One day earlier this season, a seasoned big league reliever took stock of his career.

He has spent five years in the majors, handling his share of high-leverage innings and generally performing well. This coming fall, he is set to reach a magic number: six years of major league service, earning him the right of free agency for the first time in his career. He will hit the open market still in his prime, hoping to land a trifecta that he’s so far been denied – the ability to choose his employer, garner a long-term commitment and earn a salary determined by open competition for his services.

He’s not looking forward to it.

“You talk to some of your buddies that are in it and it’s a miserable experience,” the reliever told me recently, “because you don’t know where you’re going to go, no team wants to give you the value you think you’re worth, and you’re like, ‘Am I going to have a job? Where am I going to go? What am I going to do?’”

He is hardly alone. This spring, I’ve spoken to a number of players who are set to reach six years of service by the end of the 2024 season. They range from some of the best players at their positions to journeymen just hanging on, and all were granted anonymity so they could speak freely about approaching such a consequential milestone. For many, it will have taken a decade or more – of minor league seasons, of call-ups and send-downs and other detours – to finally have the ability to exert some control over their careers.

And they have mixed feelings about it.

They watched this past winter as standout players like Cody Bellinger, Blake Snell and others were forced to settle for pillow contracts rather than long-term guarantees. Juan Soto will make his bag this offseason, but after seeing the open market shun a two-time Cy Young winner and a former MVP, players on the verge of free agency can’t help but wonder how rudely it might treat them. Some are well over 30 years old, meaning they’ll reach free agency at ages for which teams are typically loath to pay. They’re hoping for the best, but several say free agency seems something less than it’s cracked up to be.

“Free agency this year was really strange,” said one hitter. “Super strange.”

“For the first time in a while,” said another, “it’s just not as clear what free agency can present to a player.”

“You feel like you’ve reached this part of your career where it’s a thing to celebrate,” said a pitcher, “and then you start to wonder, ‘Well, what am I going to be celebrating? What is this going to look like?’”

To reach this point requires mettle. Players have weathered meager minor league salaries, sudden employer changes and punishing arbitration hearings. Most players never get this far, but the ones who do are told they’ll be rewarded for completing the journey. The closer you get, though, the more a question begins to nag.

What if the promised land sucks?

…

When you’re a rookie, none of this seems real. The glow of the big leagues is intoxicating, and it’s easy to get drunk on the promise of a long and storied major league career. A rookie’s mind is either too overwhelmed to consider a possible business decision six years down the road, or too naïve to treat it as anything other than a fait accompli. You assume you’ll get there because nothing has yet told you it might not happen.

Or, more accurately, that it probably won’t.

“To bank on anything for six years,” said a pitcher, “is crazy.”

By the time players reach five years, they’ve inevitably learned this lesson. Almost all have struggled and been sent down. Some have been taken on and off the 40-man roster. Several have been waived or traded and had to start over, proving themselves to a new team. All the while, they’ve watched as a brutal process of attrition filtered out many of their teammates.

“It’s a long time to get to that free market,” said one player. “A high percentage of guys don’t make it past a year, and most guys don’t make it past three years.”

No one knows this better than a major league reliever. The ones I spoke to for this story all underscored just how fungible their position is. “If you’re down for a couple months, it’s just, ‘All right, see ya.’ We’re expendable,” said a middle reliever. Sometimes, said another, that means pitching “on a night you might be a little banged up” because the other choice may be pitching for nobody. “There’s really no room for error,” said a third. “You have to bring it every day.”

Though starting pitchers and everyday players enjoy a greater measure of certainty, laboring without a guarantee of future employment is kind of the gig. Reaching arbitration after three years provides a welcome bump in pay – “You always hear the saying, ‘Take it to ‘traish,’” said one reliever – but the process can be brutal. An arbitration hearing can amount to an hours-long critique of a player’s value, often in disagreement over just a few hundred thousand dollars. And even though it represents a player’s first real chance to advocate for his own value, much remains out of his control.

Performance in a player’s last pre-arb year carries outsized evaluative weight, locking them into a rough pay scale no matter how much they improve in future years. “I would have liked to have a better platform year,” said one hitter. At least you can control your platform year; there’s little influence to exert over others at your position in your service class. “If you get a guy who takes a bad deal from a team because he doesn’t have a good agent, or he doesn’t have any leverage and he just feels like he needs to take whatever deal gets offered,” said a pitcher, “the whole market gets reset.”

Still, that bad deal is at least guaranteed under the Collective Bargaining Agreement. Going to a hearing can be a matter of principle for players, but as many learned this spring, it exposes them to more risk. Some were alarmed that the Giants could cut an established player like J.D. Davis and pay him just a fraction of the salary he’d just won in a hearing; while negotiated one-year contracts for arbitration eligible players are fully guaranteed under the most recent CBA, that provision does not guarantee contracts reached through a hearing. There are no guarantees, it shows, until they’re written into your contract.

“At any time, the team can be done and decide to non-tender you,” a hitter said. “It still feels like you’re playing every year for your job the following year. It’s an incredible amount of stress. Nobody’s sitting here asking people to feel bad for us. But it makes it hard to let the best version of yourself show up every day when you’re constantly feeling like you’re playing for job security.”

No wonder the game has seen a run of young players agreeing to early-career extensions that are both lucrative and team-friendly. They land life-changing money and no longer have to trek the long and narrowing path to free agency. Though the players union stresses the importance of setting a player’s value on the open market, few who have had to grind just to reach five years begrudge anyone who took an early payday.

“Before approaching this personally, guys turning down big numbers, I flinched at it,” said one hitter. “I always understood the narrative that as a union, as an association, we have to move the needle for the wave of players after us. I get that. But it was hard for me to see early in my career because I felt like so much needed to happen between now and then.”

These players are much closer now, but a lot still could happen to derail them. If they struggle, they could be designated for assignment and released or outrighted to the minors before crossing the six-year threshold. If their team falls out of the playoff picture, a trade becomes more likely, uprooting players and their families in the middle of the year. An injury – an ever-present risk, especially for pitchers – would guarantee them service time but tank their value at the worst possible moment.

Then, even if they survive that final gauntlet to reach the open market, they may get their asses kicked. Players feel strongly that it shouldn’t be that way – “It’s hard to get there, and if you do, you should get paid for it,” one pitcher said – but they’re also pragmatists who know better than to stand on stubborn principle. If the open market isn’t going to treat you well, because you’re too old or because your position is too expendable or because teams just don’t want to spend money that particular winter, then maybe a team-friendly extension in the hand is worth more than a lucrative deal in the free-agent bush.

“It would be silly and a little bit irresponsible,” said one hitter, “to not take that into account.”

…

This isn’t to say free agency has lost all its luster, of course. “Agency” is the key part of the term. Not all free agents will get paid, at least not as much as they’d hope, but all of them will get to choose.

For so long, players don’t have that luxury. In what other profession can someone go a decade or more without having any choice about where to work? The current system has been codified in the CBA for decades – and was even more restrictive before the players organized – so it may be easy to take its effects for granted. But not when you’re on the precipice of finally being able to make decisions about your own career.

“It’s crazy. I’ve had zero say where I’ve been for 14 years,” said one pitcher. “To have the opportunity is probably what players look forward to the most.”

They’d like to get paid, too, either in free agency or earlier in their careers. To that end, the players offer varying solutions, some more attainable than others.

Everyone would like a shorter runway to free agency – “Maybe two years of league minimum and two years of arb,” said one hitter – although the players as a whole might not like the concessions the owners would demand to secure such an overhaul. Those who have been closer to the bargaining process know that. “Everybody would love to get to free agency sooner,” said a hitter who says he keeps up with the union’s efforts. “Is it realistic? I don’t know.”

The latest CBA did do more to funnel money to pre-arbitration players, raising the minimum salary and establishing a bonus pool to be distributed among top performers. One pitcher noted most of the players receiving that money are the uber-talents who are already likely to be offered lucrative extensions or land large free-agent deals, but others pushed back on such criticism. “More can always be done,” a hitter said. “But I do think the system is pretty good.” Another wouldn’t change a thing, despite having been released at one point in his arbitration years. Reaching six years is supposed to be hard. “The system in place, it’s been there for a while and a lot of guys have gone through it,” he said. “Like everything in the game, you’ve got to earn it.”

One solution that generated discussion amidst the sluggish spring was the idea of a signing deadline. The union has never advocated for such a measure publicly, and Scott Boras, the game’s most powerful player agent, has lambasted it as a giveaway to ownership; it’s perhaps telling that commissioner Rob Manfred was the one to float the idea. Still, with players having watched their colleagues hang on the open market deep into March, their curiosity about the benefits of a deadline hasn’t evaporated.

“That’s the thing I’ve been hearing mostly,” a pitcher said, “and it seems like there’s maybe some traction there.”

Even if a deadline wouldn’t be sound policy – teams can choose to not spend rather than embroil themselves in a bidding war, but free agents can’t realistically take their talents to another professional league – its lingering popularity demonstrates how much the specter of this past winter clouds the minds of players approaching free agency for the first time. They want the right of free agency, but they want it to be worth it. They don’t want to sit at home for months wondering where they’ll play, only to settle for a short-term deal that lands them in the exact same predicament a year later. No one wants to join the Boras Four.

Still, as poorly as those free agent forays went, those players still got to choose their employer. That’s what players covet as much as anything. “You used to hear this all the time as a player, that the goal was free agency,” said one pitcher. He offers an amendment to that, though: “Six years is the goal, but six years while still having more than one team interested in you is the goal.”

That pitcher is a reliever, one who knows that even at his best, he’s likely to live the rest of his career off one-year deals. But if a player is good and lucky and happens to time the market just right, it’s possible to fully grasp that brass ring. Not every free agent cashes in, but some do.

“I imagine if you’re coming off finishing six and having a good year,” said one hitter, “it’d be pretty fuckin’ cool.”

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