellsbury basically single handedly won me my fantasy league yrs ago... dude was insane but couldn't ever get it going again... shame, dude was super talented

[@isaacgraham5727]

You know, the thing about Jacoby Ellsbury is that he was just never all that good, and it always felt like his success was… luck, or a fluke. Take those games in AA when he hit like .450 back in 2007 - I actually was at several of those games because the AA team in question was my hometown Portland Sea Dogs. And he was getting so goddamn lucky - pop-ups falling in, running out weakly hit ground balls, etc. I mean, I distinctly remember back in the 2007 postseason I was clamoring for Coco Crisp to continue to start in CF, because even though he couldn’t hit he played AMAZING defense and our two aces (Beckett and Schilling) were definitely strikeout/flyball guys, not groundballers. And I didn’t want a rookie barely out high A ball playing the most important OF position in the postseason. Of course I was totally wrong and Ellsbury was a star, but:… And even after that 2011 season, most every Red Sox fan knew that it was a fluke and we were just thrilled to have gotten what would obviously be a career year out of him. And then after 2013 I didn’t know a single Sox fan who expected or wanted to see him re-signed longterm - it was so incredibly obvious that his best was behind him, and that he was lucky to have done even that well.

[@nathanuber530]

Unpopular opinion, He should have won MVP in 2011. Cy Young is for best pitcher. No way he should have been snubbed like that

[@UltraKellonRealEstate]

The Yankees gave him the money they could've just given to Granderson 💯

[@jethrojacinto2798]

I knew it Jolly Olive is a CONFIRMED Red Sox hater 4:45

[@Setashi]

I will forever love Jacoby for his time at OSU.

[@hitmangfx7162]

This reminds me...Can I request a Scott Boras episode? Talk about a polarizing figure in MLB history.

[@HonkyTonkHellraiser]

Should have stayed in Boston. He went for the $ because if his agent Scott Boras

[@cejannuzi]

I think for the NYY he managed to play about 2.5 total good seasons of baseball . Just when we thought he might have recovered from the various issues--head injury, sore feet--his hip was shot. The same thing that got A-rod.

[@andyhighroller8217]

2011/2012, there was big rumors of a Lincecum for Ellsbury trade. Ellsbury was coming up on free agency, and Timmy was notorious for signing short term, high annual avg deals. Apparently both teams were scared they wouldn’t be able to retain them. Timmy was riding several 2yr/$44m deals, instead of taking 5-7yr deals the Giants would offer. Considering Timmy was a net negative for the SF 2014 WS team, and not extremely helpful in 2012’s WS run, having a Pagan/Ellsbury/Pence outfield would’ve been impressive, but perhaps having a Melky Cabrera/Ellsbury/Pagan outfield prevents SF from trading for Hunter Pence, a key figure for the Giants in years to come. Melky won the AS MVP, and would’ve won the batting title had he agreed to the Tony Gwynn Rule offer of adding an 0 for 1 at bat, but he refused and Posey got the batting title with an average nearly .020 below Melky’s. SF traded for Pence because Blanco & Shierholtz were playing a lot and not very well, but Blanco improved and 6 days after the trade deadline, Melky was suspended. Pence hit like .220 for the Giants during the remainder of 2012, but he was great in the playoffs & years to come. If they had Melky/Ellsbury/Pagan, they likely don’t trade for Pence, therefore the 2012 & 2014 World Series titles are up in the air, especially 2012’s, as they played a record number of elimination games en route to sweeping the Tigers(3-2 vs Reds, 4-3 vs Cardinals, 4-0 vs Tigers).

[@sethwoodhouse4797]

Ellsburys 2011 was just a fever dream I’m sure of it

[@FasuloA]

Matt Antonelli said that when he played with him at some point (cape league maybe?) he found out Jacoby used to chase deer on foot and had caught one before. I believe it.

[@sah4128]

Pirates legend Pedro Ciriaco

[@josefstein9062]

How the hell was Jay-Z Robinson Cano's agent? That is by far the most ridiculous thing I learned in this video

[@joel8692]

Jay z had just started a sports agency called roc Nation sports. His first clients were Dez Bryant, Kevin Durant, Miguel cotto, Robinson cano

[@matthewganong1730]

I was at the game in Boston against the White Sox when he broke the Red Sox single season steal record. A couple years later, by pure coincidence, I happened to be at a game the Red Sox played in Philadelphia when he broke the Sox single game record with 5 steals.

[@martinjohn9904]

He played hard and injuries took their toll. I'm glad he got his money! He was very exciting to watch if you liked baseball and were a Red Sox fan. He stole home on a number of occasions. Mookie Betts is the only other Red Sox I can remember even trying that.

[@Apere12]

I need a “how good was Jose Reyes”video that would be 🔥

[@FlyinTonite]

A guy with injury history and known for his speed getting older has so many red flags its not a major surprise he didnt work out with the yankees. It was sad to see but as a sox fan I only got to experience the good Ellsbury.

[@EnjoySackLunch]

Tacoby Bellsbury

[@clarissalion4777]

Jacoby Ellsbury is my favorite baseball player of all time. My mother and I are watching this. You've done such a wonderful job to capture his career. It's done so seamlessly. I love your sports/documentarian/news mix. The clips are so fluid. Your knowledge of your own sport shine through! Thank you ❤

[@alang353]

Thanks Jolly for reminding me of the horrors of Yankees Jacoby Ellsbury

[@cejannuzi]

I don't know. Until he hurt his hip, there seemed to some hope. Stanton makes me feel hopeless.

[@ByronGiant]

Why is Cursin' Snakes trying to deflect with a semi-passable East Virginian accent?

[@stephenthompson3348]

Scott Boras: I HAVE HAD ENOUGH OF TEAMS TANKING ❗️ ❗️❗️❗️❗️❗️ Some of ur clients are a reason to tank, buddy. Tough 💊 to swallow, champ

[@crazycano18]

Make a video on his former rookie team mate Dustin Pedroia. They kinda have the same fate lol

[@Alan-rw3ez]

If you compare the numbers they don’t do much, Pedroias WAR is almost twice as much.

[@t3hm4zn]

They don't have the same fate at all what do you mean

[@GTP2-zg9tn]

The Ellsbury Power shortage Phenomenon is NOT very unusual. We see it happen to many other players. And the reason is very simple. After signing a Massive Contract we see these players Batting Abilities Shrivel. Because they get off the PED's to avoid getting caught and losing their Gravy Train. When they become JUICELESS, they become USELESS!!! Two words to remember: Robinson Cano Don't you Know. Signing a professional Sport Contract can lead to Serious Life Style changing MONEY. So people will do whatever is necessary to land that kind of a Deal. It's just Human Nature. The constant Non-Contact Connective Tissue injuries are also indicative to PED use and Gross Over weight training at the gym. Never giving a body a chance to heal properly between weight training sessions.

[@carlpacquing2575]

I always remembered being scared every time Ellsbury would get on base. Whether it was an infield hit, or a double, he was guaranteed to wreak havoc on the base paths.

[@redsoxu571]

Extra factoids: -The 2007 WS was the first time Taco Bell ran their promotion of a free taco if/when the first stolen base of the series happened. Ellsbury grabbed that steal, earning the half-joking nickname "Tacoby" -Despite Ellsbury finishing 2007 as a rare combination of "proven" MLB performer who still had his full rookie eligibility, the Twins that offseason firmly insisted that any Red Sox trade package for Ellsbury include either Ellsbury or Clay Buchholz (whom similarly seemed to have proved himself while still retaining full rookie eligibility). I still remember how absurd this seemed at the time, as the Twins were *starting* packages with at least one even though counting Santana's surefire upcoming extension there was virtually no chance that he would be as net valuable to a team as either young talent. As an interesting bonus, the reported best offer by Boston would have worked out quite well for the Twins; meanwhile, after protracted pie in the sky demands dropped both the Red Sox and Yankees from the trade talks, the Twins were left to accept a package from the Mets that on paper was much weaker and, indeed, didn't amount to much (Carlos Gomez would eventually break out, six years later, but only after the Twins had moved him to the Brewers).

[@robertwoodcock222]

Lifelong citizen of Red Sox nation I have 3 Sox #9/#15/#2 ... Teddy Ballgame/Laser Show/Jacoby. First saw Coby play in HS, then lead Oregon State to the CWS then help the Sox win two titles and have one of the best offensive seasons ever that will be forgotten cuz too many shithead writers fail to grasp the the fairly simple concept ... Cy = Pitcher/MVP = Position player!!!!!!!!! Duh. Wanna win both, do both, just that simple!. Anyway, hated seeing him go to the dark side, but with Buttass as an agent provocateur I feared the worst and was not disappointed, seeing him don the con stripes was worse then Roger & Damon combined! But the combination of the lack of respect from Sox fans, the press and the front office and the eventual destructive nature of the move I've mellowed, forgiven and embraced him once again.

[@Kwolfx]

Jacoby Ellsbury was a highly questionable signing by the Yankees and his decline is not surprising. Ellsbury's only Mike Trout like year was in 2011. The rest of stats are nothing special. He did the Red Sox a favor by leaving

[@3verdades832]

He was on steroids like Chris Davis. Once they got paid they got off the roids and both fell off.

[@ChannelPerl]

Awesome video. He did indeed have a strange career. Was a super dynamic player but worn down by injuries. Cut from the same cloth as Grady Sizemore. Played the game like Lenny Dykstra or Damon to some extent but not as durable as those last two guys.

[@marksommers4179]

Ellsbury was a gutless player who collected money and stopped trying. While with the Red Sox, he was accused of milking his time on the injured list and only wanting to play if he was 100%. Youkilis and the rest of them were right about him.

[@lucasolson7045]

Seeing Jayson Werth in a Mariners hat seriously screwed with my head. How as a Mariners fan had I completely missed him playing for Seattle? He played in Tacoma, that's how...

[@XJapanGonnaGiveItToYa-cd4xj]

Jacoby Ellsbury didn't quite live up to the contract but he wasn't terrible either. If he wasn't a Yankee no one would ever be talking about this. You constantly hear about that contract. Compare to how often you hear about Shin Soo Choo's Ranger's deal.

[@mbodayle]

Makes me weary of the Yanks going after Cody Bellinger.

[@nathanmcguire932]

2010 MLB the Show Jacoby Ellisbury was so goddamn broken

[@dukedematteo1995]

Damon became a Yankee after the 2005 season. The RedSox were knocked out by the WhiteSox in the LDS.

[@ismaelgm13]

His injuries and basically going MIA from the game makes you forget how good this guy actually was. Jesus Cashman sure as shit questions himself from time to time on why he did not pay attention to the red Flags

[@robertheintze9413]

His unbelievable speed was what's curious?. Jim Thorpe reincarnated

[@texarican_77]

So if Acuña just finished with 41-73, could he reach a 50-50 season? That would be wild

[@jadprinz482]

Never wanted this clown. Cashman loves overpaying other teams players but always lowballs his own players. Cano should’ve been re signed.

[@matthewfogel3728]

As a Yankees fan that hated this signing, I can't tell if I'm super biased or this video underplayed his injuries and lack of contribution.easily one of the biggest busts for the Yankees this century

[@noahthomas4341]

Elsbeury was a moneyball player in a moneyball system. Poached to the jankees and didn't work out.

[@robertcrist6059]

Simple, listen to Foolish Bailey and don't pay for PAST performance.

[@asdfaeou]

I swear, Jolly banks so much Mets Flak at the office, then when it builds up enough, makes a video.

[@jgray2718]

Red Sox legend finishes career by destroying Yankees from within.

[@jonv1331]

Soooo Red Sox ellsbury is basically current day Evan Carter for the rangers

[@ethanbarksdale7524]

Wait a second….. I recognize the vape nation background music

[@mr.sa7anserv606]

He was a really exciting hardnose player and the fat lazy media savaged him every injury.

[@robertlasher9246]

Hey Red Sox fans. Do you guys hate or love this guy? He left your team but he fucked the Yankees lol

[@accelushyena3121]

Just another example of the Yankees paying useless players past their prime for their past successes.

[@m6cole]

Hey… Daniel Vogelbach is not fast!

[@michaellalli7693]

I’ll take Johnny Damon over Jacoby Ellsbury any day.

[@lewkyb]

⚾👍

[@seizuss]

hard watch only because he was my favorite player growing up

[@andrewfuryk7362]

Man is an infield single menace on MLB 2k13. Cost me a no hitter last night :(

[@Jeterfan906]

People always like to neglect the fact that he looked well worth the money prior to all the injuries

[@Ryan-zl3bn]

This is why mlb freeagent contracts usually suck

[@pabblo101]

As a Yankees fan, I lament this guy and our front office signing him.

[@stephens6912]

People despised him when he left Boston, and now he's a Red Sox hero of sorts for eating up so much of the Yankees' payroll. Just a wild turnaround

[@clarissalion4777]

I wore his 46 jersey and got hassled by my own city people. I didn't care lol. We all know he's Boston Strong ❤

[@YaBoyyJohnNBA]

Ellsbury really robbed the Yanks 💔

[@miken8889]

not a redsox fan, but ellsbury had a smooth swing

[@PSOpwnage]

Stealing all that money from NY makes him the greatest red Sox ever

[@Dylan.0010]

Us yankees should have learned from crawford and daisuke

[@bmposton98]

There’s gonna be a video like this on Kris Bryant one day.

[@KennyFrierson]

If he was more healthy I'm sure he would've been great

[@ParamoreFAV3]

He quit. I don’t care what anyone says.

[@loganmars2893]

you did Buster Posey dirty in that picture lmao

[@btk72491]

Love a Tim Locastro mention. Go Bombers!

[@richardmolinelli2953]

*Mets legend Tim Locastro

[@petespizzeriaabortionclini8020]

Him and Pedroia were a blast to watch especially hitting in front of Ortiz and Manny. God damn I miss those teams so much, great video as always Jolly!

[@Tinil0]

Don't forget Youk in there. That top 5 lineup was absolutely nutso man.

[@andersg1056]

Ellsbury was also a phenomenal college player

[@gusgarza6729]

The start of his career is eerily similar to Evan carter this year

[@spraynpray]

I didn't know he ever reappeared. I thought he abandonned baseball, got paid anyway, and disappeared.

[@jeikosalas5887]

My favorite player growing up

[@imandan1966]

Ellsbury is my fav Yankee of all time

[@bori1986]

Man what a sweet swing

[@brianbiechele1958]

Anyone ever been to Madras, OR? That is where he is from. An absolutely beautiful place. The Deschutes River runs by it. High desert. We are proud of him here in the Beaver 🦫 State.