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Pesky Talk

Pesky Talk

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Every Worst Contract In MLB History Explained

Video Overview & Insights

Stephen Strasburg’s 7-year, $245 million deal with the Nationals post-2019 World Series saw him pitch only 26.1 innings over three seasons due to chronic nerve damage, retiring with a -0.5 WAR. Chris Davis’s 7-year, $161 million contract with the Orioles followed a stellar 2015 but led to a catastrophic decline, including a record 0-54 stretch and a -2.8 WAR, marked by a 37% strikeout rate. Anthony Rendon’s identical $245 million Nationals deal yielded a 3.9 WAR but was marred by injuries, apathy, and off-field issues, rendering him a league-average hitter. Kris Bryant’s 7-year, $182 million Rockies contract resulted in just 162 games over four seasons due to a litany of injuries, posting a -1.6 WAR. Albert Pujols’s 10-year, $240 million Angels deal, despite a 12.6 WAR, ended with a DFA and a -1.6 WAR in his final five years. Josh Hamilton’s 5-year, $125 million Angels contract was cut short. Xander Bogaerts’s 11-year, $280 million Padres deal started strong but saw his performance wane, with a 5.7 WAR and declining power. Jordan Zimmermann’s 5-year, $110 million Tigers contract produced a 1.9 WAR with a 5.63 ERA, far below his prior form. Madison Bumgarner’s 5-year, $85 million Diamondbacks deal ended with a DFA after a -0.4 WAR and a 6.5 ERA peak. Pablo Sandoval’s 5-year, $95 million Red Sox stint yielded a -1.6 WAR, cut short by injuries and weight issues. Jacoby Ellsbury’s 7-year, $153 million Yankees deal, despite a 9.6 WAR, was curtailed by injuries, missing three seasons. Finally, Eric Hosmer’s 8-year, $144 million Padres contract resulted in a 4.0 WAR, with declining performance and a trade after five years. These contracts, totaling over $1.9 billion, underscore the risks of long-term deals with players prone to injury, regression, or off-field issues, often leaving teams with minimal return on investment.

Finally Rendons Final year😭

— @MarcoBowker

Thumbnail Inspiration: @KaiTheBaseballKid @ThePaintExplainer

Bogaerts had a 4.2 ERA!?!?! Oh no!

— @demesisx

More User Perspectives

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10 year contract at 32 is crazy

@AntonioMorallis-c4y
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if a player sign’s a contract and wants an opt out,the owner should also have that opt out option also

@daveleegarner7267
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Angels signed all these players that failed and let go of Ohtani.

@anthonyf8937
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catchers get paid more for injuries so i can see why some cathers get more money then other fieldiers

@thepizzashopgaming
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Jayson Heyward…

@cdm27
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I’m sure Hamiltons relapse had to do with him tossing a ball into the crowd and having a father fall to his death in front of his son….

@cdm27
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If Aaron Judge would have gone to the Padres for $400 million+, they woudln't have wasted it on Bogaerts and would have made a WS run in 2023 and 2024.

@SteveDave211
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It's Ryan Howard for me the dude could only Hit one pitch to one spot a giant hole the biggest I ever seen from a pro and once he got hurt (before the contract too) they used a defensive switch and he couldn't Hit away from it and lost power to Hit above it,, it cost us maybe two World series. Definitely beaten SF and maybe Yankees we had the greatest top 4 starters ever

@VahMugga
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What is a lumbar 🫩✌️

@C4REFUL_KNF101
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Maybe not worst ever, but the Anthony Santander contract is looking to be pretty bad. 5 yrs/92.5m and he's so far finished year 1 with a -1.0 WAR, .175/.271/.294 and is already looking to be a non-factor on the Jays going forward.

@ImTheBowser
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Interesting, every player on this list (except Chris Davis) has a connection to at least one of 5 teams: Nationals, Angels, Red Sox, Padres, Giants.

Strasburg - Nationals
Chris Davis - none (but.... drafted by the Angels in 2005, didn't sign)
Anthony Rendon - Nationals, Angels
Kris Bryant - Giants
Albert Pujols - Angels
Josh Hamilton - Angels
Xander Bogaerts - Red Sox, Padres
Jordan Zimmerman - Nationals
Bumgarner - Giants
Pablo Sandoval - Giants, Red Sox
Jacoby Ellsbury - Red Sox
Eric Hosmer - Padres

@thorrfgump
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How did Xander Bogaerts post a 4.20 era? What am I missing here?

@P320
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Anyone remember Bobby Bonilla? The Mets are still paying for him.

@JabberCT
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Paying outrageous amounts to some of these and I won't watch it .They change the rules and it isn't baseball anymore. Haven't watched a game for years.

@bobjames3748
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The issue with Albert Pujols was that he was probably 3-4 years older than his stated age. Thereby already past his prime when he signed that contract.

@patrickloftus7336
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Kris Bryant still killing us in Colorado. Nice guy, I guess, but he really needs to hang up the cleats. Not that it matters much with the season we're having. It's almost better having him on the IL.

@brandonreimers7926
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The thing about Strasburg is he was babied from day one with his innings and starts and look how that idea turned out.

@ricogomez4020
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Nobody hasn't had a worst contract than Kris Bryant, I haven't seen or heard of dude since pre covid

@HotSauceInHerRose
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I feel like these players see the checks and feel like they don’t even need to try anymore

@rp3569
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WHY THE PLAYERS UNION and PLAYERS ASSOCIATION NEVER SAY ANYTHING ABOUT THIS

@camionerosfurgoneros5915
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Here is why we need to be engaged in the real spiritual battle.
1. Christ warns his early followers to “endure”, 22 And you will be hated by all for My name’s sake. But he who endures to the end will be saved. Matthew 10:22 (NKJV) This warning was given to his original apostles in preparation for the missionary work they will undergo.
2. The “endure” warnings have deeper meanings that should also be applicable to all humans. Here are the verses that clarify what Jesus meant. 12 For we do not wrestle against flesh and blood, but against principalities, against powers, against the rulers of the darkness of this age, against spiritual hosts of wickedness in the heavenly places. Ephesians 6:12 (NKJV) 8 Be sober, be vigilant; because your adversary the devil walks about like a roaring lion, seeking whom he may devour. 1 Peter 5:8 (NKJV) We are up against some are powerful beings that want to scalp our heads, that aim at targets on our backs.
3. These powerful oppositions are not to be underestimated. They are intelligent, they know exactly what they are supposed to do. They want us to rebel against God, be separated from him. Truly, this only I have found: That God made man upright but they have sought out many schemes.” Ecclesiastes 7:29 (NKJV) 13 And the Lord God said to the woman, “What is this you have done?” The woman said, “The serpent deceived me, and I ate.” Genesis 3:13 (NKJV)
4. They work hard to accomplish their objective. They don’t care what the collateral damage is as long as they make a believer turn his back to God. 12 And the Lord said to Satan, “Behold, all that he has is in your power; only do not lay a hand on his person.” So Satan went out from the presence of the Lord. 13 Now there was a day when his sons and daughters were eating and drinking wine in their oldest brother’s house; 14 and a messenger came to Job and said, “The oxen were plowing and the donkeys feeding beside them, 15 when the Sabeans raided them and took them away, indeed they have killed the servants with the edge of the sword; and I alone have escaped to tell you!” 18 While he was still speaking, another also came and said, “Your sons and daughters were eating and drinking wine in their oldest brother’s house, 19 and suddenly a great wind came from across the wilderness and struck the four corners of the house, and it fell on the young people, and they are dead; and I alone have escaped to tell you!” Job 1:12-19 (NKJV)
5. Going up against the devil is resisting him. It is not ignoring nor dismissing him. We should fight against him, do everything in our power to make him fail in accomplishing his objectives: so that no advantage would be taken of us by Satan, for we are not ignorant of his schemes. 2 Corinthians 2:11 (New American Standard Bible) 13 Therefore take up the whole armor of God, that you may be able to withstand in the evil day, and having done all, to stand. Ephesians 6:13 (NKJV) 7 Therefore submit to God. Resist the devil and he will flee from you. James 4:7 (NKJV)
Remember the original warning? The endurance is correlated with missionary work. The apostles were prepared to face adversities because they were to initiate ways to increase believers in Christ. That is what the enemies want to prevent. They will try their best to make each and every one of us join their rebellion against God. Stay within God's side, fight the Satan's schemes, and make him and his devils stop converting you into becoming rebels against God. That's pretty clear what the "endurance" mean. It is why we need to go to war against the enemy.

@StarsandSandGrains
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To this day, I will never forgive B.J. Upton for playing like some dogshit after signing that 5-year/$75 million deal. My Braves had to trade the GOAT closer in Craig Kimbrel just to get Upton's contract off the books! It's forever f**k that bum!

@ProfessorDarkness88
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You lead off with the two worst of all time and it's not even close. Stratsburg and Rendon are 1 and 1A. Both top 20 biggest contracts in baseball history.

@eamonkelley3811
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Have a good season before your contract is up and you'll make more money than most CEOs ever will.

@QuakerDragon
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Xander Boegarts aged badly, but it’s still a shit contract

@D4xnny
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Look at Pujols' first 8 years HR and RBI with the Angels - 2012 thru 2019.
30 - 105 in 154 games
17 - 64 in 99 games (close to a 30 100 full season)
28 - 105 in 159 games
40 - 95 in 157 games
31 - 119 in 152 games
23 - 101 in 149 games
19 - 64 in 117 games
23 - 93 in 131 games
That works out to 211 HR and 746 RBI over 8 years.
I defy you to find 3 First Basemen with better production over that same period. Not Votto, not Rizzo, who? Maybe Goldschmidt, Freeman and Cabrera. Maybe.

@rlsfrny
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Jason Bay!!!!!!!!!
Worst contract ever!!!!!!
Typical Mets!!

@kazitude1
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Bogearts is having a phenomenal 2025 season tho

@deathblock901
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Xander Bogaerts is too early to put in this “worst contract in MLB history” tier he had a bad first year but he’s been back to being xander ever since

@topicbaseball
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I’ll always remember him with a baseball size chawl in his mouth and a stupid look on his face

@GinaMcGraw-t2k
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Strasburg was such a talented pitcher, but he suffered from the stress he put on his shoulder/arm. He would’ve benefited if he converted to a reliever earlier similar to Aroldis Chapmen

@TheFlameofAnor
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Now do Giancarlo Stanton

@joes622
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Joe Mauer- mn twins

@domsWhad
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Pujols would have passed every record if he stayed solid but his fall off is so sad. Still my all time favorite player next to ICHIRO ❤️

@UnboxingYeti
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Why do they pay a 30+ year old player like they are in their low 20's

@darrenmashl5706
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Are these AI videos?

@Chelivgor
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Angels offer a good contract challenge impossible.

@ShawnSlaterEN
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BJ Upton signing with the braves. 5 years/75 million. (2013) His First season he batted .184. (2014) He batted .208 and was traded away in his 3rd season.

@leeroytravis6033
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if they sign me to a mlb contract i can break that 0-54 record

@hasbrosbeforehoes
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Teams in all sports over value players with championships. It happens in basketball football baseball im sure it happens in hockey even though the players in the NHL get shit for pay by comparison

@adambrunt7290
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"WAR" is a junk stat.

@Based_Proletariat
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You could just have bad Angels contracts in this video, and it would be longer than The Lord of the Rings.

@luckyjosh7
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The White Sox avoided this list by simply being cheap. Good job. 🙄

@billiam247
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How does a franchise like Washington stay afloat paying 2 players a half a billion dollars in the same 7 year period? that is just two players and a half a billion is gone...that's horrible business. That is why the UFC pays their fighters like they're homeless.

@joshthemediocre7824
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At 61 years of age that's why Ive hated baseball for a while. It's a joke as in the real world if you don't do your job well you'd be fired not paid for years after

@corymcewen5943
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I think al pro cintracts should be at tge league minimums with incentives and bonuses paid gor top performers.

@davidleigh443
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Red Sox fans love to complain about how the team isn’t trying to keep talent. But we’ve already pawned off one imminent disaster of a contract to an NL West team in Bogaerts. Devers is probably next.

@hornetguy9063
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Carl Crawford deserves a honorable mention

@stephensandler