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.jomboymedia.com/collecti...
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….

[@brianpham748]

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.!

[@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

[@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!

[@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

[@SaltoDaKid]

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.

[@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.

[@maneyac16]

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

[@Setashi]

I will forever love Jacoby for his time at OSU.

[@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

[@OH_MY_DOGGG]

I remember where I was when Jacoby went from first to third on a wild pitch. That was his first big moment.

[@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

[@jackmckean6246]

Jolly Olive has been my favorite KZbinr for the last year 🐐

[@firelordgeoscientist619]

Thank you, he was my favorite player and one of the reasons i became a Red Sox fan. His 2011 was historic

[@LordJudgement1818]

Ellsbury is one of my dudes! loved that guy. Loved seeing him ball out in college when he kept bringing Oregon state beavers

[@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.

[@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

[@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.

[@SteamboatMack]

Interesting stuff! Thanks Jolly

[@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).

[@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.

[@jacobzura]

my jacoby ellsbury jersey i ordered came in the mail yesterday and now this video drops

[@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.

[@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.

[@brianbiechele1908]

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.

[@TheTEN24]

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

[@redmage08]

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

[@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.

[@albertlopez2482]

One of the funniest videos I’ve seen from Johnny Olive

[@unkledoda420]

There are so many guys from that mid 2000's- mid 2010's era that had potential for amazing, possibly even HoF careers but the injury bug got 'em all. Ellsbury, Morneau, Pedroia, Wright, Fielder, Hafner, Sizemore, Tulo, Lincecum, Hamilton, I'm sure there's another dozen or two I'm forgetting. It's really a shame.

[@mr.satanserv6067]

Hamilton was a drug addict.

[@RetiredJB55]

great content

[@jeikosalas5887]

My favorite player growing up

[@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...

[@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.

[@richiepoppin]

So glad you are bringing this up it's like he never existed in the Yankees universe they never mentioned ever again 😆

[@pabblo101]

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

[@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.

[@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.

[@Apere12]

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

[@sethwoodhouse4797]

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

[@bori1986]

Man what a sweet swing

[@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.

[@jillargos7729]

excellent

[@jgray2718]

3:30 I do like that game. My first thought seeing that list was "Huh, I thought Scott Podsednik was pretty slow. Guess I remembered that wrong."

[@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).

[@dominiczipfel5317]

i remember there being like 50 games where him and gardner were an absolute FORCE at the top of the lineup. Just 40 games

[@ericwalsh4881]

i remember him signing in new york after we (seattle) signed cano.

[@sah4128]

Pirates legend Pedro Ciriaco

[@astralflick]

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

[@btk72491]

Love a Tim Locastro mention. Go Bombers!

[@andersg1056]

Ellsbury was also a phenomenal college player

[@23CJ94]

Ellsbury is one of my top 5 favorite Redsox players so when he signed with the Yankees, I was devastated. But then he barely played for them after acouple seasons and then I just laugh at the situation now

[@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.

[@joelgordon6181]

2:42 God of Joy reference goes crazy

[@jethrojacinto2798]

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

[@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

[@hitmangfx7162]

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

[@andrewfuryk7362]

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

[@deprosport7254]

I’m still bitter to this day about Jacoby losing that MVP to Verlander. One of the greatest seasons we’ve ever see by a position player shouldn’t go forgotten like that when pitchers already have their own MVP award. Great video Jolly.

[@coreygilliam8533]

Juan Pierre was so underrated. Hall of Fame player in my opinion.

[@davidgraney3413]

Love the Tim Lacastro ref

[@nickuber2573]

One of my favorite red sox players ever.... broke my heart when he went to the yankees.

[@imandan1966]

Ellsbury is my fav Yankee of all time

[@PFBM86]

Johnny Damon didn't leave the Red Sox right after winning the world series, he left a year later after the 2005 season

[@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.

[@dannyvelez1012]

God damn you for this video but thank you very much

[@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

[@texarican_77]

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

[@yankees2864]

I just had a moment of rage reading that name

[@tyberiksen]

Red Sox legend even when he was wearing a different jersey. Earned every penny of the 153m.

[@e.ramaenqvist9573]

Right on Bro 🐕🐕🐕🐕🐕🐕🦁🦁🦁🦁🦁

[@Jeterfan906]

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

[@asdfaeou]

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

[@loganmars2893]

you did Buster Posey dirty in that picture lmao

[@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

[@miken8889]

not a redsox fan, but ellsbury had a smooth swing

[@seizuss]

hard watch only because he was my favorite player growing up

[@dukedematteo1995]

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

[@chicagodude8888]

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

[@xxSLAV33xx]

How is Ohtani not on the list for guys with more fWAR in a single season? Is it strictly a position player list or am I missing something?

[@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

[@dominic64tblightning24]

He should've won that MVP honestly

[@ethanbarksdale7524]

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

[@lewkyb]

⚾👍

[@jonv1331]

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

[@severianthefool7233]

I need more southern Jake in my life

[@EnjoySackLunch]

Tacoby Bellsbury

[@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.

[@gusgarza6729]

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

[@nathanmcguire932]

2010 MLB the Show Jacoby Ellisbury was so goddamn broken

[@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.

[@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

[@CameronBrown123]

I love u jolly

[@cecagna]

I'll always like Ellsbury and Damon. I'll never begrudge former successful Sox players who end up going to NY for a paycheck. He helped bring titles to my city in my formative years, and I'll always remember that. Guys copied his stance, girls put up posters of him. I hope his body has fully recovered from (what I consider) a great career in professional baseball.

[@thewisemanpaul]

LOCASTRO MENTIONED

[@danflaherty1861]

Being a kid whose favorite player was Jacoby Ellsbury was an early lesson in heartbreak

[@bmposton98]

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

[@Snazzeo]

Wolly Wolive

[@UltraKellonRealEstate]

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