Ah, July 1st. Or as baseball diehards more commonly know it as: Bobby Bonilla Day. For baseball fans, perhaps no day on the baseball calendar induces more head scratches than July 1st. Brought to notoriety by the day’s namesake and his annual deferred payments of $1.19 million he’s received from the Mets from 2011 through 2035, Bobby Bonilla Day offers an opportunity to look at some of baseball’s most interesting contract language and maddening deals ever signed. From guys like Bruce Sutter and Bret Saberhagen getting paid well into their 60s to future albatross payments to players like Chris Davis and Ichiro Suzuki, many teams are set to be on the hook and paying guys decades after retiring. To properly celebrate Bobby Bonilla Day, let’s take a look at 15 of the biggest deferred money MLB contracts ever signed.

Biggest Deferred Payment Contracts in MLB History

Matt Holliday

Dollars and years: $15 million over 10 years

Years of deferred payments: 2020 – 2029

Who owes him: St. Louis Cardinals

Average annual salary per payment: $1.5 million

Age when payments stop: 49

An All-Star four times in his seven full seasons in St. Louis, Matt Holliday helped the Cardinals win two NL pennants plus a World Series in 2011. After trading for him in 2009, the Cards re-signed Holliday to a 7-year, $120 million deal in January of 2010, with $15 million of that being deferred. They got plenty of mileage out of him in his Cardinals tenure, but come 2020, July 1st will be Cardinals fans’ version of Bobby Bonilla Day.

Chris Sale

Dollars and years: $50 million over 5 years

Years of deferred payments: 2035 – 2039

Who owes him: Boston Red Sox

Average annual salary per payment: $10 million

Age when payments stop: 50

Chris Sale won’t start getting paid until he’s 46, but like every agent who put deferred money language into their clients’ deals, give those dudes a raise. As part of his 5-year, $145 million extension signed in March of 2019, Sale had $50 million of it deferred more than a decade and a half into the future. The seven-time All-Star and MLB’s all-time leader in K/BB and K/9 ratios was deemed a worthy investment for the Red Sox, and those $10 million annual checks Sale will get in his mid and late 40s should help make retirement a little easier for him to stomach.

Todd Helton

Dollars and years: $13.1 million over 10 years

Years of deferred payments: 2014 – 2023

Who owes him: Colorado Rockies

Average annual salary per payment: $1.31 million

Age when payments stop: 49

Presented with a two-year extension in 2010, the Rockies made the Toddfather an offer he couldn’t refuse. With $13.1 million in deferred payments as part of the language of his final big money MLB contract, Todd Helton started receiving annual payments of $1.31 million from the Rockies in 2014. Set to keep getting those yearly installments until he turns 49, the Rockies’ all-time leader in in homers, hits, runs and RBIs (among way too many other stat categories), the man who spent all 17 of his seasons with Colorado will keep being paid handsomely by his club 10 years after his retirement.

Bret Saberhagen

Dollars and years: $6.25 million over 25 years

Years of deferred payments: 2005 – 2029

Who owes him: New York Mets

Average annual salary per payment: $250,000

Age when payments stop: 64

Oh yeah, Bobby Bonilla isn’t the only guy who hasn’t played in like two decades who’s still on the Mets payroll deep into the next decade. A two-time Cy Young award winner by the time the Mets signed him ahead of his age-28 season in 1992, Saberhagen only won 10 games in his first two seasons as a Met. He’d be traded halfway through his fourth season and be largely considered a disappointment despite a top-3 Cy Young finish in 1994. Saberhagen’s deal paved the way for Bonilla’s more widely-known deal to be made (and ultimately create Bobby Bonilla Day). Saberhagen will keep getting paid by the Mets more than 35 years after his final full season with the club. DAMN YOU, BERNIE MADOFF.

Max Scherzer

Dollars and years: $105 million over 7 years

Years of deferred payments: 2022 – 2028

Who owes him: Washington Nationals

Average annual salary per payment: $15 million

Age when payments stop: 43

Deferring half of his 7-year, $210 million contract to 2022 through 2028, this may be the only deal that you can actually say isn’t hurting the team who signed him. Through his first four seasons in DC, Scherzer won a pair of Cy Young awards and led the NL in strikeouts three times (he’s on pace to do it a fourth straight year). Scherzer is as durable and filthy as they come, and hasn’t posted an ERA higher than 2.96 in any of his nearly five years as a Nat. Scherzer set himself up well when his contract runs out following the 2021 year at which point he’ll be 36 years old.

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Click to Page 2 to see what guys like Ken Griffey Jr. and Manny Ramirez are still owed.

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