Playing Matchmaker with MLB's Top Remaining Free Agents

It has officially gotten weird that four of the top 10 players in this year's Major League Baseball free agency cycle still have not signed with anyone.

However, it's not unprecedented for nine-figure contracts to be signed even later in the offseason than this.

Back in 2018, J.D. Martinez signed his five-year, $110 million deal with Boston on February 26. The following year, Bryce Harper's $330 million contract with Philadelphia didn't happen until February 28. Harper's contract was signed one week after Manny Machado signed his $300 million deal with San Diego. And thanks to the lockout, Nick Castellanos, Freddie Freeman, Kris Bryant and Trevor Story all signed their nine-figure deals in mid-March 2022.

Eventually, Blake Snell, Cody Bellinger, Jordan Montgomery and Matt Chapman are going to sign somewhere. So are the likes of Martinez, Mike Clevinger and other quality free agents who are still available.

But let's play one more, perhaps final round of free agency matchmaker while we wait.

Recent rumors will factor into these matches, where applicable. But just as important are team needs/roster fit and the ability to actually afford the player.

On the affordability front, there's obviously no salary cap in baseball. However, we've averaged every team's payroll from the past three years, added a 10 percent "inflation bump" and subtracted from that the current projected payroll to make a rough estimate of what each team is willing to spend. It's far from an exact science, and there's always the possibility of a Shohei Ohtani-style, drastically deferred contract to make things work. But it does give us a decent idea who still has money to spend.

2023 Stats: .307/.356/.525, 26 HR, 97 RBI, 20 SB

Devoid of any actual rumors about where Cody Bellinger might be leaning toward signing, there has been a growing speculation that he'll end up back with the Chicago Cubs.

From a roster perspective, it's an obvious reunion. Chicago's first base situation is decidedly not great, and it could use another option in center if Pete Crow-Armstrong's April is anywhere near as disappointing as his extremely small sample size of play in September.

Can the Cubs afford to bring Bellinger back, though?

Based on that calculation mentioned in the intro, the Cubs are already $10.5M above "budget." And while that factors in the 2021 and 2022 seasons when they were kind of in rebuilding mode, their current 2024 payroll of $187.98M is less than a million bucks behind the $188.9M payroll they had in 2023.

Adding a Bellinger-sized contract to the mix would push them up close to or possibly beyond $210M, which doesn't include the five-year, $40M deal they gave Craig Counsell to be the manager.

Could they conceivably handle that payroll? Sure. But they've never gone north of $204M on Opening Day before, and they might be reluctant to do so when they are maybe the top candidates to win the NL Central without making any more moves.

And if it's not the Cubs, the Giants make the most sense.

With a current payroll of just $134.3M, San Francisco is almost $30M below its lowest payroll of the past three years, and has more than $57M left to spend based on our calculations.

Spoiler alert: They could afford to sign two of the four big names still available.

But Bellinger might be the best fit of the bunch, because of his 1B/CF versatility, because of his ability to bring some star power to a lineup that has been lacking it for years and because of how well he hit against the Dodgers last season. If he spends the rest of his career with a Los Angeles-sized chip on his shoulder for non-tendering him last offseason, it'd be great to have him in the NL West.

Bellinger's Match: San Francisco Giants

2023 Stats: .240/.330/.424, 17 HR, 54 RBI

Even before this lingered throughout the entire offseason, Matt Chapman's market always seemed destined to be the weirdest of the big ones.

Top-tier third basemen—Manny Machado, Nolan Arenado, Rafael Devers and Anthony Rendon, the latter of whom at least seemed top tier when he signed his deal—get PAID. As far as AAV is concerned, those are four of the 15 highest-paid players in baseball.

But Chapman isn't on that tier. He has a phenomenal glove, but he's a career .240 hitter who turns 31 in two months and has already lost his slugging prowess from a few years ago.

At this point, even an AAV down in the $20M range to match an Austin Riley, Alex Bregman or José Ramírez might be a bit excessive, especially on a contract spanning at least half a decade.

But $20M is probably on the low end of the range that Scott Boras is seeking for his platinum-gloved client, so here we are.

On the Venn Diagram of "Needs a 3B," "Has at least $20M to spend" and "Realistically expects to contend in 2024," the only plausible intersections are Detroit and San Francisco.

We already have San Francisco getting Bellinger, and though it's possible/likely they could get two of the top four still on the board, the Giants would want one of those signees to be one of the starting pitchers.

So, welcome to the Tigers, Chappy?

Detroit's $92.8M payroll is nowhere close to where it finished each of the past two seasons, with a theoretical $33 million left to spend. However, a big chunk of that was the Miguel Cabrera sunk cost that the Tigers aren't trying to replicate any time soon.

But if they can get Chapman on a five-year, $100 million type of deal, they just might do it.

Chapman's Match: Detroit Tigers

2023 Stats: 10-11, 3.20 ERA, 1.19 WHIP, 7.9 K/9

Jordan Montgomery's matchmaker pairing is so obvious that it is astounding the deal hasn't gotten done yet.

The Boston Red Sox have an estimated $54 million to spend. They desperately need another starting pitcher. Montgomery has had proven success in the AL East from his former time with the Yankees. And the real kicker is that his wife reportedly started her dermatology residency at a hospital in Boston, so he's going to be spending a lot of time in Massachusetts anyway.

It's really just a question of whether Boston will offer Monty a fair deal or if the Red Sox are going to try to lowball him, knowing that the fit makes sense.

The Texas Rangers have also been expected to want to bring Montgomery back, although they have been unable/unwilling to do anything substantial this offseason in light of the regional sports networks fiasco. Diamond Sports Group reportedly reached a bankruptcy-avoiding agreement with the Rangers (among others) earlier this month, but that didn't exactly open any floodgates. All they've added since then are a couple of minor-league contracts.

Do they still need a healthy starting pitcher? Absolutely. With Jacob deGrom, Max Scherzer and Tyler Mahle all out for the first few months of the season, bringing in Montgomery would be massive.

But there's still long-term uncertainty with the RSN stuff, so giving him a six-year, $150M type of deal might not be in the cards.

Could they go all-in for one year to out-bid the Red Sox, though?

Maybe give him $40M with an equal-sized player option for 2025, allowing Montgomery to bet on himself in a way instead of waiting to see if a long-term deal is coming?

Texas currently has a $215.7M payroll, but it finished last season north of $251M.

Still feels like Boston is the choice if it's a long-term deal, but Texas could swoop in on a short-term contract.

Montgomery's Match: Boston Red Sox

2023 Stats: 14-9, 2.25 ERA, 1.19 WHIP, 11.7 K/9

By now, you probably have Blake Snell's "resume" memorized, as we've been talking about him nonstop for months. The two-time Cy Young winner is a fantastic strikeout artist who walks a few too many hitters (especially this past season) and has logged at least 130 innings in a season just twice in his career.

He wants a contract worth $200 million-plus, which is perfectly understandable for a two-time Cy Young winner. But there's enough risk involved here that even the deep-pocketed Yankees decided the price tag for Snell was too rich for their blood before pivoting to Marcus Stroman.

The two biggest candidates on the board for Snell have been the Giants and the Angels. But with Angels owner Arte Moreno saying recently that the team plans to operate with a lower budget in 2024, it might just be a stalemate between Snell and the Giants to see who blinks first.

San Francisco has always been the most logical landing spot for Snell. He has outstanding career numbers at Oracle Park (albeit in only four career starts), and it just makes a lot of sense for a walk-heavy pitcher to make his home starts in the league's most cavernous stadium to help mitigate the damage that could come from home runs.

It does bear mentioning that San Francisco committed 15 more errors than any other team in 2023. Combining BBs with ROEs could lead to a lot of long innings and unearned runs. And Snell already almost never pitches into the seventh inning of his starts.

But given how well he has pitched against the rest of the NL West over the past three years, San Francisco has to have a lot of interest in Snell, provided it is serious about trying to win in 2024.

Snell's Match: San Francisco Giants

2023 Stats: .271/.321/.572, 33 HR, 103 RBI

The Bellinger-Chapman-Montgomery-Snell quartet has been dubbed the "Boras Four," as the four primary free agents still out there are all represented by Scott Boras in their quest to secure a nine-figure contract.

But J.D. Martinez makes it more of a Boras 4.5 as the clear fifth-best player still available, albeit one who will turn 37 this offseason and is probably going to get a two-year deal, at best.

Martinez is no stranger to waiting out the market. As previously noted, it was later in the calendar than this when he signed his $110 million contract back in 2018.

However, finding a team with around $15 million to spend on a guy who is purely a DH at this point in his career isn't easy.

If we didn't already have both Bellinger and Snell going to the Giants, San Francisco would make sense. And while both the Red Sox and Dodgers could find the money to bring back Martinez, they each already have a full-time DH. Same goes for the Phillies.

Perhaps this is where the Angels finally make some sort of attempt to replace Shohei Ohtani?

Aside from signing Aaron Hicks for next to nothing and Mike Moustakas to a minor-league deal, the Angels have done nothing to address the two-time-MVP-sized hole in their lineup. Though we previously mentioned Arte Moreno's comments about having a lower budget in 2024, there's a fine line between spending over $200 million on a Snell or a Bellinger and spending less than $20 million on Martinez.

Also, LAA's current payroll ($157M) is drastically below where they finished last season ($230M). They could bring in Martinez and still spend about $50M less than they did in 2023.

Martinez's Match: Los Angeles Angels

These buckets of "left-handed hitters," "right-handed hitters" and "pitchers" are nowhere near a comprehensive list of the unsigned free agents. But if you're putting together a "top 20 still available" list, these guys plus the big five are the logical names to include.

Brandon Belt, 1B
Matchmaker Pick: Toronto Blue Jays

Among players with at least 200 plate appearances in 2023, Belt led the Blue Jays in both slugging and OPS. And though they did sign Justin Turner, they could use an inexpensive, left-handed DH/backup 1B option.

Eddie Rosario, OF
Matchmaker Pick: Kansas City Royals

The Royals have put in a lot of work this offseason, including signing Hunter Renfroe to man right field. But their outfield situation in 2023 was just plain bad. Adding another relatively well-established outfielder could be huge. And Rosario making a return to the AL Central—where he earned AL MVP votes in both 2019 and 2020 with the Minnesota Twins—could be fun.

Joey Votto, 1B/DH
Matchmaker Pick: Cleveland Guardians

After 17 seasons in Cincinnati, it'd be great if Votto could at least stay in Ohio. And goodness knows the Guardians could use a DH after a 2023 campaign in which they hit 27 fewer home runs than any team. They can't afford to bring in a marquee bat, but Votto on a one-year, $6-7 million type of deal is doable.

Kolten Wong, 2B
Matchmaker Pick: Washington Nationals

The rebuilding Nationals have honed in on the approach of signing reclamation projects to one-year deals and hoping to flip them for prospects at the trade deadline. It worked out wonderfully with Jeimer Candelario last year, and that's pretty clearly the goal in signing Joey Gallo to a one-year deal this winter. Maybe Wong could be a good four-month fit for a team that doesn't exactly have a sure thing at second base.

Tim Anderson, SS
Matchmaker Pick: Miami Marlins

No need to re-invent the wheel here. We heard a few days ago that the Marlins made an offer to Anderson, which makes a lot of sense for a team with neither a sure thing at shortstop nor a great source of OBP aside from Luis Arraez. Anderson had a brutal 2023 campaign, but maybe he can resurface as an All-Star SS on a one-year deal in Miami.

C.J. Cron, 1B
Matchmaker Pick: Chicago Cubs

Ideally, they'll re-sign Cody Bellinger to serve as the primary first baseman. But if that falls through, Cron could be a solid backup plan. He's coming off a rough season in which he only played 71 games due to injury, but he has been a solid source of home runs everywhere he has landed throughout his career.

Adam Duvall, OF/DH
Matchmaker Pick: Colorado Rockies

With Kris Bryant transitioning to full-time first-base duties, the Rockies could use at least one more outfielder. And Duvall's bat would fit nicely in that thin air in Denver. In 69 career plate appearances at Coors Field, he has seven home runs and 13 extra-base hits.

Amed Rosario, SS
Matchmaker Pick: Atlanta Braves

Atlanta needs a versatile bench bat for injury insurance purposes. And while Rosario has predominantly played shortstop throughout his career, he has also spent time at second base, as well as in both left and center field. They might have a few leftover (Eddie) Rosario jerseys lying around, too.

Michael A. Taylor, CF
Matchmaker Pick: San Diego Padres

The Padres recently signed Jurickson Profar, but they still desperately need at least one more outfielder—preferably a center fielder with legitimate range to take the place of Trent Grisham. Signing Taylor is such an obvious move for San Diego that it is shocking it hasn't happened yet.

Mike Clevinger, RHP
Matchmaker Pick: San Diego Padres

The Padres have relentlessly slashed team salary this offseason, getting their 2024 payroll ($145M) more than $100M below where it ended up last year ($256M). But they are still trying to win, right? And an established starting pitcher beyond Yu Darvish and Joe Musgrove would be a big help. A reunion with Clevinger should be on the table.

Michael Lorenzen, RHP
Matchmaker Pick: Baltimore Orioles

With Kyle Bradish out indefinitely with a UCL sprain and John Means a bit behind schedule this spring, the Orioles need to add a starting pitcher even more than they already did a week ago. Paying for Snell or Montgomery isn't happening, and even Clevinger might be out of their budget range. But Lorenzen should be doable.

Jake Odorizzi, RHP
Matchmaker Pick: Texas Rangers

Pretty serious no-brainer pick here. The Rangers traded for Odorizzi last offseason, but he was unable to pitch in 2023 due to injury. And now Texas needs an arm to help it tread water until all of its injured starters are able to take the mound. Classic spot for a one year plus player option deal for an almost 34-year-old returning from a lost season.

Hyun-Jin Ryu, LHP
Matchmaker Pick: Pittsburgh Pirates

Over the past two offseasons, Pittsburgh has made quite the habit of signing...let's call them elderly statesmen...to one-year deals. And the almost 37-year-old Ryu could be a solid addition to what has quietly emerged as a decent starting rotation. If he still has a good year left in the tank, pairing Ryu with Mitch Keller, Martín Pérez, JT Brubaker, Bailey Falter and Marco Gonzales could make things a little interesting in the NL Central.