10 MLB Free Agents with the Most Risk Attached

10 MLB Free Agents with the Most Risk Attached
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1Honorable Mentions
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2Clayton Kershaw, LHP, Los Angeles Dodgers
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3Miguel Sanó, 1B/DH, Minnesota Twins
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4Michael Conforto, OF, Free Agent
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5Martín Pérez, LHP, Texas Rangers
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6Brandon Drury, Utility, San Diego Padres
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7A Quartet of High-Priced, Middle-Aged Relief Pitchers
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8Aaron Judge, CF/RF, New York Yankees
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10 MLB Free Agents with the Most Risk Attached

Kerry Miller
Oct 20, 2022

10 MLB Free Agents with the Most Risk Attached

NEW YORK, NY - OCTOBER 18: Aaron Judge #99 of the New York Yankees hits a home run in the second inning during the game between the Cleveland Guardians and the New York Yankees at Yankee Stadium on Tuesday, October 18, 2022 in New York, New York. (Photo by Mary DeCicco/MLB Photos via Getty Images)
NEW YORK, NY - OCTOBER 18: Aaron Judge #99 of the New York Yankees hits a home run in the second inning during the game between the Cleveland Guardians and the New York Yankees at Yankee Stadium on Tuesday, October 18, 2022 in New York, New York. (Photo by Mary DeCicco/MLB Photos via Getty Images)

This MLB offseason's class of free agents is just plain loaded with talent. There are superstars up top in Aaron Judge, Jacob deGrom and Trea Turner, but you could put together a top 50 of this year's class and still omit at least a half-dozen outfielders and a half-dozen relief pitchers who will feel like major acquisitions wherever they land.

But not all of those free agents are going to shine in their new threads, and some of those top targets come with a lot more risk than others.

Whether because of injury history, age, inconsistent production or a combination of all three, we've put together a list of the 10 riskiest free agents.

That doesn't mean we think these guys will be busts, but there's justifiable concern that they won't be able to live up to the cost of what either might be or absolutely will be huge contracts.

Players are listed in no particular order, though four of them are grouped together in one section for reasons that will become clear when you get there.

Honorable Mentions

NEW YORK, NEW YORK - OCTOBER 09: Edwin Diaz #39 of the New York Mets throws a pitch against the San Diego Padres during the eighth inning in game three of the National League Wild Card Series at Citi Field on October 09, 2022 in the Flushing neighborhood of the Queens borough of New York City. (Photo by Dustin Satloff/Getty Images)
NEW YORK, NEW YORK - OCTOBER 09: Edwin Diaz #39 of the New York Mets throws a pitch against the San Diego Padres during the eighth inning in game three of the National League Wild Card Series at Citi Field on October 09, 2022 in the Flushing neighborhood of the Queens borough of New York City. (Photo by Dustin Satloff/Getty Images)

In addition to the ensuing 10 with a ton of risk attached, here are a few others for whom you have to wonder if the return on investment will be worth it, listed in alphabetical order.

Mike Clevinger, RHP, San Diego Padres ($8.5 million in 2022): Clevinger missed all of 2021 while recovering from Tommy John surgery, and this year both the velocity on his fastball and the break on his slider were nowhere near what they used to be. He turns 32 in December, but maybe he settles for a one-year "prove it" deal before trying to get a multiyear deal next offseason.

Edwin Díaz, RHP, New York Mets ($10.2 million in 2022): He's going to get paid like he's the best reliever in baseball, because he was this season. But throughout his career, Díaz has been really good in even-numbered years and nothing special in the odd ones. There's no logic behind it, but it's worth remembering that we've previously seen him flourish in one season and then wilt in the next.

Joey Gallo, LF/DH, Los Angeles Dodgers ($10.28 million in 2022): Is it really a risk or just an acceptance that you're paying for a guy coming off a lackluster slugging year who is likely to finish any season with more than twice as many strikeouts as hits? Gallo only turns 29 in November, though, so it won't be a surprise if someone gives him a contract on par with what Jorge Soler got last offseason (three years, $36 million).

J.D. Martinez, DH, Boston Red Sox ($19.35 million in 2022): Martinez is 35 now and is no longer the power hitter that he was from 2015-19. He's still a good enough hitter to be worth an eight-figure, one-year deal, but any sort of multiyear contract could be a disaster.

Brandon Nimmo, OF, New York Mets ($7 million in 2022): Nimmo picked a fantastic time to have the best season of his career. With the exception of Aaron Judge, there's a case to be made that Nimmo is the best outfielder in this year's free-agent class. But we're talking about a career .269 hitter with modest power, so it would be wild if he ends up getting Kyle Schwarber, Nick Castellanos or Starling Marte money ($20-ish million per year on four- to five-year deals).

Carlos Rodón, LHP, San Francisco Giants ($21.5 million in 2022): Rodón was awesome in both 2021 and 2022, but his lack of durability from 2017-20 (41 starts) has to at least come into consideration for any team thinking about paying his supposed market value of $126.6 million for four years.

Dansby Swanson, SS, Atlanta Braves ($10 million in 2022): Like Nimmo, Swanson is a solid player who finally put it all together at the right time. He's one of four big-name shortstops hitting free agency this offseason, although he's pretty clearly a step behind Trea Turner, Carlos Correa and (if he declines his player option) Xander Bogaerts. Whether he's actually worth $25 million (or more) per year remains to be seen.

Noah Syndergaard, RHP, Philadelphia Phillies ($21 million in 2022): Syndergaard was...fine. And he didn't get hurt. That was the main goal of this season after missing almost all of both 2020 and 2021. But he wasn't the Thor of old, but the 30-year-old is surely going to want a long-term deal anyway.

Clayton Kershaw, LHP, Los Angeles Dodgers

Los Angeles, CA - October 12: Los Angeles Dodgers starting pitcher Clayton Kershaw delivers a pitch during the second inning in game two of the NLDS against the San Diego Padres at Dodger Stadium on Wednesday, Oct. 12, 2022 in Los Angeles, CA.(Robert Gauthier / Los Angeles Times via Getty Images)
Los Angeles, CA - October 12: Los Angeles Dodgers starting pitcher Clayton Kershaw delivers a pitch during the second inning in game two of the NLDS against the San Diego Padres at Dodger Stadium on Wednesday, Oct. 12, 2022 in Los Angeles, CA.(Robert Gauthier / Los Angeles Times via Getty Images)

2022 Salary: $17.3 million

2022 Stats: 126.1 IP, 2.28 ERA, 0.94 WHIP, 9.8 K/9, 6.0 K/BB

After one of the most disappointing seasons of his career in 2021, Clayton Kershaw took a substantial pay cut on his one-year deal with the Dodgers. He had made north of $30 million in seven consecutive seasons, but he stayed in Los Angeles for $17 million (ending up making an additional $300,000 from incentives for number of games started.)

But in between his multiple trips to the IL (seemingly obligatory at this point in his career), Kershaw was fantastic.

He twice carried a perfect game through seven full innings, and he went at least seven scoreless innings in five of his 22 starts. Kershaw also finished the regular season strong, giving the Dodgers a 1.54 ERA in his final seven starts. (Although, his mediocre five-inning, three-earned run showing in Game 2 of the NLDS was the first step in San Diego pulling off the upset.)

Though his left arm has logged well over 2,500 career innings, he's only 34 years old, and even in that bad-by-his-standards 2021 campaign, he still had a respectable 3.55 ERA and rock-solid marks elsewhere (1.02 WHIP, 10.7 K/9, 6.9 K/BB). You have to go back to 2015 to find the last time he made at least 30 appearances in a season, but he is easily going to be worth more than $20 million—possibly close to $30 million—per season on the open market if he wants to keep pitching, which it sounds like he does.

Could this be a Tom Brady sort of situation in which leaving his team of 15 years sparks a Fountain of Youth discovery and an immediate championship in his new home, or could a new team (Texas Rangers?) end up paying $50 million for two years' worth of frequent injury updates and drastically reduced production?

Miguel Sanó, 1B/DH, Minnesota Twins

MINNEAPOLIS, MN - APRIL 23: Miguel Sanó #22 of the Minnesota Twins bats against the Chicago White Sox on April 23, 2022 at Target Field in Minneapolis, Minnesota. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images)
MINNEAPOLIS, MN - APRIL 23: Miguel Sanó #22 of the Minnesota Twins bats against the Chicago White Sox on April 23, 2022 at Target Field in Minneapolis, Minnesota. (Photo by Brace Hemmelgarn/Minnesota Twins/Getty Images)

2022 Salary: $9.25 million

2022 Stats: .083/.211/.133, 1 HR, 35.2 K%

In Miguel Sanó's first seven years in the big leagues, he clubbed 161 home runs, tied for 22nd most in baseball from 2015-21.

While some guys higher on the list did so in over 1,000 games played, Sanó got there in just 674 contests. In fact, he averaged 17.3 plate appearances per home run, tied with Shohei Ohtani (2018-21) as one of the more frequent round-trippers in the business.

But he struck out a ton (at least 34 percent every year), his defense was terrible and he wasn't a threat to do anything on the basepaths. His value was almost entirely derived from his 162-game paces of roughly 40 home runs and 100 RBI. And between a brutally slow start and a subsequent torn meniscus, he never came close to making that sort of impact in 2022.

Sanó is still only 29 years old, though. And while his MLB stats were deplorable this season, he did mash five home runs and batted .333 during a 13-game rehab assignment in July.

The power is clearly still there, but will anyone be willing to risk betting on a big bounce-back in 2023?

(Sanó does have a $14.25 million club option with Minnesota for next season, but it's somewhat of a foregone conclusion that they'll be paying the $2.75 million buyout instead.)

Michael Conforto, OF, Free Agent

ATLANTA, GA - OCTOBER 02: Michael Conforto #30 of the New York Mets reacts after hitting a ball deep for a home run during the eighth inning of the game against the Atlanta Braves at Truist Park on October 2, 2021 in Atlanta, Georgia. (Photo by Todd Kirkland/Getty Images)
ATLANTA, GA - OCTOBER 02: Michael Conforto #30 of the New York Mets reacts after hitting a ball deep for a home run during the eighth inning of the game against the Atlanta Braves at Truist Park on October 2, 2021 in Atlanta, Georgia. (Photo by Todd Kirkland/Getty Images)

2022 Salary: N/A

2022 Stats: N/A

Last offseason's lockout had a profoundly negative impact on Michael Conforto's bank account.

He declined the Mets' one-year, $18.4 million qualifying offer last November—this after reportedly turning down a nine-figure extension offer the previous spring—in hopes of a more lucrative offer.

Unfortunately he suffered a shoulder injury in January, and by the time teams were officially allowed to start negotiating with free agents again in mid-March, no one was willing to offer Conforto what he felt he deserved. So, instead, he underwent shoulder surgery in April, missed the entire season and will try his luck again this winter.

Conforto turns 30 in March, so there should still be plenty of good years left in the proverbial tank. However, what is the market going to look like for an outfielder who missed all of 2022 and who simply did not play well in 2021 (.232/.344/.384, 14 HR) prior to the injury?

Conforto hit 97 home runs from 2017-20, tied with Alex Bregman (in 43 fewer games played than Bregman) for 28th-most in baseball during that time. But higher on that list are Cody Bellinger and Christian Yelich, who seemingly never recovered from injuries, as well as Joey Gallo, Mike Moustakas and Marcell Ozuna, whose production each dropped off a cliff despite entering 2021 at 32 years of age or younger.

Is that enough cautionary tales to scare everyone away from making Conforto a big offer, or might he strike some sort of long-term deal that could be worth nine figures if he reaches some incentives?

Martín Pérez, LHP, Texas Rangers

ARLINGTON, TX - OCTOBER 3: Martin Perez #54 of the Texas Rangers pitches against the New York Yankees during the first inning at Globe Life Field on October 3, 2022 in Arlington, Texas. (Photo by Ron Jenkins/Getty Images)
ARLINGTON, TX - OCTOBER 3: Martin Perez #54 of the Texas Rangers pitches against the New York Yankees during the first inning at Globe Life Field on October 3, 2022 in Arlington, Texas. (Photo by Ron Jenkins/Getty Images)

2022 Salary: $4 million

2022 Stats: 196.1 IP, 2.89 ERA, 1.26 WHIP, 7.7 K/9

Martín Pérez will turn 32 in early April. In last year's free-agency cycle, similarly aged pitchers (up to one full year older or younger at the time) Anthony DeSclafani, Raisel Iglesias, Kevin Gausman, Marcus Stroman, Nick Martinez and Kendall Graveman each received contracts lasting at least three years with total values of $24 million or greater.

As one of just 14 pitchers to log at least 1,000 innings pitched dating back to the start of 2016, it's not an injury history concern that will keep Pérez from fetching a three-year deal worth close to $50 million.

Rather, it's a "can he repeat his 2022 dominance or will he revert to his 2014-21 mediocrity?" concern.

Prior to becoming an All-Star for the first time this season, Pérez had a 4.72 ERA and a 1.49 WHIP over the previous eight seasons. There were 73 pitchers who logged at least 800 innings pitched during that eight-season window, and he ranked dead last in ERA as well as dead last in WHIP among them.

Then again, Carlos Rodón had a similar breakout in 2021 after an injury-plagued and not-at-all-dominant run from 2015-20, and he got even better this season. It only takes one team to believe Pérez can do the same, but that team has to know it would be taking a huge risk if it guarantees Pérez eight figures per season for the next 3-4 years.

Brandon Drury, Utility, San Diego Padres

SAN FRANCISCO, CALIFORNIA - AUGUST 30: Brandon Drury #17 of the San Diego Padres at bat against the San Francisco Giants at Oracle Park on August 30, 2022 in San Francisco, California. (Photo by Lachlan Cunningham/Getty Images)
SAN FRANCISCO, CALIFORNIA - AUGUST 30: Brandon Drury #17 of the San Diego Padres at bat against the San Francisco Giants at Oracle Park on August 30, 2022 in San Francisco, California. (Photo by Lachlan Cunningham/Getty Images)

2022 Salary: $900,000

2022 Stats: .263/.320/.492, 28 HR, 87 RBI

Brandon Drury is the hitting equivalent of Martín Pérez.

For seven years, he bounced around the league, hitting just enough home runs and proving just versatile enough with his glove to keep getting chances, but never sticking anywhere.

Drury's Baseball Reference WAR from 2015-21 was minus-0.5. FanGraphs was a little more forgiving at plus-0.6 WAR. But, still, worth less than one-tenth of one win per season.

Then, out of nowhere, he started raking in Cincinnati. By the trade deadline, he was batting .274 with 20 home runs and a .520 slugging percentage. At the time, that was the 13th-best slugging percentage among qualified hitters, nestled just behind Nolan Arenado and just ahead of Anthony Rizzo.

He did most of his damage with the Reds at home, though, in what has traditionally been a great hitters' park—.298 AVG, .561 SLG and 12 HR at Great American Ballpark—and was not anywhere near as impactful after getting traded to San Diego.

Will a team that's desperate at either third base or second base (perhaps the White Sox, Orioles or Mariners) overlook some of those details and give Drury even more than the two-year, $13 million deal that Spotrac suggests is his market value?

How much might that market value go up if he has some big moments in the NLCS and/or World Series?

And will it be a home run of an acquisition or will they live to regret the move?

A Quartet of High-Priced, Middle-Aged Relief Pitchers

ARLINGTON, TX - OCTOBER 4: Aroldis Chapman #54 of the New York Yankees pitches against the Texas Rangers during the seventh inning in game one of a double header at Globe Life Field on October 4, 2022 in Arlington, Texas. (Photo by Ron Jenkins/Getty Images)
ARLINGTON, TX - OCTOBER 4: Aroldis Chapman #54 of the New York Yankees pitches against the Texas Rangers during the seventh inning in game one of a double header at Globe Life Field on October 4, 2022 in Arlington, Texas. (Photo by Ron Jenkins/Getty Images)

Aroldis Chapman ($18 million in 2022; 36.1 IP, 9 saves, 4.46 ERA, 10.7 K/9, 1.5 K/BB)
Craig Kimbrel ($16 million in 2022; 60.0 IP, 22 saves, 3.75 ERA, 10.8 K/9, 2.6 K/BB)
Kenley Jansen ($16 million in 2022; 64.0 IP, 41 saves, 3.38 ERA, 12.0 K/9, 3.9 K/BB)
Zack Britton ($14 million in 2022; 0.2 IP, 13.50 ERA, 13.5 K/9, 0.2 K/BB)


Each of these four formerly elite closers will be at least 35 years old by the end of May.

Each one is also an unrestricted free agent after a 2022 campaign spent making at least $14 million for a team that won at least 99 games.

The biggest risk of the bunch is, unquestionably, Britton.

He missed most of 2021 after undergoing arthroscopic surgery on his elbow during spring training, and then Tommy John surgery in September caused him to miss the rest of that season and nearly all of 2022. But he had a 1.90 ERA between 2019-20, this after a sensational run with Baltimore from 2014-16. Maybe he can bounce back?

The other three each had their moments in 2022—stretches in which it looked like they were worth eight figures as well as runs in which the thought of allowing them to pitch in one more high-leverage situation was downright nauseating.

Will any of them be good enough to play a pivotal role in a bullpen in 2023?

If so, which one(s)?

If they want to pitch for multiple more seasons, all four will probably end up getting two-year deals somewhere, with Jansen presumably getting the most money in light of his NL-best save total. But it will be interesting to see where the dollar amounts land.

Aaron Judge, CF/RF, New York Yankees

CLEVELAND, OHIO - OCTOBER 16: Aaron Judge #99 of the New York Yankees looks on prior to playing the Cleveland Guardians in game four of the American League Division Series at Progressive Field on October 16, 2022 in Cleveland, Ohio. (Photo by Christian Petersen/Getty Images)
CLEVELAND, OHIO - OCTOBER 16: Aaron Judge #99 of the New York Yankees looks on prior to playing the Cleveland Guardians in game four of the American League Division Series at Progressive Field on October 16, 2022 in Cleveland, Ohio. (Photo by Christian Petersen/Getty Images)

2022 Salary: $19 million

2022 Stats: .311/.425/.686, 62 HR, 131 RBI, 16 SB

Let's not allow the 62 home runs and the darn near Triple Crown to make us forget how the Yankees and Aaron Judge got to this point in the first place.

They reportedly offered Judge a seven-year, $213.5 million extension this past offseason. That equates to $30.5 million per year—an inconceivable amount of money to us normal folk, but not even a top-10 average salary in baseball.

Judge wanted more because of what he can do on the field.

The Yankees were unwilling to go any higher, presumably because of the amount of time in recent years that Judge spent unable to get onto the field.

Judge hit 52 home runs as a rookie in 2017, leading the AL in runs, home runs and walks (and strikeouts) en route to AL ROY and a second-place finish for AL MVP. But he missed 30.9 percent of games in 2018, 37.0 percent of games in 2019 and 53.3 percent of games in 2020.

There was a shoulder surgery, a wrist fracture, a couple of oblique strains, a cracked rib, a collapsed lung and a calf strain as he understandably got the "injury prone" label. And despite playing in 94.1 percent of games over the past two seasons, there's still an inherent fear that committing to seven (or more) years of paying Judge $40 million (or more) per season could be a team-crippling disaster.

He's going to get that money, probably from the Yankees. Wherever he lands, the fans will be euphoric. But there will be some concern about what the contract ends up boiling down to on a per-game level by the time it's finished.

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