Largest contract extensions in MLB history

To avoid losing key players in free agency, teams may look to sign them to contract extensions before they get the chance to test the open market.

The Phillies did just that with ace pitcher Zack Wheeler, signing him to a three-year, $126 million extension through 2027. With his five-year, $118 million contract with Philadelphia set to expire at the end of the 2024 campaign, Wheeler would have been eligible for free agency next offseason. At $42 million annually, Wheeler's new deal carries the highest average annual value for an extension in MLB history.

While Wheeler's new deal has a massive annual salary, Mookie Betts¡¯ $365 million extension with the Dodgers is the largest signed by a player in terms of new guaranteed total money added on to a player¡¯s existing contract.

Here's a look at the largest contract extensions in Major League history, in descending order of total dollars. (For a list of the longest contracts -- including free agent deals -- click here.)

1) Mookie Betts, Dodgers -- 12 years, $365 million
Signed in 2020, runs through 2032
The Red Sox traded Betts and southpaw David Price to the Dodgers in a blockbuster trade following the 2019 season, in large part because many expected the former American League MVP to test the market following the 2020 campaign and challenge the recent free agency standards set by Bryce Harper and Manny Machado. But Los Angeles¡¯ front office was able to hammer out a massive extension right as the shortened 2020 season was set to begin, adding on to the record one-year, $27 million contract that Betts and the Red Sox agreed to in January 2020 in order to avoid arbitration.

Making sure Betts stayed a Dodger was a no-brainer decision at the time, and proved even more so once the games got underway. Betts placed runner-up in the 2020 NL MVP Award vote, and then helped lead L.A. to a long-awaited World Series championship with a string of plays with his bat, legs and glove during the postseason.

This browser does not support the video element.

2) Mike Trout, Angels -- 10 years, $360 million
Signed in 2019, runs through 2030
The Halos made sure the game¡¯s consensus best player -- and one off to an historic start to his sure-to-be Hall of Fame career -- remained in Orange County for the foreseeable future. This deal added on to the two years and $66.5 million that were still remaining on the contract Trout signed in 2014, thus making his new 12-year, $426.5 million deal the richest in North American professional sports history at the time. Trout immediately rewarded the Angels¡¯ faith in 2019 by bashing a career-high 45 home runs and winning his third career league MVP Award.

3) Manny Machado, Padres -- 11 years, $350 million
Signed in 2023, runs through 2033
Machado originally joined the Padres on a 10-year, $300 million contract in February 2019, at the time setting a record for the largest free-agent deal in MLB history (though it has since been exceeded by several other deals). The contract gave him the ability to opt out at the end of the 2023 season, and Machado told reporters during Spring Training that he planned to exercise his opt-out power to test the open market. However, it appears he¡¯ll be staying in a Padres uniform for years to come. The extension will begin in 2023, effectively replacing the six years left on his previous deal with a new 11-year contract running through 2033.

4) Francisco Lindor, Mets -- 10 years, $341 million
Signed in 2021, runs through 2031
Under new owner Steve Cohen, the Mets hinted that the 2020-21 offseason would be a big one in Queens, and they delivered, landing Lindor and right-hander Carlos Carrasco in a trade with Cleveland. Once that deal was done, speculation turned to whether the Mets would be able sign Lindor, a four-time All-Star and two-time Gold Glove Award winner, to a long-term extension. The two sides reached a deal on March 31, the eve of Opening Day. Lindor's 2021 salary of $22.3 million remained unchanged, and the extension -- the richest ever for a shortstop -- took effect in 2022.

This browser does not support the video element.

5) Fernando Tatis Jr., Padres -- 14 years, $340 million
Signed in 2021, runs through 2034
After a promising but abbreviated rookie year in 2019, Tatis consolidated his promise with an electric performance in the pandemic-shortened 2020 campaign, slashing .277/.366/.571 with 17 homers in 224 at-bats and placing fourth in the NL MVP Award vote. His play was a major reason why the Padres snapped a 14-year postseason drought, and then he thrived under the brighter lights by becoming the third-youngest player to hit multiple homers in a playoff game. While the Padres missed the playoffs in 2021, Tatis finished with an NL-leading 42 homers, plus 25 steals and a .975 OPS in 130 games. Tatis missed the 2022 season with a wrist injury, followed by a suspension for a banned substance, but he returned to post a 5.5-WAR season (per Baseball-Reference) in 2023, making a successful switch from shortstop to right field.

6) Rafael Devers, Red Sox -- 11 years, $331 million
Signed in 2023, runs through 2033
With Xander Bogaerts departing for the Padres in free agency after the 2022 season, the Red Sox put their attention on keeping their other superstar, Devers, in Boston for the long haul. A year before Devers would have reached free agency, the Red Sox reached an agreement with their two-time All-Star third baseman on the largest contract in franchise history. Devers' deal surpasses the seven-year, $217 million free-agent contract David Price signed with the Red Sox in 2016, and the seven-year, $154 million extension Adri¨¢n Gonz¨¢lez signed with them in 2011.

7) Giancarlo Stanton, Marlins -- 13 years, $325 million
Signed in 2014, runs through 2028
Baseball had not seen this type of contract -- both in terms of length and total value -- before Stanton put ink to paper following the 2014 season. But the hulking slugger is playing out the majority of this deal with the Yankees, and not the Marlins; Stanton logged the first three seasons of the contract with Miami before the club traded him to New York in December 2017, shortly after he won that year¡¯s NL MVP Award. Stanton didn't enact his opt-out clause after the 2020 season, choosing to stay in the Bronx after some injury-plagued seasons in pinstripes.

8) Miguel Cabrera, Tigers -- 8 years, $248 million
Signed in 2014, ran through 2023
History repeated itself a bit here, as Dave Dombrowski -- the same general manager who signed Miggy to an eight-year, $152.3 million extension shortly after acquiring Cabrera for the Tigers via a trade in 2007 -- made sure Cabrera would stay in Detroit with an even bigger eight-year extension. This extension added on to the remaining two years and $44 million from Cabrera¡¯s previous deal, and briefly positioned the slugger for the highest annual average value in history at $31 million. Cabrera certainly earned a massive extension as he was coming off back-to-back AL MVP awards (including a Triple Crown season in 2012), but injuries took their toll in the latter half of this deal and he retired at the end of the 2023 season. He's one of seven players to produce at least 3,000 hits and 500 home runs in their career.

9) Nolan Arenado, Rockies -- 7 years, $235 million
(One year, $15 million later added onto deal)

Signed in 2019, runs through 2027
Less than one month after Arenado agreed to a then-record one-year, $26 million contract with Colorado to avoid arbitration, he was able to hammer out an extension with the club, adding seven years and $235 million to his existing contract. When the Rockies traded Arenado to the Cardinals prior to 2021 in exchange for left-hander Austin Gomber and four Minor League players, St. Louis tacked another year for $15 million onto the end of the contract in exchange for Arenado agreeing to waive his no-trade clause. He also gained the ability to opt out of his deal after the 2022 season, although he later chose not to do so.

This browser does not support the video element.

10) Joey Votto, Reds -- 10 years, $225 million
Signed in 2012, ran through 2023
Votto won the 2010 NL MVP Award and the Reds signed a three-year deal after that season in order to avoid arbitration. But eventually, Cincinnati rewarded its superstar in grand fashion. Votto paced the Senior Circuit in his specialty, on-base percentage, five more times after signing this extension and nearly won another NL MVP in 2017, finishing second to Stanton. After a pair of injury-plagued seasons, Votto became a free agent when the Reds declined his $20 million club option for 2024.

11) Clayton Kershaw, Dodgers -- 7 years, $215 million
Signed in 2014, signed additional extension in 2018
The reasons to give Kershaw a massive extension didn¡¯t require too much analysis. The southpaw had already captured two NL Cy Young Awards through his age-25 season and finished runner-up in another campaign, and he had lowered his career ERA in each successive season since making his debut -- a trend that would continue all the way through 2017. The Dodgers looked really smart immediately after Kershaw signed in January 2014, as he went on to win both his third Cy Young and the NL MVP Award after going 21-3 with a 1.77 ERA and 239 strikeouts. He and L.A. finally captured their long-awaited World Series championship in 2020.

This browser does not support the video element.

12) Derek Jeter, Yankees -- 10 years, $189 million
Signed in 2001, ran through 2010
This was the culmination of a prolonged negotiation process between Jeter and the Yankees that spanned 13 months. At the time, it trailed only the $252 million contract that Alex Rodriguez -- Jeter¡¯s future teammate -- signed with the Rangers in terms of the richest contract in baseball history. After signing in February, Jeter helped lead the Yankees to their fourth straight World Series appearance (earning his Mr. November moniker that fall) and continued his run as one of the most beloved players in Yankees history for the rest of the decade and beyond. He was elected to the Hall of Fame with 99.7% of the Baseball Writers' Association of America vote in 2020.

More from MLB.com

seductrice.net
universo-virtual.com
buytrendz.net
thisforall.net
benchpressgains.com
qthzb.com
mindhunter9.com
dwjqp1.com
secure-signup.net
ahaayy.com
tressesindia.com
puresybian.com
krpano-chs.com
cre8workshop.com
hdkino.org
peixun021.com
qz786.com
utahperformingartscenter.org
worldqrmconference.com
shangyuwh.com
eejssdfsdfdfjsd.com
playminecraftfreeonline.com
trekvietnamtour.com
your-business-articles.com
essaywritingservice10.com
hindusamaaj.com
joggingvideo.com
wandercoups.com
wormblaster.net
tongchengchuyange0004.com
internetknowing.com
breachurch.com
peachesnginburlesque.com
dataarchitectoo.com
clientfunnelformula.com
30pps.com
cherylroll.com
ks2252.com
prowp.net
webmanicura.com
sofietsshotel.com
facetorch.com
nylawyerreview.com
apapromotions.com
shareparelli.com
goeaglepointe.com
thegreenmanpubphuket.com
karotorossian.com
publicsensor.com
taiwandefence.com
epcsur.com
southstills.com
tvtv98.com
thewellington-hotel.com
bccaipiao.com
colectoresindustrialesgs.com
shenanddcg.com
capriartfilmfestival.com
replicabreitlingsale.com
thaiamarinnewtoncorner.com
gkmcww.com
mbnkbj.com
andrewbrennandesign.com
cod54.com
luobinzhang.com
faithfirst.net
zjyc28.com
tongchengjinyeyouyue0004.com
nhuan6.com
kftz5k.com
oldgardensflowers.com
lightupthefloor.com
bahamamamas-stjohns.com
ly2818.com
905onthebay.com
fonemenu.com
notanothermovie.com
ukrainehighclassescort.com
meincmagazine.com
av-5858.com
yallerdawg.com
donkeythemovie.com
corporatehospitalitygroup.com
boboyy88.com
miteinander-lernen.com
dannayconsulting.com
officialtomsshoesoutletstore.com
forsale-amoxil-amoxicillin.net
generictadalafil-canada.net
guitarlessonseastlondon.com
lesliesrestaurants.com
mattyno9.com
nri-homeloans.com
rtgvisas-qatar.com
salbutamolventolinonline.net
sportsinjuries.info
wedsna.com
rgkntk.com
bkkmarketplace.com
zxqcwx.com
breakupprogram.com
boxcardc.com
unblockyoutubeindonesia.com
fabulousbookmark.com
beat-the.com
guatemala-sailfishing-vacations-charters.com
magie-marketing.com
kingstonliteracy.com
guitaraffinity.com
eurelookinggoodapparel.com
howtolosecheekfat.net
marioncma.org
oliviadavismusic.com
shantelcampbellrealestate.com
shopleborn13.com
topindiafree.com
v-visitors.net
djjky.com
053hh.com
originbluei.com
baucishotel.com
33kkn.com
intrinsiqresearch.com
mariaescort-kiev.com
mymaguk.com
sponsored4u.com
crimsonclass.com
bataillenavale.com
searchtile.com
ze-stribrnych-struh.com
zenithalhype.com
modalpkv.com
bouisset-lafforgue.com
useupload.com
37r.net
autoankauf-muenster.com
bantinbongda.net
bilgius.com
brabustermagazine.com
indigrow.org
miicrosofts.net
mysmiletravel.com
selinasims.com
spellcubesapp.com
usa-faction.com
hypoallergenicdogsnames.com
dailyupdatez.com
foodphotographyreviews.com
cricutcom-setup.com
chprowebdesign.com
katyrealty-kanepa.com
tasramar.com
bilgipinari.org
four-am.com
indiarepublicday.com
inquick-enbooks.com
iracmpi.com
kakaschoenen.com
lsm99flash.com
nana1255.com
ngen-niagara.com
technwzs.com
virtualonlinecasino1345.com
wallpapertop.net
casino-natali.com
iprofit-internet.com
denochemexicana.com
eventhalfkg.com
medcon-taiwan.com
life-himawari.com
myriamshomes.com
nightmarevue.com
healthandfitnesslives.com
androidnews-jp.com
allstarsru.com
bestofthebuckeyestate.com
bestofthefirststate.com
bestwireless7.com
britsmile.com
declarationintermittent.com
findhereall.com
jingyou888.com
lsm99deal.com
lsm99galaxy.com
moozatech.com
nuagh.com
patliyo.com
philomenamagikz.net
rckouba.net
saturnunipessoallda.com
tallahasseefrolics.com
thematurehardcore.net
totalenvironment-inthatquietearth.com
velislavakaymakanova.com
vermontenergetic.com
kakakpintar.com
begorgeouslady.com
1800birks4u.com
2wheelstogo.com
6strip4you.com
bigdata-world.net
emailandco.net
gacapal.com
jharpost.com
krishnaastro.com
lsm99credit.com
mascalzonicampani.com
sitemapxml.org
thecityslums.net
topagh.com
flairnetwebdesign.com
rajasthancarservices.com
bangkaeair.com
beneventocoupon.com
noternet.org
oqtive.com
smilebrightrx.com
decollage-etiquette.com
1millionbestdownloads.com
7658.info
bidbass.com
devlopworldtech.com
digitalmarketingrajkot.com
fluginfo.net
naqlafshk.com
passion-decouverte.com
playsirius.com
spacceleratorintl.com
stikyballs.com
top10way.com
yokidsyogurt.com
zszyhl.com
16firthcrescent.com
abogadolaboralistamd.com
apk2wap.com
aromacremeria.com
banparacard.com
bosmanraws.com
businessproviderblog.com
caltonosa.com
calvaryrevivalchurch.org
chastenedsoulwithabrokenheart.com
cheminotsgardcevennes.com
cooksspot.com
cqxzpt.com
deesywig.com
deltacartoonmaps.com
despixelsetdeshommes.com
duocoracaobrasileiro.com
fareshopbd.com
goodpainspills.com
hemendekor.com
kobisitecdn.com
makaigoods.com
mgs1454.com
piccadillyresidences.com
radiolaondafresca.com
rubendorf.com
searchengineimprov.com
sellmyhrvahome.com
shugahouseessentials.com
sonihullquad.com
subtractkilos.com
valeriekelmansky.com
vipasdigitalmarketing.com
voolivrerj.com
zeelonggroup.com
1015southrockhill.com
10x10b.com
111-online-casinos.com
191cb.com
3665arpentunitd.com
aitesonics.com
bag-shokunin.com
brightotech.com
communication-digitale-services.com
covoakland.org
dariaprimapack.com
freefortniteaccountss.com
gatebizglobal.com
global1entertainmentnews.com
greatytene.com
hiroshiwakita.com
iktodaypk.com
jahatsakong.com
meadowbrookgolfgroup.com
newsbharati.net
platinumstudiosdesign.com
slotxogamesplay.com
strikestaruk.com
trucosdefortnite.com
ufabetrune.com
weddedtowhitmore.com
12940brycecanyonunitb.com
1311dietrichoaks.com
2monarchtraceunit303.com
601legendhill.com
850elaine.com
adieusolasomade.com
andora-ke.com
bestslotxogames.com
cannagomcallen.com
endlesslyhot.com
iestpjva.com
ouqprint.com
pwmaplefest.com
qtylmr.com
rb88betting.com
buscadogues.com
1007macfm.com
born-wild.com
growthinvests.com
promocode-casino.com
proyectogalgoargentina.com
wbthompson-art.com
whitemountainwheels.com
7thavehvl.com
developmethis.com
funkydogbowties.com
travelodgegrandjunction.com
gao-town.com
globalmarketsuite.com
blogshippo.com
hdbka.com
proboards67.com
outletonline-michaelkors.com
kalkis-research.com
thuthuatit.net
buckcash.com
hollistercanada.com
docterror.com
asadart.com
vmayke.org
erwincomputers.com
dirimart.org
okkii.com
loteriasdecehegin.com
mountanalog.com
healingtaobritain.com
ttxmonitor.com
nwordpress.com
11bolabonanza.com