Last season, many were watching for Juan Soto, as he was expected to be the biggest free agent in baseball. Many were expecting him to sign for a deal that was more than $500 million in total value. Then, the playoffs happened. Soto led the New York Yankees to the World Series, helping his team overcome an epic Aaron Judge slump. That performance inflated his value further, and he eventually signed across the street with the New York Mets for $765 million over 15 years.
Nobody can argue that he didn’t earn an extra addition of generational wealth due to one postseason performance. The same applies to Pete Alonso, who signed a two-year contract worth $54 million (although he has the option to opt out this season). He had a home run and three RBIs in a do-or-die Game 3 against Milwaukee in the Wild Card round. He had two home runs in four games against their rivals, the Philadelphia Phillies. In Game 5, with the Mets facing elimination in the NLCS, Alonso had a home run, three RBIs, and four runs against the Dodgers.
Playoff performances often equal high prices. This season, free agency isn’t as top-heavy as last season. There are a ton of top free agents on playoff teams, and they can add some zeros to their paycheck if they show up in October.
1. Luke Weaver, New York Yankees
Luke Weaver was one of the darlings of the New York Yankees last season. Taking over for the struggling Clay Holmes, Weaver was nails in the postseason. He appeared in a ridiculous 12 postseason games, finishing with a 1.76 ERA. How did the Yankees repay the man? They traded for once-star closer Devin Williams in the offseason.
Many say the Yankees were spending some of the money they would have given to Juan Soto, but this was money not well spent. Williams has been awful since coming to the Yankees. He’s lost his closer role multiple times, and the Devils traded a fortune to get more bullpen help. They traded for Camillo Doval and David Bednar in separate trades. It was supposed to make this the best bullpen in baseball. Turns out, they both can’t pitch in New York.
You know who can pitch in New York? Luke Weaver.
We know how this ends. Weaver will get the ball when it matters most. Can the Yankees go on another run to the World Series? If they do, it’s hard to believe that anyone besides Luke Weaver is closing out games. And with that, he could earn himself a legendary payday.
2. Kyle Schwarber, Philadelphia Phillies
The market for Kyle Schwarber is hard to pin down. Many believe he will get a deal in the 3-4 year range, but the price isn’t easy to predict. His most significant issues are age and position. He’s a 33-year-old designated hitter. That is still somewhat desirable, given the 30 starting DH spots in the league, but it does limit a manager’s ability to adjust the lineup.
Schwarber is already close to being undeniable as a hitter. However, some might think he’s just a product of Philadelphia. He was somewhat of a journeyman before coming to the City of Brotherly Love. Prior to coming to Philly, he was expecting to hit 30 home runs per season, but that immediately jumped to over 40. In his four seasons with the Phillies, he’s hit 46, 47, 38, and 49 home runs. That 49 is about to break 50 with a few weeks of games left to play.
Someone is going to pay Schwarber, but they might have some contingencies in the contract. If he puts on a ridiculous performance in the postseason, he will crush it in the free agent market. If we see another 1.000 OPS and the Phillies beat the Dodgers on the way to the World Series, that hype train will lead to a money train.
3. Alex Bregman, Boston Red Sox
We avoided most of the opt-out candidates on this list, but there’s too much smoke around Alex Bregman’s future to ignore him on this list. Most would say the market for Bregman took too long to materialize, and the Soto contract really took the air out of the market. Too many were focused on that, even if they weren’t one of the most likely teams to sign him.
Bregman has had an interesting start to his Red Sox career. The former third baseman and franchise player, Rafael Devers, was reportedly not happy with his signing, refusing to play anything but third base. Then, the Red Sox shocked the world when they traded Devers to the San Francisco Giants.
It would be some of the worst mismanagement we’ve ever seen for the Red Sox to go from two top third basemen to none in the matter of one season, but we’ve seen crazier from this ownership group. To get the most out of his time in Boston, Bregman has to perform in the postseason.
Right now, the Red Sox have a five-game lead on the Texas Rangers, who are the first team outside the postseason picture. They are relatively safe barring a collapse. Bregman should have a chance to raise his price in the postseason if he helps the Sox make an unlikely run.
4. Framber Valdez, Houston Astros
The Houston Astros aren’t exactly throwing out Gerrit Cole and Justin Verlander as their rotation leads, but they still have their ace. Framber Valdez is going to take this Astros team places. Unfortunately, the places he’s been taking the Astros as of late are not positive. His disagreement with catcher Cesar Ruiz took over all of the headlines, and his reaction to the moment made it worse.
What’s the best way to get over a controversy? Dominate when it matters the most.
Valdez has a unique opportunity that few pitchers get in their careers. He has tens of millions of dollars on the line this postseason. If Valdez puts together an insane performance and leads the Astros to the World Series, he is going to get a contract that surprises some people.
Valdez is 31 years old. This is his only chance to cash in on his career. This season went about as poorly as it could have without an injury or full-scale crash-out. Still, the Astros are one of the favorites to make the World Series this year as the leaders of the AL West. If Valdez brings them there, then he’s getting a payday.
5. J.T. Realmuto, Philadelphia Phillies
The catcher position is insanely weak across baseball. Cal Raleigh is the standard bearer for great catchers, hitting 53 home runs this season. He’s in the MVP conversation partially because of the position he plays. So, when one of the great catchers of this era becomes available, he will likely cash out, even if he’s 34 years old.
J.T. Realmuto is the best option on the market for catchers. That alone is going to get him a good contract, but if he does crazy things in the postseason, he could add years to his deal. That’s where he will have to do some convincing.
We think teams won’t have a problem hitting Realmuto’s price, but they’ll want to do it for 2-3 years. He will want a longer deal without sacrificing cash. If he shows he can be an elite hitter not considering position, then the league will be willing to extend their deals knowing they can move him to DH or first base later in his career.
Realmuto has to shake off the stink of last postseason. He was about as bad as you could possibly be, going 0-for-11 at the plate during the Phillies' short exit. With that hovering over his head, he has to showcase the best of himself for any team, including the Phillies, to pay up.
6. Bo Bichette, Toronto Blue Jays
The Toronto Blue Jays have shockingly led the AL East for most of the second half of the season. They’ve held off the Yankees and Red Sox, mostly on the backs of his powerful offense. The Jays have scored the second-most runs in the American League. And they’ve done that without the long ball, which can be unpredictable in the playoffs. While the Yankees have needed 243 home runs to lead the league in runs, the Blue Jays have only needed 174 to come in second.
And it’s thanks to the clutch hitting of guys like Bo Bichette and Vladimir Guerrero Jr. The nepotism pair have both played incredibly well this season. Guerrero already earned his contract extension, but Bichette is still staring free agency in the face.
Bichette is hitting .319 with 94 RBIs this season. Someone is going to give him a rich contract this offseason. Bichette is just 27 years old, and he is past his struggles from last season. Bichette looks like he could be a superstar for the next decade.
Will someone pay him like he is? This is a contract that might have the most variance. Bichette could peter out in the playoffs and give other GMs pause. Then again, he could put up similar numbers to what he’s done in the regular season. If the Blue Jays make the World Series, they will have all of Canada on their side. It will have insane viewership, and it could revitalize baseball in the country. That’s worth quite a lot of money.
7. Gleyber Torres, Detroit Tigers
Gleyber Torres is in an interesting situation. After helping the Yankees get to the World Series last season, New York seemed perfectly fine with letting him go. Their appoplecy regarding his status hurt his market. There’s no other way to say it.
The Yankees let him go for a one-year, $15 million deal, and no Yankees fan was that upset over it. Of course, they were more upset about Soto leaving, but Torres was once considered one of the most talented young players in baseball. He was the top prospect for the Yankees during their short rebuild, coming over in the Aroldis Chapman trade.
Torres has been better this season. He will likely break 70 RBIs and made the All-Star team. Going into the playoffs, he could prove to be a worthwhile power hitter at a position not known for big numbers there.
Torres is still not the guy many thought he would be coming up in the Cubs system, but he is a great major leaguer. If he can put the Tigers, who have fallen under the radar as the leaders in the AL Central, on the map with a big performance, he could earn himself money like he’s never seen. He is still just 28 years old.
8. Luis Arraez, San Diego Padres
The San Diego Padres haven’t been in the headlines as much as a team with its level of stardom should be. But, at the time of this writing, the Padres are just one game behind the Dodgers for first place in the NL West. This is despite the fact the power numbers have dried up completely this season. Only the Pittsburgh Pirates have fewer than the Padres’ 127 home runs.
It doesn’t matter how; it just matters if when it comes to making the playoffs. Once a team gets there, then anything can happen. Can the power numbers return for the Padres, and who could be the catalyst for that jump?
Luis Arraez isn’t going to hit the home runs, but he is going to make those home runs much more impactful. The 28-year-old is not having one of his most productive seasons, hitting just .285 after winning multiple batting titles. Someone will still give him a pay raise, but it won’t be the raise he would have received if he were a free agent last offseason.
That is, unless we see that previous hitter in the postseason. Last postseason, he had seven hits, and they were all singles. He needs to do better this year, especially if the Padres and Dodgers face off again. If he helps his team beat their rivals and the World Series favorites, he will get himself a long-term deal, probably from the Padres.
9. Dylan Cease, San Diego Padres
Sticking with the Padres, Dylan Cease was supposed to be the guy who brought the Padres' rotation closer to the Dodgers. He hasn’t been close to that. His 4.71 ERA is the worst he’s pitched since his rookie year. Cease is coming into his free agency year with more questions than answers.
Cease was bad in his one start for the Padres in the playoffs last season. He needs to show he can be the guy for a team. If he makes three starts and dominates in all three, a team is going to give him a regrettable contract.
This actually should focus on if Cease actually has the ability to pitch in these big moments. Does he have that impact that we thought he could when he was traded to San Diego? Is that the type of pitcher he is?
Cease can show he’s worth a big contract? The playoffs are his last chance before he hits the market.
10. Trent Grisham, New York Yankees
Trent Grisham is one of the surprises of this MLB season. The Yankees center fielder has taken one of the most difficult positions in sports, and he’s excelled despite a lack of fanfare around his status. The Yankees lost Soto in the offseason, and they replaced a portion of his impact through Grisham.
As of this writing, Grisham has 30 home runs and 64 RBIs. But it’s the postseason where legends are made in the Bronx. He didn’t play in the postseason for the Yankees last season. This year, he’s imperative to their success.
Grisham could become a legend for the Yankees, who actually have a scary amount of free agents in their lineup. Along with Grisham, Cody Bellinger and Paul Goldschmidt are both expected to hit the market. But Grisham, seemingly out of nowhere, could outearn them in free agency.
He can secure that with a big postseason. If the Yankees get back to the World Series, one would assume Grisham is playing well at the top of the Yankees’ lineup. Can he provide what they’ve needed in terms of clutch hitting? That would only help his case.