What if Andrew McCutchen hadnt signed an extension with the Pirates?

Every Wednesday, The Athletic’s MLB writers will be looking at a key what-if scenario from baseball’s history. This week: Former MVP Andrew McCutchen and the Pittsburgh Pirates.

There was a time when the thought of Andrew McCutchen playing home games anywhere but PNC Park in Pittsburgh felt wrong; a time when McCutchen had made the Pirates winners again; a time when the team’s principal owner, Bob Nutting, and the face of the franchise spoke the same language and agreed that McCutchen should stay a “Pirate for life.”

The seed of that dream was planted when the Pirates picked McCutchen 11th overall in the 2005 draft. It crystalized seven years later on a cloudless day at the Pirates’ spring training ballpark in Bradenton, Fla., as the 25-year-old sat alongside Nutting and then-general manager Neal Huntington at a March 6, 2012, news conference announcing a contract extension: six years and $51.5 million guaranteed, plus a $14.75 million club option.

“We’re not signing a baseball player,” Nutting told reporters that day. “We’re signing a person we believe in greatly.”

Over the life of the contract, McCutchen would emerge as a baseball star, win an MVP and a Gold Glove, snap the Pirates’ streak of 20 consecutive losing seasons, return them three times to the playoffs, and then decline. The Pirates would fall fast, too, and ship out their five-time All-Star center fielder in 2018 to spend the last year of the deal playing for the Giants and Yankees.

But on that day in Bradenton, McCutchen saw only a bright future ahead. He stood, shook Nutting’s hand and smiled while camera shutters clicked.

“It’s almost like being married,” McCutchen said, “and you renew your vows.”

Now, the McCutchen contract extension is an interesting case study in which timing was, in fact, everything. Wait any longer and he might have played himself out of the Pirates’ price range. So, nine years later, consider this hypothetical: What if McCutchen had rejected the Pirates’ offer that spring? The impact — for him, for them — may be much larger than you realized.

The setup

The Pirates had been trying to extend McCutchen since he broke into the majors in 2009 and finished fourth in National League Rookie of the Year voting. McCutchen wanted to wait until he had played at least two full seasons before seriously considering signing an extension. He understood the risks involved but also knew the cost of locking up his prime years so early.

In 2012, McCutchen was ready to talk. He was coming off of his first All-Star season, with a .276/.365/.458/.822 career slash line. He had power, speed and patience at the plate. Baseball-Reference’s top player comparisons to McCutchen at that point: Reggie Smith, Ellis Burks, Bobby Bonds and Carlos Beltrán. Good company. The comps for a McCutchen contract extension were clear. Justin Upton and Jay Bruce — who went first and 12th, respectively, in McCutchen’s draft — had signed almost identical extensions that McCutchen and his agent, Steve Hammond, felt had set the market. Upton: six years, $51.25 million. Bruce: six years, $51 million and a $13 million club option. That, it seemed, was the going rate for pre-arbitration outfielders.

Offensive numbers through 2011

“That was the market for me at that time,” McCutchen told the Philadelphia Inquirer in 2019, “and that was the decision I made on my end. The market wasn’t getting higher.”

Not yet, anyway.

For McCutchen, a bigger payday …

By signing the extension, McCutchen delayed the date he’d hit free agency by three years. And in his case, the difference between 2015 McCutchen and 2018 McCutchen was immense.

Had McCutchen reached free agency in the 2015-16 offseason, after his age-28 season, he would have been the only premier center fielder — and perhaps the best position player — on the market.

See, immediately after the extension, McCutchen’s game soared to another stratosphere. Over the next four seasons, he batted .313/.404/.523/.926, averaging 25 homers, 90 RBIs, 19 steals and 6.5 WAR per year. In 2012, he won a Gold Glove. In 2013, he was the National League MVP. He added four All-Star appearances, four Silver Sluggers and three trips to the playoffs.

It’s that version of McCutchen who would have been a free agent.

Top free-agent position players in 2015

* ages listed are as of Nov. 1, 2015.

Four position players exited free agency that offseason with new contracts carrying an average annual value (AAV) greater than $20 million. McCutchen, whose extension had an AAV of $9.4 million when maxed out, had easily outpaced all four in WAR since 2012: McCutchen 26.2, Heyward 21.4, Céspedes 16, Davis 14.7, Upton 12.5. Free agents are paid for past production, and, well, McCutchen’s first seven seasons were a sight to behold. (His closest age-28 comp, according to Baseball-Reference, was Christian Yelich.) At the time, in 2015, while McCutchen’s stolen-base numbers and defensive metrics had started to slip, there was little reason to believe his bat would slow.

I ran this hypothetical past The Athletic’s Jim Bowden, a longtime former general manager, and asked what type of contract McCutchen might have gotten had he been a free agent in 2015. He thought it through. McCutchen was a year older than Upton and three older than Heyward, but better than both. Bowden came up with this: seven years and $171.5 million, a $24.5 million AAV. (When I polled some national writers about this in 2019, one guessed an even longer deal — nine years, $220 million, a $24.4 million AAV.)

It’s anyone’s guess which teams would have been in on McCutchen. The Cubs were big players that offseason, joining the Tigers, Giants, Red Sox, Orioles and Diamondbacks in spending more than $200 million on free agents.

As it played out, McCutchen’s production had tailed off by the time he reached free agency in 2018. It wasn’t a blip. He was newly 32, a corner outfielder with pop, but no longer one of the best in the game. He still signed a handsome contract with the Phillies, a three-year deal for $50 million guaranteed that will end this year unless Philadelphia exercises his $15 million option for 2022.

Add it all up, and McCutchen has made about $115 million in salary and bonuses in his big-league career. That’s no small sum. But between what he’d have gotten in arbitration and free agency in 2015, it’s likely McCutchen missed out on at least $85 million in career earnings by signing the extension.

For the Pirates, a bigger decision …

Had McCutchen rejected the extension in 2012, the Pirates would have had to choose one of three routes as McCutchen entered his prime:

Extend him later: Maybe Upton and Bruce had set the market for McCutchen, but by the end of the 2012 season, it would have been foolish to continue comparing them. That season, McCutchen led the league in hits, smashed 31 homers, drove in 96 runs, stole 20 bases and won a Gold Glove while batting .327 with a .953 OPS — the highest in his big-league career. He was third in MVP voting. So, suffice it to say, he would have had higher salary demands at that point. And the AAV ask would only have grown after that.

As it is, the Pirates have given out one contract with more guaranteed money than McCutchen’s extension: Jason Kendall’s six-year, $60 million deal in 2000. Sure, McCutchen might have agreed to an extension later down the line, during his arbitration years, like Matt Kemp — another one of McCutchen’s top comps on Baseball-Reference — did, signing an eight-year, $160 million extension with the Dodgers a year before he qualified for free agency. But there’s no reason to believe Nutting would have been willing to open his pocketbook to pay a fully established star. He has not done so yet.

Trade him: From the moment McCutchen signed the extension, his time with the Pirates was most likely to end via a trade. Sam Miller, formerly of ESPN, analyzed 67 extensions signed from 2010 through 2014 — all of which were signed when the player was two-plus years from free agency; covered at least four years; and bought out at least one year of free agency — and found that more than half of those players were traded before the extensions ended.

Now, let’s say McCutchen hadn’t signed. Huntington tended to trade players with a year or two of club control left. Moving McCutchen at some point in 2014 or 2015 would have brought back an incredible haul of prospects, even with his salary climbing in his arbitration seasons. (The Pirates would not, however, have Bryan Reynolds and Kyle Crick, whom they acquired by trading McCutchen to San Francisco.) But trading McCutchen in 2014 or 2015 would also have brought another thing: Rage. White-hot rage. Because the Pirates were back. Fans had endured two decades of losing to finally see the Pirates in the playoffs in 2013. So, maybe Huntington would have opted to …

Let him walk: Unwilling or unable to afford a monster contract for McCutchen, and understanding how unpopular it would have been to trade him away from a postseason contender, the Pirates probably would have settled for extending McCutchen a qualifying offer to add a draft pick. It’s little consolation for losing a player of McCutchen’s caliber, but better than nothing.

Back to reality

If free agents are paid for past performance, extensions are for the future. Some work out like this, with an MVP making a long-term deal look awfully team-friendly through his prime. Some are the other way around.

Even if McCutchen left $85 million or more on the table, it’s hard to call his story a cautionary tale. (I mentioned the $115 million in career earnings, right?) At the time of the extension, it made sense for both sides. The team wanted cost certainty. The player wanted guaranteed money. Those desires haven’t gone away. While the $300-plus million free-agent contracts for Bryce Harper, Gerrit Cole and Manny Machado are obvious examples of why agents would avoid extensions, we still see stars-in-the-making signing them.

“Whenever you sign a long-term contract, whether it’s got options at the end of it or not, you’re potentially sacrificing some yearly income, but you’re buying security,” Andrew Zimbalist, an economist and professor at Smith College, explained when I phoned him in 2018.

Teams are making similar calculations, scouring comps and trying to translate a player’s early production into how he’ll perform in his prime. These are educated — and often outrageously expensive — guesses.

“Everybody’s trying to minimize risk and maximize value,” Zimbalist said.

McCutchen, now 34, admitted to the Inquirer that he has thought about what it would have been like to hit free agency on schedule in 2015. But, he said, he has no regrets about the extension. Who knows what might have happened without it? What if he had gotten hurt? What if he hadn’t put up those huge numbers after all? It was all part of the equation he had weighed with his agent. Coming from Fort Meade, Fla., a town where the median household income is $43,000, McCutchen knew that trading three years of free agency for immediate financial security was the right decision for him.

“I had choices to make,” McCutchen told the Inquirer. “I had to evaluate what risks I’d be taking if I waited. I thought about all those things, and I’m happy with what I did.”

(Top photo of McCutchen: Charles LeClaire / USA Today)

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