Trout to Kiermaier: The richest signing of all 30 MLB teams

The Chicago White Sox just made Andrew Benintendi the richest player in franchise history. The South Siders signed Benintendi to a $75 million deal covering five seasons.

That got a lot of tongues wagging, and not about the amount or the fact that Benintendi was the target. The cause for the wagging: You mean the White Sox have never paid a player more than $75 million?

These days, when each week brings news of another MLB player signing up for well into nine figures, the idea that a franchise might never have paid out more than a mere $75 million for talent feels unlikely. That’s especially so considering that the White Sox play in a large market, and have been relatively successful.

They reached postseason play in both 2020 and 2021 before falling to an even .500 in 2022.

The fact is the White Sox are only one of five teams that have never signed a $100 million player. More strikingly, two of those five teams have played in the World Series within the past decade.

Who says you have to write the richest contracts to succeed?

Of course while money has been a deal in baseball for decades, it has become increasingly so in recent years. Of the 30 players who qualify as richest in the history of each franchise, 17 will take the field for that same franchise in 2023.

Five others were traded away when the signing franchise realized it could not afford its own richest player.

A look at the richest signing in every MLB team’s history

Make no mistake, money is flowing fast. Remember the famous Babe Ruth line? When quizzed about his $80,000 salary in 1930 being more than President Hoover, Ruth responded, “I had a better year than he did.” Adjusted for inflation, the $80,000 Ruth made in 1930 would amount to just $1.27 million today.

That’s about half what Tony Kemp is expected to make splitting time at second base for baseball’s cheapest team, the Oakland A’s.

From most to least expensive, here’s a look at each team’s richest signing in history. Although the list is ordered based on the raw dollar value of the deal, we’ve also noted each team’s largest average annual value, which is not always the same player.

1. Los Angeles Angels

The Angels made Mike Trout the game’s richest player when they signed him to a 12-year, $426.5 million extension prior to the 2019 season. The contract runs through 2030, and will pay Trout $37.117 million in 2023.

At an average of $35.5 million per season for the duration of the contract, Trout also leads the Angels when recalculated for average annual value. That AAV, however, has now fallen to third in the game with recent signings that exceed it.

Angels owner Arturo Moreno has always been accommodating when it comes to spending on talent, sometimes recklessly so.

Shortly after purchasing the team about 20 years ago, Moreno made Vlad Guerrero the second richest player in franchise history, signing him away from the Montreal Expos for $70 million over five years. (Mo Vaughn got $80 million over six seasons from the Autry family in 1998.)

When Torii Hunter signed on for five seasons at $90 million in 2008, he topped Vaughn’s franchise record. The Albert Pujols signing – 10 years, $240 million – set the record that Trout’s extension broke.

Moreno also famously signed Anthony Rendon in 2020 for $245 million spread across seven seasons,  the richest contract the Angels have ever handed to a player not already in their system.

The obvious irony is that neither the Rendon nor Pujols signings returned anything close to the value – in terms of on-field production – one might expect from that sort of payout.

2. Los Angeles Dodgers

The Dodgers acquired outfielder Mookie Betts from Boston in a February 2020 trade when the Red Sox despaired of signing Betts— a 2021 free agent-to-be — to an extension.

Then they turned around and did what the Sox would not or could not do, signing Betts to a long-term extension. The cost: $365 million over 12 seasons. The contract runs through 2032.

On a roster studded with multi-millionaires, the Betts contract does stand out, but not by all that much. In fact based on AAV, the richest Dodger in 2022 never took the field. That honor goes to suspended pitcher Trevor Bauer, who signed a three-year, $102 million deal (that’s a $34 million AAV) in 2021 then made only 17 appearances before being sidelined thanks to an allegation of domestic abuse. The status of Bauer’s contract is presently in front of an arbitrator.

With or without Bauer, Betts does not lack for country club company. Freddie Freeman last season signed a six-year, $162 million contract. A few years back the Dodgers picked up David Price and what was left of the seven year, $217 million deal he had signed with Boston, a deal that finally expired at the conclusion of this season.

For the approximately $48 million Price actually cost the Dodgers, they got amazingly little out of him; just a 7-2 record in 114 innings of work encompassing 11 starts and 68 relief appearances.

3. New York Yankees

Until recently, Gerrit Cole’s nine-year, $324 million contract signed prior to the 2020 season held the franchise record. Judge’s nine-year, $360 million deal blew that away, both for raw amount and AAV ($40 million).

The Yankees, of course, have a long history of featuring the richest players, going back to that Ruth contract in 1930. They ushered in the free agent era late in 1974, luring Catfish Hunter away from the Oakland A’s by ponying up the then-fantastic sum of $3.25 million over five seasons.

The current owner, Hal Steinbrenner, and his long-time owner father, George — often in concert with long-time general manager Brian Cashman — have over the years dispensed so much free agent cash that the following statement is true: Considering the 180 richest free agent contracts ever handed out in franchise history, not one was paid by an owner named something other than Steinbrenner, and only 14 percent were executed by a GM other than Cashman.

The most expensive of those 25 was a $25.5 million contract given by Gene Michael to Danny Tartabull three decades ago. It now ranks 28th richest on the franchise list.

From a pure dollar standpoint, the franchise’s glory days came more than a decade ago. In a span of 13 months in late 2008 and 2009,  the following occurred:

• George Steinbrenner resigned Alex Rodriguez to a 10-year, $275 million contract that was supposed to run from 2008 through 2017. Suspended in 2014, Rodriguez abandoned the final year of the deal and retired at the end of the 2016 season.
• Then Hal Steinbrenner resigned C.C. Sabathia to a seven-year, $161 million contract from 2009 to 2015.
• Finally, Hal signed Mark Teixeira to an eight-year, $180 million deal. In concert, those three signings played a large role in the winning of New York’s last World Series in 2009.

4. New York Mets

New Mets owner Steve Cohen made headlines with his avowed willingness to spend money on talent. He first lived up to his word by signing shortstop Francisco Lindor — acquired in a trade with Cleveland the previous winter — to an eye-catching 10-year, $341 million extension through 2031.

Then this week he hijacked Carlos Correa away from the Twins — by way of the Giants — for nine years and $315 million.

The Lindor deal is not only the richest in Mets history, it’s also the richest in terms of average annual value, ringing in at $34.1 million annually through the length of the contract.

That fact notwithstanding, Lindor projects to be only the third most expensive player on the 2023 Mets roster. Pitchers Justin Verlander and Max Scherzer were both signed this past winter to contracts (Scherzer for three years, Verlander for two) that will pay them $43.3 million in 2023.

Despite that, Lindor’s contract beats those two new additions in both raw money and average annual value.

Cohen’s impact could hardly be more visible. The Mets carried a team-record $159 million in 2019, the last pre-Covid season before Cohen took over. He raised that to $195 million in 2021, then to $264 million last year.

The 2023 projection had been to surpass $333 million, more than double what the team spent on talent just four seasons ago. With Correa’s signing, even that projection will have to be revised.

5. San Diego Padres

How aggressive is team president A.J. Preller? Of the nine most expensive outside free agents ever signed to a Padres contract, six (including the top three) were signed by Preller. There have been more misses than hits.

The player who put his name to the richest Padre contract, however, was not a free agent at all. He was and is suspended shortstop Fernando Tatis Jr. The Padres might like to forget it, but over the winter of 2020-21 they committed to Tatis to the tune of $340 million through 2034.

In a factoid that may qualify for Bizarroworld, it also means that a guy who appears to be a fifth wheel — they don’t need a shortstop and nobody’s sure he can play outfield — is the only player in baseball who knows exactly where he’ll be playing and for how much money in 2034.

The Padres’ commitment to their disgraced shortstop is so stretched out that it does not translate to the richest for average annual value. That distinction belongs to third baseman Manny Machado,  who signed a 10 year, $300 million contract prior to the start of the 2019 season. That works out to an even $30 million per season.

Preller has never managed to land a more expensive free agent than Tatis or Machado, but he’s come close. He famously made a late and unsuccessful run at Aaron Judge a few weeks ago. Prior to the start of the 2018 season, Preller locked up first baseman Eric Hosmer for seven seasons and $144 million. In 2015 pitcher James Shields signed for four seasons at $75 million.

Then there was pitcher Drew Pomeranz, four years, $34 million, in 2020. Jurickson Profar, three years, $21 million followed in 2021.

With the exception of Machado, every one of those signings looks questionable at best right now.

6. Philadelphia Phillies

A few days after the Padres signed Machado in 2019, the Phillies went them one better with the signing of free agent extraordinaire Bryce Harper. The deal was for 13 seasons (through 2031) and will bring Harper $330 million.

Harper’s deal set the Phillies’ record both for dollar amount and average annual value. The latter standard, however, was surpassed a few weeks ago when the Phils came to terms with free agent shortstop Trea Turner.

Turner’s 11-year, $300 million deal works out to a $27.3 AAV, comfortably above Harper’s $25.4 million AAV.

Owner John Middleton is the common thread to Philadelphia’s aggressive approach to player recruitment. The team’s 10 richest free agents in history were signed by five different GMs, but in eight of those signings the GM answered to Middleton. That includes not only Harper and Turner but Zack Wheeler, J.P. Realmuto, Nick Castellanos and Kyle Schwarber.

Middleton, you will recall, is the man who said the chase for Harper should not be slowed by debates over ‘stupid money.’

That gives the Phillies an imposing five players on their 2023 roster — Harper, Turner, Wheeler, Realmuto and Castellanos — who will draw in excess of $100 million before their Philadelphia contracts expire.

For comparison, the Yankees likely will have four such players, the Mets three and the Dodgers two.

7. Texas Rangers

With a $171 million projected 2023 payroll, the Rangers are not among the game’s runaway spenders. But new general manager Chris Young has shown that when he really wants somebody, he ponies up.

Just within the first two years of his tenure, Young has signed Marcus Semien for seven years at $175 million, Corey Seager for 10 years at $325 million, and (a few weeks ago) pitcher Jacob deGrom for five years at $185 million.

For raw value, Seager is the franchise’s all-time champ. Entering the second season of a deal that runs through 2031, he was a so-so player on a bad team last season. Apparently $325 million doesn’t go as far as it used to.

Because his contract is only half as lengthy as Seager’s, deGrom emerges the franchise’s new AAV champion. His deal works out to a hefty $37 million per year. Does that sound like a lot? It is; in fact on an AAV scale until Judge’s recent re-signing by the Yankees it was the richest deal in MLB history.

Put Seager, deGrom and Semien together and you have $94.5 million in AAV tied up in just three players through 2027. That’s on a team with an average payroll in the mid 130s since 2021.

If those three players don’t produce, the Rangers run the real risk of being financially hamstrung by their deals.

8. Miami Marlins

Yes, kids, there was a day when the Miami Marlins spent money. They did, however, live to regret it and vowed never to make that mistake again.

Prior to the start of the 2015 season, Marlins owner Jeffrey Loria actually shelled out $325 million over 13 seasons to get the signature of franchise star Giancarlo Stanton on a Miami contract. The deal was severely backloaded; Stanton received only $6.5 million in 2015 and didn’t hit $25 million until 2018.

The deal was also cynical. By the time Stanton did begin to collect the big portion of that contract in 2018, he had been marked for shipment out of town… as it turned out to the Yankees. They inherited the deal Loria had signed in a December 2017 trade.

Still, the Stanton contract is on the books as the richest ever signed by the Marlins both in terms of raw dollar value ($325 million) and AAV ($25 million per season through at least 2027).

Believe it or not, Stanton was actually the second plus-$100 million player signed by Loria. The first was free agent infielder Jose Reyes, who signed with Miami for $106 million spread over six seasons prior to the 2012 season.

That one didn’t work out for Miami, either.  Loria bore the cost just one season before including Reyes in a November 2012 12-player swap with Toronto. Reyes lasted just two seasons in Toronto before the Jays unloaded him to Colorado, setting off a hegira that also took him and the deal to the Mets and ultimately back to Colorado.

9. Colorado Rockies

Speaking of players who were signed and then dispatched…

Prior to the start of the 2019 season, the Monfort brothers — Rockies team owners — decided to make Nolan Arenado the face of the franchise. They accomplished that with an eight-year, $260 million contract through 2026 that the Rockies almost immediately regretted.

The contract so hamstrung Colorado’s maneuvering power with other players that in 2020 Arenado earned $35 million of a total $53 million team payroll, a jaw-dropping 66 percent of the whole payroll pie directed at one player.

Realizing the obvious payroll bind in which they had placed themselves, the Monforts prior to the 2021 season gift-wrapped Arenado to the St. Louis Cardinals. They did so at the price of a $51 million penance (the portion of the remaining $214 million the Rockies agreed to pay) for St. Louis to take Arenado’s contract off their hands.

In 2023, Arenado will make $35 million to play third base for the Cardinals. St. Louis will pay $19 million of that $35 million; the Rockies will pay the rest.

At $32.5 million per season, the Arenado contract is also the franchise’s  richest in terms of AAV Still, the Monforts haven’t entirely sworn off spending money. Over the winter of 2021-22, they gave the richest contract in franchise history to a player not already on their roster when they signed Kris Bryant for $182 million over seven seasons.

So far that one hasn’t worked out, either. Bryant spent most of his first season in Colorado on the injured list, getting in just 42 games.

10. Detroit Tigers

It was said of former team owner Mike Ilitch that he absolutely loved Miguel Cabrera. Well, there was a lot to love. Acquired from Miami in 2008, Cabrera has to date amassed more than 2,200 of his more than 3,000 hits and 369 of his 507 home runs in a Tigers uniform.

He was a core piece of Tiger playoff teams annually from 2011 through 2014.

For those reasons, Ilitch following the 2015 seasons locked up Cabrera for life, giving him an eight-year, $248 million contract. Considering that Cabrera was entering his age-33 season at the time, the deal was suis generis, and it has hamstrung Ilitch’s son and successor, Chris Ilitch, in his efforts to restore the Tigers to a relevant role in the AL Central.

In 2023, the final year of the deal, Cabrera will make $32 million, an amount that represents about 30 percent of the projected $110 million team payroll. It’s hard to build a team by committing 30 percent of payroll to one player, and harder still when that player is in his 40s.

The $248 million Cabrera contract is not only the richest in Detroit franchise history, at $31 million per season it’s also the richest in terms of AAV. The distant runners-up are the nine years and $214 million Mike Ilitch gave to Price Fielder in 2014 (a disaster of a deal for the Tigers, as it worked out) and the seven years, $180 million they gave Justin Verlander in  2013.

That Verlander deal aged better. He was the ace of the team’s postseason staff both in 2006 and from 2011. In time, though, the Cabrera signing crowded out the Verlander signing, and in 2017 the pitcher was off-loaded to Houston, where he helped the Astros to both the 2017 and 2022 World Series victories.

11. Washington Nationals

Of all the volatile assets in baseball, none is probably more routinely problematic than a very young, very talented pitcher.

As evidence of this, I give you Stephen Strasburg.

The Nats drafted Strasburg out of college in 2009, and welcomed him to the majors a year later. Arriving as a regular in 2012, he compiled 106 victories against just 54 losses between 2012 and 2019, and in 2019 was Most Valuable Player in the World Series, a series the Nats won in seven games over Houston.

The Nats celebrated that winter by re-upping Strasburg for seven seasons at $245 million, representing both the richest raw dollar amount ever paid by Washington and also — at $35 million per season — the richest AAV.

Strasburg was 30 at the time and with 1,450 innings on his arm, a league-leading 209 of them coming in the 2019 championship drive. (There were 36 more in the post-season run, but his total doesn’t count those.)

Then what seems to be the inevitable with brilliant young pitchers occurred to Strasburg … arm trouble. In the three seasons since signing that team record contract, he’s been on the mound for just 31 innings, or five fewer than he pitched in the 2019 post-season.

The net to the Nats has been one victory, four losses and a layout of $105 million minus whatever discount was applied for the Covid-shortened 2020 season.

If you ever wonder why GMs these days refuse to hand out long-term deals to free agent pitchers like they do to position players, the answer is Stephen Strasburg.

12. Seattle Mariners

Steal players from the deep-pocketed Yankees at your own peril.

The Mariners learned this lesson prior to the 2014 season when they made a successful run at free agent infielder Robinson Cano. To lure the long-time Yankee west, Seattle offered a franchise record $240 million across 10 years, through 2023.

It didn’t take long for the Mariners to regret their liberality. Cano hit well enough, averaging .296 with an .826 OPS. But he failed to lift the Mariners into postseason contention so, in December of 2018, they traded him to the Mets.

Suspended for all of the 2021 season for a PED violation, Cano puttered around with the Mets, Padres and Braves before being released.

Based on AAV, Cano’s deal does take a back seat in Mariners history. The richest in that category is pitcher Felix Hernandez, who prior to the 2013 season signed for $175 million over seven seasons. That works out to $25 million per season, about $1 million per season more than Cano’s 10 year, $240 million deal.

The Mariners got three good seasons and one decent one out of that seven-year Hernandez contract. Between 2013 and 2015 he was 45-25 with a 2.86 ERA in 642 innings. But from 2017 through 2019, he produced only a 15-27 record and a 5.42 ERA in just 314 innings.

13. Cincinnati Reds

Joey Votto is the face of the Cincinnati franchise. Way back in 2013, he signed a 10-year, $225 million extension that remains in force through this season’s end and remains relatively productive.

The Reds are not a rich franchise, a fact verified by the gap between what they pay Votto and what they’ve paid anybody else. A distant No. 2 on the all-time team payroll are Nick Castellanos and Mike Moustakas, who prior to the 2020 season both signed for identical four-year, $64 million deals.

That’s $159 million less and six years shorter than Votto. Then they lost Castellanos when he opted out after one year and signed instead with the Phillies.

Those are the only three players to have gotten Reds contracts in excess of $50 million. In terms of average annual value, Votto’s deal is also richest, at $22.5 million.

For 2023, Votto and Moustakas will combine to receive $43 million in salary, an amount that projects to be about 60 percent of the team’s total payroll. When 60 percent of payroll is devoted to two older players, that’s a recipe for disaster.

The question is  whether such a lopsided commitment to one player, even one of the level of Votto, has hamstrung the Reds. Since that deal was finalized in 2013, the Reds have had just one season with more than 83 victories and that was the first season, 2013. Since then, Cincinnati’s non-Covid season-long average win total under the Votto deal is an uninspired 69.6.

14. Boston Red Sox

The Red Sox are getting ripped for their refusal to spend. This winter they lost free agents Xander Bogaerts and J.D. Martinez, and negotiations with free agent-to-be Rafael Devers are said to be floundering.

A short time ago the team’s inability to agree to terms of an extension with Mookie Betts led them to trading their star right fielder.

Boston’s recent experience with long-term deals may have poisoned the team’s attitude. The team has since 2016 signed three players to headline-grabbing big-dollar contracts, and all three have thus far come up craps.

In fairness to the truth, two of those deals involved pitchers, a notoriously chancy group to commit to long-term. In 2016 the Sox gave a seven-year, $217 million deal to David Price, a franchise record both for dollar amount and AAV ($31 million.)

Price helped the Sox to the 2018 World Series title, but has done little since for either Boston or the Dodgers, to whom he was traded in 2020.

Then prior to the 2020 season they signed Chris Sale for $145 million over five seasons. A star since being obtained from the White Sox in 2016 who was also a major player in the 2018 World Series run, Sale almost immediately broke down.

Since signing the nine-figure contract, Sale is just 5-2 in only 11 starts.

The Sox’ third big deal, consummated last winter, sent $140 million Trevor Story’s way over six seasons through 2027. In 2022, Story delivered only a .238 average with an inglorious 102 OPS+.

15. Milwaukee Brewers

When the Brewers re-signed Yelich for $215 million through 2028, the presumption was they were getting a perennial contender for the batting title. The Most Valuable Player for Milwaukee in 2018 and runner-up in 2019, he had won batting titles both seasons, adding the slash line triple crown in 2019.

Both the $215 million raw figure and the resulting $23.9 million AAV are richest in franchise history.

It would take a batting coach, possibly working in tandem with a sport psychologist, to figure out what has gone wrong since. But Yelich’s offense has gone Hindenburg since 2019, plummeting 124 percentage points to .205 in 2025 and recovering since then only to the .250s.

Given the franchise’s small market status, it may not be surprising that Milwaukee’s love affair with Yelich is so much deeper from a dollar standpoint than its commitment, either current or historical, to any other player.

For the moment, second on Milwaukee’s list is recently departed center fielder Lorenzo Cain. Prior to the 2018 season, Cain signed a five-year, $80 million deal that just expired.

That’s $135 million less than the Brewers will have paid Yelich by the end of his contract. Not that the Brewers ever got full value from Cain, a part-time player at best after 2019.

That might change before Brandon Woodruff becomes free agent eligible in 2025. He has developed into the ace of Milwaukee’s staff. Assuming his health holds, they’ll have to either pay him big or watch somebody else pay him big.

16. Atlanta Braves

Identifying the richest-paid player in Braves history has been a fluid assignment in recent years.

When Ronald Acuña Jr. signed an eight-year, $100 million extension in 2019, he was that guy.

Acuña held the distinction through the angst surrounding the breakup with Freddie Freeman, but surrendered it to Freeman’s first base successor, Matt Olson. The Braves signed Olson for eight seasons at $168 million.

Then, a few weeks ago, Braves management rewrote the team’s payroll record book again, signing third baseman Austin Riley to a $22 million deal that will keep him in Atlanta through 2032.

At a $21.2 million AAV, Riley also holds that distinction.

The Braves show a consistent and decided preference for re-upping talent already in the system, a pattern that held true with Acuña, Riley, and Ozzie Albies (seven years, $35 million).

The obvious exception to that rule was Freeman, who walked away to the Dodgers after 2021, and getting $162 million over six seasons to do so.

They offset that loss by trading for and then signing Olson for eight years at $168 million,  and you can be the judge of who got the better of the Freeman-Olson “trade.”

17. Arizona Diamondbacks

D-Backs owner Ken Kendrick has never been one to let desert money flow freely. The largest team payroll in history is just $131.6 million. That’s modest by contemporary standards and that was back in  2018. Kendrick only spent $90 million on talent last year and isn’t projected to break $100 million in 2023 either.

The one time, really the only time, Kendrick let the D-Backs run financially wild was over the winter of 2015-16 when he decided that the way to make up ground on the division rival Dodgers was to heist one of their ace pitchers.

A $206.5 million promise to Zack Greinke, the National League’s reigning ERA champion, payable over six seasons, accomplished that.

It was then and remains today the richest single payout in franchise history, both for raw dollar expense and (at $34.4 million) at AAV.

In due course, Kendrick regretted that moment of madness. So when Greinke won 55 of 84 decisions for an Arizona team that was swept out of its only postseason appearance, Kendrick swapped the costly star to Houston at the 2019 trade deadline.

The Greinke deal was completely out of character for Arizona, whose next richest free agent award, to Madison Bumgarner, registered only $85 million over five seasons. That’s less than half what they paid for Greinke.

More in character was the December 2018 trade that dispatched team star but free agent-to-be Paul Goldschmidt to St. Louis. There he signed a $144.5 million, six year contract — far less than the cost of Greinke — that runs through 2024.

18. Minnesota Twins

Enough doom and gloom. Enough about players who were too costly to keep (Greinke, Stanton, Arenado), who got hurt (Strasburg) or who underperformed (Price, Yelich, Cano).

Time to celebrate an unqualified success.

Prior to the 2011 season, the Twins celebrated their relationship with catcher Joe Mauer by signing him to an eight-year, $184 million deal through 2018. Mauer moved to first base four seasons into the deal, but that isn’t the point.

The point is that both sides were actually happy.

Mauer made it a productive eight seasons for the team with which he spent his entire 15-season career. He topped .300 three times in those eight seasons, led the league in on base percentage once, and made the final two of his total of six All-Star teams.

At an average of $23 million per season, Mauer’s contract stood as the franchise richest for AAV until surpassed by Carlos Correa’s three-year, $105 million deal. That worked out to a $35 million AAV.

As previously noted, Correa then exercised his opt-out clause this winter and a few weeks ago signed a new and even more lucrative deal with the San Francisco Giants. When that fell apart, he signed instead  with the Mets for nine seasons at $315 million.

The Twins’ current richest in cash is Byron Buxton, who last year signed a seven-season, $100 million extension.

19. Chicago Cubs

The richest contract in Cubs franchise history went to a .245 hitter with a lifetime 86 OPS+ during his time with the team. But brother, could he deliver a speech.

In Chicago, it was Jason Heyward’s oratory — specifically the speech he delivered in the weight room at Cleveland’s Progressive Field while waiting out a rain delay prior to the 10th inning of Game 7 of the 2016 World Series — that made him famous.

His teammates credited Heyward with rallying the club after a Rajai Davis home run erased a Cub lead and appeared to put Cleveland on track to win the Series.

A player can contribute in many ways. Heyward may not have justified his eight-year, $184 million contract with his bat. But if his William Jennings Bryan weight room imitation did indeed set the Cubs on course for their first World Series win in 108 seasons, all is forgiven in Chicago.

For AAV, Heyward’s contract was surpassed by the six-year, $155 million contract the team gave his teammate, pitcher Jon Lester. That works out to $25.8 million per year. Lester didn’t hit either, famously couldn’t throw to a base and he didn’t talk much, but the guy could sure pitch.

He went 77-44 for the Cubs, including 19 victories in that 2016 World Series season and 18 more in 2018.

As for Heyward, the Cubs released him following the 2022 season, opting to eat the final $22 million. He has since signed a minor league deal with the Dodgers.

20. San Francisco Giants

Had this list been published a few days ago, the Giants would have ranked fourth. The reason: Their new signee, shortstop Carlos Correa, was on board for 12 years and $350 million.

Never mind.

For reasons still to be revealed, that deal got hung up and then scrapped due to some aspect of Correa’s physical. Literally by daybreak he had pivoted to the Mets for fewer years and fewer dollars.

It comes on the heels of San Francisco’s near miss in the signing competition for Aaron Judge. He spurned San Francisco to resign with the Yankees, also for nine years and $360 million.

That means the Giants’ richest signee today is actually still the same guy it was a week ago. That would be Buster Posey. In 2013 he signed a nine-year, $167 million extension.

It not only leaves Posey with the franchise’s all-time richest contract, it also leaves Carlos Rodon, and his two-year, $44 million deal ($22 million AAV) as the richest in that category.

Both of those would have been easily washed away by either the Correa or Judge signings, had either happened. In that event, the Giants would have ranked fourth or higher on this list.

But because both fell through, San Francisco plummets a full 16 places on this list, all the way down to 20th.

21. Houston Astros

Considering that they are the only team since 2015 to have won more than one World Series, it may surprise some to find the Astros this low on the list. What Houston has consistently proved is that solid player development — which leads to production during pre-arb and pre-free agency seasons — can be a marvelous tool for success.

The Astros have never signed an outside free agent for more than $100 million. They hit that figure once (with Carlos Lee on a six-year deal in 2007) and swore off the practice.

The present roster is dominated by pre-arb and early arb players buttressed by a few system products who have received significant but not bank-breaking extensions.

Number 1 on the latter list is second baseman Jose Altuve, who prior to 2018 signed a seven-year, $163.5 million deal. That works out to a $23.3 million AAV.

Literally the only other Astro who carried a nine-figure pricetag is Alex Bregman. He signed for $100 million over five seasons in 2020.

The Astros did have Zack Greinke for two seasons of his $206.5 million contract with Arizona. But the D-Backs paid $20.66 million of the $70 million Greinke was owed during those two years, reducing Houston’s cost to $49.33 million.

22. Baltimore Orioles

Oddly, two players named Chris Davis (okay, one is named Khris Davis) come up on this list.

The Orioles’ Chris Davis signed for seven years at $161 million prior to the 2016 season. The Orioles thought they had good reason to lock up Davis, a power hitting first baseman who had twice led the AL in homers.

But Davis was 30 when ink hit paper and, as it turned out, approaching a steep performance decline.

His home run total fell to 38 in 2016, then to 26, 16, 12 and a rock bottom of zero during the 2020 Covid short season. For the life of the contract, he never hit above .221 and only once produced an OPS+ above the league average of 100.

The 2020 season was the end for Davis, the Orioles eating the $46 million they owed him through 2022.

For the record, at a $23 million AAV, Davis also holds the franchise lead in that category. He may not hold the team record for long, though, given the potential for development shown by young stars Adley Rutschman, Cedric Mullins, John Means, Austin Hays and Ryan Mountcastle.

23. Toronto Blue Jays

The Jays have from time to time joined the chase for borderline top-tier free agent talent. But they don’t generally make a habit of it.

The three exceptions both involved sluggers who, by modern standards, came at a bargain.

The first was Vernon Wells, a re-up the Jays extended in 2008 at a cost of $126 million over seven seasons.

That remained the franchise record, although Toronto pushed it in 2014.  That’s when the Jays agreed to take on the six years and $118 million that remained on a deal the Rockies had signed one year earlier with their shortstop, Troy Tulowitzki. The Jays acted on the mistaken notion that, if you can hit in Denver, you can hit in Toronto.

A consistent .300 bat with power for the Rockies, Tulowitzki labored through parts of three injury-plagued seasons for the Jays before being released, at a cost estimated at close to $60 million.

By then, Jays management was ready to try a third time, and this time their target was Astros outfielder George Springer. They got him at what is today a franchise record of $150 million over six seasons through 2026. The $25 million AAV is likewise a franchise high.

Springer was the first of two nine-figure Jays signees, the second being Kevin Gausman. Prior to 2022 he signed a five-year, $110 million contract.

24. Cleveland Guardians

The Guardians — and in their previous iteration as the Indians — have never signed an outside free agent for more than $60 million. That’s what they gave Edwin Encarnacion in exchange for a three-year commitment prior to the 207 season.

Encarnacion gave the Indians two decent seasons and then was included in a three team, five player trade that shipped him to Seattle.

At $20 million per season, Encarnacion’s contract was also the Cleveland franchise record for AAV … until the spring of 2022, when the Guardians came to terms with their own star third baseman, Jose Ramirez. His seven year, $141 million deal more than doubles the Encarnacion deal for raw value, and the, and the $20.1 million AAV is also a franchise record, albeit barely

Ramirez will earn $14 million this year, that amount rising to $23 million by 2027.

How long the Ramirez contract will be the benchmark is another question. Star pitcher Shane Bieber and infielder Amed Rosario are both approaching free agent eligibility, and the pressure to keep them is likely to be strong.

The question is the element of payroll flexibility the Guardians do or do not have. The recent signing of free agent Josh Bell drove Cleveland’s 2023 payroll to a projected $89 million, which is far higher than the $51 million of the past three seasons but far lower than the $128 million average the team then known as the Indians spent on talent between 2017 and 2019.

If Guardians management is willing to spend at 2018 levels, then they can compete for Bieber and Rosario.

25. St. Louis Cardinals

The Cardinals have been such a perennially successful franchise that it is odd to consider that only five teams have paid their highest-paid player less than St. Louis.

Leadership in St. Louis has developed the art of vulturing other teams’ bad contracts. That’s how they got Nolan Arenado away from Colorado in February of 2021. That deal will pay Arenado $199 million to play for St. Louis, but he will cost the Cardinals only $148 million; the Rockies will pay the other $51 million.

They’d already effectively pirated Paul Goldschmidt from the Diamondbacks under similar circumstances. The D-Backs went looking for a suitor for Goldschmidt when he was a free agent candidate, and pawned him off on the Cardinals, who promptly resigned him for $130 million over five years.

For the record, that’s the Cardinal franchise record, surpassing the $120 million they had given to Matt Holliday after acquiring him from Oakland in yet another imminent free agency-related trade giveaway in 2009.

Go back far enough and the same can be said of the acquisition of Mark McGwire from Oakland back in 1997.

At an AAV of $26 million, Goldschmidt’s deal also sets the franchise record for that category.

26. Kansas City Royals

The Royals are viewed as a small market franchise, but they’ve had their moments. Between 2015 and 2018, they averaged a solidly middle class $127 million payroll, and along the way won a World Series.

That spending spree included giving $72 million over four years to Alex Gordon in 2012. That was the team record until 2022, when the franchise ponied up $82 million over four years for perennial All-Star catcher Salvador Perez, who was coming off a league-leading 48 home runs and 121 runs batted in.

That contract is off to a fairly tepid start. In 2022, Perez played just 114 games and hit a so-so .254 in its first season. His home run production fell to 23, his RBI total to 76.

The Perez contract dominates the current Royals’ landscape. It is likely to project to more than one-quarter of the total team payroll, and for the moment at least equates to nearly as much as the team’s next three highest paid players.

At a $20.5 million AAV, Perez’s deal now holds the Royals record in that category as well.

Both of those, of course, were in-house extensions. For an outsider, the biggest deal was a five-year, $70 million contract to starter/reliever Ian Kennedy in 2016.

27. Chicago White Sox

So we finally get to the White Sox, who started all this by signing Benintendi to that five-year, $75 million deal. What were the Sox spending their money on prior to this week?

Yasmani Grandal set the previous franchise record when he signed a four-year, $73 million contract prior to the 2023 season.

The $70 million level has been something of a capstone figure on the South Side. Before Grandal, that’s what Yoan Moncada signed for in 2020. In 2015, they signed Jose Abreu for $68 million over six years, and a fraction more than the $65 million paid to John Danks over five seasons beginning in 2012.

Back in 2009, Alex Rios got $64 million over six seasons. And from 2006 through 2009, Jim Thome played for Chicago under terms of an $80 million deal Thome had signed while he was playing for the Phillies.

In one sense, Paul Konerko is the champion earner on Chicago’s South Side. He pulled down more than $129 million over the course of his 16-season career with the Sox. But Konerko did that under a succession of separate deals, none of which exceeded the five year, $60 million deal he signed prior to the 2006 season.

28. Pittsburgh Pirates

The Pirates were at the bottom of this ranking until wedging their pockets open far enough this past spring to sign promising third baseman Ke’Bryan Hayes to an eight-year, $70 million extension.

The $70 million figure broke the franchise record previously set by the 2012 signing of Andrew McCutchen for six years at $51.5 million.

McCutchen made it through most of that contract before becoming a financial drag on the Pirates. So prior to the start of the 2018 season, the Pirates traded McCutchen and the option they still held on him to the Giants for a couple of prospects, one of whom developed into Bryan Reynolds.

The financial commitment to Hayes will be noteworthy if Pirates management can construct enough of a supporting cast to make it meaningful, and also if Hayes can produce at a higher level than his .244 average and 87 OPS+ of 2022. But he’s only 25 with plenty of room for growth, so hope remains in order.

Looking strictly at AAV, both the Hayes and McCutchen deals take a back seat to one given to pitcher Francisco Liriano. The Pirates resigned him prior to the 2015 season for three years at $39 million, a $13 million AAV.

Among franchise record AAVs, by the way, that’s the record low. Hayes’ only works out to about $8.75 million per year, McCutchen’s to about $8.58 million.

30. Tampa Bay Rays

Just two seasons ago, the Tampa Bay Rays played to Game 6 of the World Series. Since 2018, they have produced a winning record annually, and have a .590 winning percentage for that period.

How do they do it without spending any money?

Never in their 25-season history have the Rays given out a contract in excess of $53 million. That’s what Kevin Kiermaier agreed to play center field for from 2017 through 2022.

That deal having just expired, Kiermaier is a free agent and the Rays still aren’t going overboard. Their most recent headline signings include Zach Eflin, three years, $40 million, and Tyler Glasnow, two years, $30.35 million. Eflin’s deal is the largest ever given by Tampa Bay to a player not already in their organization

The team payroll may actually decline next season, from just under $84 million to below $70 million.

Even so, in Vegas plenty of smart guys still like Tampa Bay’s chances in the AL East.

Although Kiermaier is the franchise leader for total amount, Glasnow holds the record for AAV at $15.175 million.

The Rays can do this because they have the management skill to load up on young talent that generates far more in on-field value than it sucks up in salary.

Looking strictly at 2022 WAR, the five team leaders were Shane McClanahan, Jeff Springs, Yandy Diaz, Drew Rasmussen, and Randy Arozarena. As a group, they delivered 16.8 WAR at a total cost of less than $6 million, or about $1.2 million a head.

Maximum production at minimal expense is a wonderful formula for success both on the field and in the front office.