Worst Contract Extensions in Baseball History

Twitter: / dead_baseball

[@trevormaymusic]

Vinny Castilla being “induced” into the Mexican Baseball HOF has be rolling over here 😂

[@warlordofbritannia]

It has me kicking and screaming

[@tastyneck]

For reals.

[@BaseballsNotDead]

Oopsies.

[@Jose_Hunters_EWF_Remixes]

has *_be_* rolling? I'm shocked and horrified by pronunciation Nazis Most especially because I was certain I would be the only one who noticed/commented on this

[@MoeBergOSS]

@@Jose_Hunters_EWF_Remixes Ssshhh Don’t be a racist Pedro.

[@pesky716]

Morneau’s concussion changed everything. The most heartbreaking “What If” as a Twins fan. He is still VERY much loved here.

[@ryanm4013]

He is loved all over. He always seemed to be a great guy and a great player who never seemed like he was just going through the motions.

[@dustinbell401]

🇨🇦

[@mpaulm]

“If Howard is worth $25 million/year, Pujols is worth $50 million/year.” I’ll never forget Larussa saying that.

[@jasonanderson5034]

what about me im i worth attleas 10 dollars a year could a mlb owner just buy me 10 dollars worth of juice and i will show up for pratice and play if they want me to in games

[@doormat2539]

Highest quality of statistic analysis on KZbin combined with entertainment. Baseballs not dead your videos are amazing

[@BaseballsNotDead]

Thanks!

[@WC6]

the Danks extension is *still* the 3rd-largest contract given out in White Sox history. It's Benintendi's 5/75M, Moncada's 5/70M, then Danks. Imagine what that team could do with a real owner.

[@travisp5747]

Still can’t comprehend the Benintendi one lol

[@BleedBoston]

That’s pretty wild 😂😂 and I thought the Red Sox ownership lack of spending was bad

[@warlordofbritannia]

I started following baseball in 2007. Willis’s coming down with Steve Blass disease is the first time I became aware of how quickly pitchers can disappear.

[@Karmy.]

At least we got Miggy in the same trade so the Dtrain derailing wasn't that huge of a deal

[@SamtheBravesFan]

I think Willis's problem was just that he was unable to repeat his high-leg kick delivery as he aged. As he progressed in his career, the kick became much less exaggerated.

[@SmoothCriminal12]

​@@SamtheBravesFanwhich wasn't helped by the fact that Jack Mckeon really overused him his first three seasons.

[@HeyItsJoeB]

As a Yankees fan I felt bad for Hicks. Never wanted him to fail and I’m glad he found it again in Baltimore.

[@edgarmanuelzetinaaguilar6972]

He was a top CF while healthy, he was never the same after the injuries. Smh. I remember him making that catch in the game against the Twins.

[@XJapanGonnaGiveItToYa-cd4xj]

Dennis Martínez...we still love El Presidente in Baltimore but yeah he was a big part of the team's collapse in the mid 80s despite "on paper" rosters that were amazing. Scott McGregor's arm blowing up was really bad too.

[@DansbySwanson-xp2zf]

Most underrated baseball KZbin channel

[@BaseballsNotDead]

Thanks!

[@gadzooks5398]

What's worse about that Bailey contract was that they had a choice going into the 2013 offseason... extend Homer or extend Johnny Cueto. They extended Homer and then watched Cueto win 20 games in 2014, lead the NL in Ks, and finish 2nd in Cy Young voting, ensuring there was no chance Cueto wasn't leaving in free agency after 2015. So, the Reds had no leverage in subsequent trade talks and the only thing they got back from that deal was... watching Johnny Cueto win a World Series for another team. The Reds are just now recovering from that Bailey extension.

[@ryanm4013]

I thank you for Cueto!!!

[@SmoothCriminal12]

And Cueto was also coming off a fourth place finish in Cy Young voting in 2012. Only defense I can give is maybe Cincy got scared of potential injury issues down the road after losing him in the NLDS, but clearly that didn't hurt him long term.

[@Mizoo1992]

These videos you do on contracts are so fascinating. You always go the distance to get the math correct. You give us a visual number to see how bad/great a contract is. A little over month till opening day!

[@BaseballsNotDead]

My pleasure!

[@smoceany9478]

immediately stopped what i was doing to watch this

[@DansbySwanson-xp2zf]

Same

[@jontafferofficial]

you called it with hicks, he is indeed with the angels!! hahah

[@devlinjointz4754]

That Simpsons reference was gold too

[@MrRenner12]

Babe wake up, another Baseball’s Not Dead video just dropped

[@GeeEm1313]

No way! Babe Ruth is at your house?

[@thruyou]

He'd only know you said this if he existed and was currently looking at the comments on this video

[@rancidcrawfish]

I don't think he cares about worn out, reused yt comments

[@EthanNiedorowski]

No babe either way

[@unkledoda420]

Aaron Hicks was signed by the Angels a couple of weeks ago.

[@BaseballsNotDead]

One day after I recorded that audio.

[@antonioreconquistador]

Matt Harveyesque deal. How much on the minor league contract?

[@davidleatherberry4122]

Baseball's Not Dead and Jolly Olive both make such superb baseball content, keep up the great work!

[@BaseballsNotDead]

Thanks!

[@impairedthoughts4701]

Nothing like breakfast and coffee to go with Baseball's Not Dead😊

[@Draconisrex1]

I'm glad you had Zito on your FA contracts. There are still Giants fans that think it was great because he had a few good games in the playoffs...

[@Molorange]

That fan caught that Baltimore home run against Danks with his chest lol that had to hurt

[@travisp5747]

Lmao hell yeah. Looks like it could potentially of been an April game so you know it’s probably in the 40s or 30s as well. Can’t imagine lol

[@hitmangfx7162]

Nice dunk on Mike Lansing. That drop in power is mind blowing.

[@jpal1486]

Preston Wilson did pretty well in those 58 more games with the Cardinals. He even got himself a ring like his pops did 20 years prior. Maybe he got paid too much, but oh well. For the 2006 Cardinals though, he was priceless. Provided solid offense and defense off the bench with some decent starts as well. You can knock the contract but not the player bro!

[@claytons3654]

I am SHOCKED that Rougned Odor didn't make this list somewhere

[@CompletelyNormal]

It's weird seeing any "worst of" lists without any Mariners on it.

[@msu15]

I'm a Yankees fan and I'll never forget when I saw the ESPN headline about the Hicks' extension. I yelled out in the office, "NO!! WHY!? What are we doing!?". My boss came over and thought something was wrong and then just started busting out laughing. That was an incredibly stupid decision by Brian Cashman.

[@StevePods13]

The level of excitement I get with these uploads. Best intro music in all of KZbin.

[@BoondockBrony]

I remember so many of these guys as a kid. Especially those Rockies players.

[@ShrexyGuy]

Seeing Morneau on this list is jarring, even as a yankee fan

[@antonioreconquistador]

First basemen get the shaft by WAR despite holding their own in an oft-involved position. Kinda because of the average stats per position.

[@XenoMonicals]

I always love these videos Mostly because I learn about players that I've never heard of before that I figured I should know about

[@patrickmoreau7592]

I’m glad when you point out when injuries played a big factor Good video

[@TheRealBatBoyAlive]

I will admit that I was surprised to see Bonderman in this list.

[@Karmy.]

Same

[@warlordofbritannia]

Really? That one was infamous back in the day

[@jordanleighton6893]

21:52 It hurt, as a brewers fan, to see one of my favorite players from that era on this list

[@jamesknapp64]

8:42 that perfect Game is my first memory of watching MLB highlights on ESPN.

[@jamesoost6948]

matt kemp was still very productive offensively through most of this contract if the dh had been a thing in nl early in this deal his value would look significantly different

[@psychokittytv4530]

Such a great video, love it. Just a FYI, the LA Angels got rid of the "of Anaheim" in 2015. Just thought you should know since it's been basically a decade. Don't want to get a big league name wrong after 9 years and all.

[@warlordofbritannia]

Sometimes I still say Florida Marlins

[@warlordofbritannia]

@@lnodlt173 Nah, they should be the Los Angeles, California Angels of Anaheim

[@psychokittytv4530]

@lnodlt173 it is dumb, but it's like saying SoFi Stadium isn't in LA. It's in Inglewood. Inglewood is 19 miles away from LA. Anaheim is 25 miles away. It's the LA area, that's just how it works. You don't get Anaheim news, you get LA news.

[@psychokittytv4530]

@lnodlt173 maybe it should be the Inglewood Rams and the Inglewood Chargers. Or maybe the New York Giants and Jets should be the New Jersey Giants and Jets

[@tastyneck]

Another great vid. These are always super interesting, so keep up the good work!

[@BaseballsNotDead]

Thanks a ton!

[@BakaBroski]

You know it's a great joke when you immediately go "Oh god..." and want to die after saying it lmao

[@treytackett1209]

Love your channel bro, i look forward to every vid. Please keep it up!

[@BaseballsNotDead]

Thanks! Will do!

[@mattvargashasyourback]

I can’t think of a better intro on KZbin seriously

[@TheTEN24]

always enjoy your content bro keep it coming

[@SalvoSLR]

I’ve been anticipating this topic, eager to watch

[@JolsonTube]

Finally, a list the AL central dominates

[@ryanm4013]

😂😂😂

[@jediknightfalcon]

Would love a video of the worst pitching years in baseball history, maybe mention injured seasons but mostly healthy i think could be interesting

[@JarettGray1604]

As a Braves fan I was never mad at Dan Uggla. Dude played his ass off and always hustled. Class act

[@avandelayy9089]

I fell to my knees in Walmart when I got the video notification

[@sleazye7638]

Another banger as always, keep up the awesome work!

[@BaseballsNotDead]

Thanks! Will do!

[@joshuapatrick682]

Dan Petry made 6 million playing baseball in the 80's. That's back when 6 million dollars meant you were actually rich.

[@evanblakeley7732]

I’m a little late to the vid but you genuinely have my favorite intro of any channel on KZbin

[@Touchmahtoaster]

You have a great voice for doing commentary, great video

[@BaseballsNotDead]

Thank you kindly!

[@johnnycashbenham1192]

As a Yankees fan, i never understood why they gave hicks that extension, he showed flashes of being a great player, but not enough for a 7 year deal 🤦‍♂️I'm so glad they got rid of him

[@francoiscorpel8304]

Love the video! Pretty sure Hicks signed with the Angels a couple weeks ago. Also very frustrated to see my Tigers a bunch on here

[@BaseballsNotDead]

"Pretty sure Hicks signed with the Angels a couple weeks ago." It was literally the day after I recorded the audio.

[@francoiscorpel8304]

@@BaseballsNotDead Ah damn, gotta love how that works out sometimes

[@matsuiforever25]

Admittedly, I am one of those Yankees fans who may have (unfairly??) developed an intense distaste for Aaron Hicks. But, saying that his 2022 was slightly below average seems kinda generous. There! Bitterness unleashed Another killer video from BND!!

[@aeroburn5665]

Aaron Hicks' contract terrorized me while he was on the Yankees but at least he gave us some great moments (especially against the Twins)

[@Quanic2000]

Aaron Hicks career high batting average was .275 with the Orioles after the Yankees let him go. Let's not act like he was 2022 Matt Carpenter 😂

[@Bajirkus]

Admittedly for Vinny Castilla, showing him striking out to 2000 Pedro Martinez just shows that he's a mortal being.

[@travisp5747]

On the dirty Pedro yo-yo

[@reyesjosh67]

Amazing video amazing Channel baseball is back baby

[@BaseballsNotDead]

Thanks!

[@UHOH_415]

The funny thing about Kemp is that when he went back to LA in 2018, He looked like his vintage 2011 self.

[@josidfin]

Another banger to watch 🔥

[@BaseballsNotDead]

Thanks!

[@isaiahlrice]

Most Reds fans knew that the Homer Bailey deal was awful. I realize what that Reddit thread said, but we knew. Bob Castellini saw 2 no-hitters and threw money at him.

[@albertosantana0423]

Best intro ever

[@kushclarkkent6669]

Poor Justin Morneau😔 The most Canadian looking player I've ever seen besides Jason Bay. RIP to both!

[@dirtface5923]

man poor Rickie weeks loved the guy as a brewer fan he worked hard as hell just couldn't put it all together still had a relatively fruitful career did some good and some bad stuff.

[@heyfling]

Ricky Romero must have just missed the cut $28m contract but he forgot how to pitch after signing it. Hitters started laying off his curve and his circle change, both of which he had a hard time throwing in the zone, and his fastball wasn't good enough to get a lot of swing and miss.

[@BaseballsNotDead]

Romero came in at -$17.6 million. There was only one free agent deal in the extension, so the damage was limited.

[@lsuperior]

Ron davis was my club coach for a couple years and that man is the single most hilarious person on the planet. He also saved a dozen people in a burning apartment during his playing days which you would never guess if you knew him. Too bad ike’s career was cut short by valley fever his son was great for a few years.

[@jrodddtv2373]

woah woah woah, Kemp came back to LA and had an All-Star season. Don't forget to mention that!

[@mmonkeyman1403]

The main thing I remember about Dontrel Willis was that I didn’t like how he wore his hat

[@saulspeaks2557]

The best baseball youtuber is back!

[@BaseballsNotDead]

The best baseball youtube commenter is back!

[@saulspeaks2557]

@@BaseballsNotDead you used my comments to make fun of me on another name and video, but I still tend to agree with your current assessment 😂

[@leollamel5886]

Those 2003 marlins had a crazy roster

[@myworms]

Matt Kemp made generational money for one awesome year of baseball.

[@TheSlurpeeMan]

Fun thing about Dan Petry being on this list: Detroit hockey fans can complain about his son's contract with the Red Wings now too!

[@Heathcoatman]

Bobby Bonilla may not make the list based on your criteria, but his deals with the Mets and Orioles, where his salary was deferred and he was getting paid over a mil per year after he retired. His Mets deferment was meant to go until 2035, though I'm not sure if it's still in effect.

[@BaseballsNotDead]

You're mixing up deals. Bonilla signed a free agent deal with the Mets and was traded to the Orioles partway through that, but none of that contract was deferred. He then signed a free agent deal with the Marlins, was traded to the Mets, and the Mets deferred the last year of THAT deal.

[@Heathcoatman]

@@BaseballsNotDead Well, I just oversimplified. Here's the Mets' deferment "After his subpar 1999 season, the Mets released Bonilla, but still owed him $5.9 million. Bonilla and his agent offered the Mets a deal: Bonilla would defer payment for a decade, and the Mets would pay him an annual paycheck of just over $1.19 million on July 1, starting in 2011 and ending in 2035, adding up to a total payout of $29.8 million". And then the thing with the Orioles "Bonilla also has a second deferred-contract plan with the Mets and Baltimore Orioles that was initiated in 2004 and pays him $500,000 a year for 25 years" You're right, I didnt nail down the deets, but I think it's an interesting situation that should slide in to one of these videos, if it already hasnt.

[@judychurley6623]

Preller and the Padres say "Hold my beer."

[@user-kq4hf8se5b]

Every time i see Bautista throwing the bat down in your opener. I think about the look on his face when he ran up on the pitcher and got punched in the face.

[@fortynights1513]

What is the name of the track you use in your intro?

[@BaseballsNotDead]

It's "Baseball's Not Dead Intro" (I recorded it) but it is based heavily off of Labyrinth by Miracle Musical.

[@KirbysFakePunt]

We asked and he delivered!!

[@dgrblue4162]

I have heard stories about concussions and how some can have many and still function and some can have one or two and it's like they have to relearn how to be themselves

[@joshuapatrick682]

How did Dye lose the MVP to Morneau in 2006? how did he lose it to 3 others besides? Dude smoked em...

[@doomnarok]

Aaron Hicks also guaranteed a 30/30 season. Dude has 71 career steals in 12 seasons

[@CoreyBlase]

The Carlos Martinez one hurts. He was supposed to be baby Pedro

[@gravitykat714]

True shame about Matt Harrison. Dude became the rangers ace after years of being number 4-5 and his back gave up on him.

[@Eazydoesit702]

Bro were you the voiceover for Supersize Me?

[@shoeless1137]

The Carlos Baerga segment says “Carlos Beltran” on the segment notes

[@danielpenrodii2389]

@12:10 yes, us “Twims frans” are having a negative reaction.

[@masonallen728]

You should do a video similar to your one ranking baseball movies on one called the hill Ok, movie baseball scenes are pretty decent, but I think it would be fun watching you tear it to shreds.

[@varianschirmer9375]

I'm surprised about this list. I had no idea about the size of overpayment on Lansing & Bailey. Especially from 2 organizations that are usually trade deadline sellers. I'm surprised Alex Rodriguez's re-up with NYY didn't slot in here. Given his 2nd 10-year-deal [after the opt-out] was basically financially trash after year 6. Two subpar seasons sandwiched around the year-long suspension and released with a year left. How much of that $300 million was wasted $$$... I also take the Aaron Hicks contract as documentation that the Yankees learned absolutely nothing from the Jacoby Ellsbury contract. Paying someone big $$$ for 5+ years because of 1 above-average full season.

[@BaseballsNotDead]

"I'm surprised Alex Rodriguez's re-up with NYY didn't slot in here." That's a free agent extension, not an arbitration extension.

[@varianschirmer9375]

@@BaseballsNotDead Fair enough.

[@theman1412]

Preston Wilson and Vinny Castilla really benefited playing in Colorado

[@jimmymcfarland4184]

As a Reds fan Homer was a bum from the jump! Should have traded him instead of Cueto. That deal set the Reds back for years. Thanks Walt Jocketty

[@trealville23]

The Reddit receipts are fucking hilarious 😂

[@chadcushing1638]

The goat !! Best videos

[@SpencerSpins]

I didn’t know Daniel Tosh had a baseball KZbin channel

[@santumi2298]

THIS IS LEGIT JUST THE AL CENTRAL LOL

[@Bruhsue]

As a dodgers fan, I still love matt kemp.

[@TheTylamo]

I thought Dan Uggla was Austin Riley for a second 😂

[@tylerrobinson6158]

I believe when d train switched his pitching stance thats what took a lot out of him

[@pathutchison7688]

Not so bad to only get one mention in “Moneyball”, considering Tim Hudson, Mark Mulder, Barry Zito and Miguel Tejada weren’t mentioned once.

[@travisp5747]

That movie portrays it as some dumpster fire of a team they’re working with. Honestly it kinda ruins it for me. I get it’s about the analytics but pitching analytics exists too

[@pathutchison7688]

@@travisp5747 plus having the AL MVP doesn’t hurt. But yea, it was all Scott Hatteburg.

[@nathanreynolds6459]

I think Paul DeJong's 6 year/$26M extension belonged on the list too

[@BaseballsNotDead]

Came in at -$22.6 million. It only bought out 1 free agent year, and he was Super 2 eligible, which limited the damage.

[@Crash33333a]

You ask how a pitcher could be better in their later years, well recovering from alcohol is 1 but anther huge reason is they realize they have no control when trying to throw to hard. Look at Greg Maddux, early in his career he was throwing in the low 90's hitting mid sometimes. What happened was he couldn't control where they went and when you get behind in the count, as a pitcher you have to toss it dead center and watch it fly. He learned to stop listening to the Cubs and worry more about control. He pitched in Venezuela for an off season working on just that, stop trying to throw hard and look where he wound up. There are plenty of pitchers who wound up doing the same but not the same results but still had really good careers. Even today a team will pay a pitcher who simply throws hard more money than a control guy believing they can teach him control. Same goes for batters, the power hitters get more money than contact hitters who strike out much less and drive in those late inning runs while the power guys are striking out trying to hit the HR every at-bat. Who do I want up in the bottom of the 9th with the winning run on 2nd, Edgar Martinez or Frank Thomas? Edgar every single game and he come thru at least twice as much as Thomas.

[@jimmyplenderleith9471]

How do you buy out "two free agent years"? Arent you a free agent after a year finishes, then you sign another contract....wouldnt that be one year? Hoping someone can explain?

[@BaseballsNotDead]

If a player has 1 year of team control left and signs a 3 year extension, that buys out two free agent years.

[@jimmyplenderleith9471]

@@BaseballsNotDead Ahh, OK....that makes sense...thanks for the explanation.

[@tucker4pf]

the two prospects the reds threw in with homer bailey were jeter downs and josiah gray, i hate being a reds fan so much

[@lukeyarasheski5510]

Was Bonillas' original contract an extension? Before they deferred it?

[@BaseballsNotDead]

It wasn't, but it wouldn't be close to this list regardless. His first free agent contract with the Mets actually fared OK. It was his second free agent contract with the Marlins where he was eventually traded to the Mets where the last year was deferred. Even with the deferrals, it's nowhere even close to as bad as people make it out to be. All of his deferrals combined is similar to what Stephen Strasburg will make just next year. Accounting for baseball revenue inflation, the deferral might have actually saved the Mets money versus just paying the $5.9 million in 1999. Plus it freed up that $5.9 million so they could acquire Mike Hampton, who was instrumental in the Mets making the 2000 World Series. I even have in the back of my mind to do a video in the future titled "Bobby Bonilla's Deferred Contract was Not That Bad." If you want to look at a bad deferred contract, Bruce Sutter's with the Braves was objectively WAY worse.

[@lukeyarasheski5510]

@BaseballsNotDead I just meant from a dead money stand point. I couldn't remember it was so long ago if it was a free agent deal or not

[@carlpacquing2575]

Man, I completely forgot about Carlos Martinez.