Upcoming MLB Free Agents Who Need a Strong Finish in 2023 to Cash in

Over the course of Major League Baseball's last two offseasons, more than $7 billion worth of contracts were handed out to free agents, with 20 players agreeing to deals worth at least $100 million.

This year's crop of more than 200 impending free agents would love to get a slice of that sweet, sweet cash.

However, there are quite a few players who need to prove over these final few weeks of the regular season that they are worthy of a hefty investment.

In several cases, we're talking about guys who missed most or all of last season and are just looking to show to prospective teams that they can stay healthy.

But for the most part, we'll be looking at players who have struggled as of late (or as of the entire season) and need a strong finish to remind everyone what they can bring to the table.

Players are listed in alphabetical order by last name. Statistics are current through the start of play Friday, unless otherwise noted.

2023 Stats: .239/.282/.296, 1 HR, 24 RBI, 13 SB, -1.8 bWAR

We get things started with a slightly complicated contract situation, as the White Sox have a $14 million club option for Tim Anderson for next season.

If he's too good down the stretch, they'll simply hang onto him for another year. But if he doesn't rally, they could pay the $1 million buyout and let some other team take a gamble on the oft-injured shortstop whose power at the plate has been steadily vanishing over the past three seasons.

For a hot minute there in late July, it looked like Anderson had finally figured things out. He entered the All-Star Break hitting a preposterously bad .223/.259/.263. But in his first 14 games of the second half, he hit .351, including his lone home run of the season.

Since July 30, though, he has fallen right back apart, batting .221 and striking out in 33 of 101 trips to the plate.

Anderson has always been a bit strikeout prone, but it's like he can't even see the ball lately. There was a stretch of 16 consecutive games in August in which he struck out at least once.

All that said, we're talking about a guy who hit .318 from 2019-22, including winning a batting title. If he catches fire over the final few weeks of the regular season, that could be all the evidence teams need to believe he's ready for a bounce back in 2024.

2023 Stats: .251/.343/.405, 15 HR, 55 RBI, 0.8 bWAR

For Michael Conforto, 2023 was always about proving to Major League Baseball that he's back.

He missed all of 2022 with a shoulder injury after struggling through a down year in 2021, but he had a bWAR of 12.2 from 2017-20 and reasonably could have gotten a $100 million contract if he had hit free agency three years ago.

He took a one-year, $18 million deal (with a player option for a second $18 million season) from San Francisco, planning on hitting 30 or so home runs before declining that option and making some big bucks on a long-term contract.

Early in the year, he was certainly trending in that direction. Through June 8 (53 games), Conforto was hitting .251/.352/.469 with 12 home runs and 31 RBI, putting him on a 162-game pace of 37 homers with 95 runs driven in.

In 58 games played since then, though, he has hit just three home runs, slugging a meager .346.

He was starting to heat up in mid-August, however, he landed on the IL with a hamstring strain two weeks ago.

But if he can come back soon and become the offensive leader that San Francisco has been lacking all season, it could be what propels the Giants into the postseason and it could net him the big contract he was seeking in each of the past two offseasons.

2023 Stats: 134.0 IP, 4.84 ERA, 1.55 WHIP, 9.1 K/9, 1.0 bWAR

Back in 2018 and 2019, Jack Flaherty was sensational. He made 61 starts with a 3.01 ERA and a 10.7 K/9. He got NL Rookie of the Year votes in 2018, as well as Cy Young and MVP votes in 2019.

The past two seasons have been a much different story, making 34 appearances with a 4.71 ERA and an 8.9 K/9.

But at least he has been mostly healthy this season. And it looked as if he had rallied from a brutal, walk-infested start to the year. In six starts from July 1 through August 3, he had a 2.78 ERA. When he was traded from St. Louis to Baltimore, it was plausible he would become the ace of the O's staff.

Over his last four starts, however, that ERA has tripled to 8.35, as he allowed as many home runs in those four starts as he did in the previous 13 combined.

Could he flip the switch again?

And how lucrative would it be if Flaherty spins a gem during the colossal showdown with Tampa Bay next weekend before also making a few solid appearances in the postseason?

After all, we're talking about a pitcher who doesn't even turn 28 for another few months, and one who has struck out nearly 27 percent of batters faced in his career.

If he had been impressive all season long, Flaherty could have emerged as one of the biggest names in this year's free agent market. But if he finishes with a flourish, maybe he could still get a Kodai Senga type of deal (five years, $75 million).

2023 Stats: .177/.301/.440, 21 HR, 40 RBI, 0.5 bWAR

At this point, you pretty well know what you're getting from Joey Gallo: a ton of strikeouts, a terrible batting average and just enough home runs to make things interesting.

Dating back to the start of 2017, Gallo is pretty much neck-and-neck with Mike Trout in terms of plate appearances and home runs—Trout has 200 in 2,963 trips to the plate; Gallo has 191 in 2,990 trips to the plate.

Of course, the similarities stop there, as Gallo has a .198 batting average during that seven-season window.

There was hope that the elimination of the shift heading into this season would provide a little jolt to Gallo's dreadful BABIP. However, it hasn't changed in the slightest, and he's now striking out at an even higher rate than he did in any of the past six years.

Yet, teams keep giving him all of the opportunities to whiff.

In the span of 17 months, he went from the Rangers to the Yankees to the Dodgers to the Twins. And it's inevitable that one of the many poor-slugging teams—Cleveland, Detroit, Milwaukee or Washington to name a few—will take a flyer on Gallo this offseason.

The price of that flyer and whether there's a second season attached to it will depend on how well he clubs the ball down the stretch.

From August 13 through September 3, Gallo went 1-for-25 with 16 strikeouts. But if he can put together one of his hot streaks and hit five or six home runs the rest of the way—and maybe crush one in the postseason?—it would get noticed.

2023 Stats: 156.2 IP, 4.88 ERA, 1.32 WHIP, 9.7 K/9, 1.8 bWAR

Two months ago, the idea of Lucas Giolito needing to prove anything in September would have been laughable.

Through his first 19 starts of this season, Giolito had a 3.45 ERA, including twice tossing six no-hit innings. He entered the year as easily one of the top free-agents-to-be not named Shohei Ohtani, and by mid-July was viewed by most as the biggest name on the trade block.

And then the wheels came off.

In one of his final starts with the White Sox, Giolito was shelled by the Mets for eight earned runs with three homers allowed. In his second start with the Angels, Atlanta lit him up for nine earned runs and three more home runs. And in his Guardians debut in a must-win game against Minnesota, another nine earned runs and three more home runs.

All told, he has been obliterated to the tune of an 8.53 ERA over his last nine appearances, allowing an outlandish 16 home runs in 44.1 innings of work.

At this point, teams have to wonder if they'd be getting the annual Cy Young candidate from 2019-21 who posted a 3.47 ERA and an 11.1 K/9, or if they'd be getting the version of Giolito that allowed more earned runs and walks than any other AL pitcher in 2018, that sputtered to a 4.90 ERA last year and that has been a disaster since the All-Star Break.

As the rotation currently stands, Giolito's next three starts will come against the Angels, the Rangers and the Orioles. That's a stretch against which a rough finish easily could get even worse. But if he can stifle Texas' bats, it would be worth adding to his resume in free agency.

2023 Stats: 121.1 IP, 3.49 ERA, 1.19 WHIP, 8.7 K/9, 1.6 bWAR

Most of the free agents on this list are hoping to salvage what has been to some extent a disappointing season.

In Seth Lugo's case, a strong September would go a long way toward proving he has the endurance to be a regular in the rotation for at least a few more years.

Prior to this season, Lugo had spent the majority of the past half-decade as a middle reliever with the Mets, never logging more than 101.1 innings in an MLB season.

Between 2021 and 2022, he made 108 appearances, never going more than 2.0 innings in any of them.

When he hit free agency last offseason, he wanted to reprise his role as a starting pitcher. However, no one was particularly eager to invest in him doing so successfully. He got a one-year, $7.5 million deal (with some incentives for games started/total appearances) from San Diego with a player option in the same amount for 2024.

But after making 12 total starts from 2018-22, Lugo has logged 14 quality starts for the Padres—allowing two or fewer earned runs in each of them, no less.

He did miss a little over a month with a calf strain, but the increased workload doesn't appear to have had any adverse effect on his pitching arm/shoulder. In fact, Lugo has pitched at least into the sixth inning in 11 of his last 13 starts, including going six scoreless innings in three of his last four outings.

If he can make it another four weeks—likely four more starts, based on San Diego's rotation and remaining schedule—without any issues, you better believe Lugo is headed for way more than $7.5 million when he jumps back into the free agency pool. Spotrac puts Lugo's market value at three years, $29.5 million, but that's probably even a bit low, considering Ross Stripling got a two-year, $25 million deal last winter.

2023 Stats: 96.0 IP, 4.50 ERA, 1.31 WHIP, 9.5 K/9, 1.1 bWAR

After missing all but 1.1 innings of 2021 and the entirety of 2022 while recovering from Tommy John surgery, James Paxton finally made it back to a big league mound in mid-May, going roughly 765 days between appearances.

You wouldn't know it from how well he pitched early on, though.

Through his first nine starts, Paxton had a 2.70 ERA and a K/9 ratio of 11.0.

After 16 starts, he was still sitting at strong marks of 3.34 and 9.7, respectively, and had registered a quality start in 50 percent of his appearances.

Even though he turns 35 in November and is currently playing on a $4 million salary, it seemed the veteran Canadian southpaw could be headed for a nice little payday on a one-year or maybe two-year contract.

Paxton has fallen on hard times as of late, though, shelled for 16 earned runs over his last 9.2 innings of work—the worst of which came against the lowly Kansas City Royals, who scored a season-high 13 runs in that game started by Paxton.

Just a little rough patch late in an otherwise solid campaign, or is something more sinister afoot for a pitcher who has battled more than his fair share of injuries over the past decade?

How Paxton fares over his final few turns through the rotation could answer that question and dictate his value in free agency.

2023 Stats: .262/.303/.379, 6 HR, 56 RBI, 13 SB, 0.4 bWAR

Amed Rosario entered 2023 as one of the most coveted impending free agents. In late February, CBS Sports had him at No. 5 in its ranking of the top players destined for the open market, behind only Shohei Ohtani, Julio Urias, Aaron Nola and Matt Chapman.

After batting .282 with 41 home runs and 50 stolen bases from 2019-22, really all this 27-year-old shortstop had to do to strike it rich this offseason was keep the status quo. Because after a 2022-23 class featuring Trea Turner, Xander Bogaerts, Carlos Correa and Dansby Swanson, this year's crop of middle infielders hitting free agency is mighty bleak.

But for the first third of this season, Rosario's walk year was a disaster. Through 52 games, he was hitting .224/.270/.314 with just one home run. (He didn't hit his second dinger until his 78th game on July 4.)

The second third of his season went much better, batting .304 while operating at a 162-game pace (for 55 games) of 194 hits and 112 RBI. However, Rosario is languishing once again, batting .213 with no homers and just five RBI over his last 19 games.

Even if he continues to hit like that for a few more weeks and ends the year at more or less the Wins Above Replacement break-even point, there's still going to be somewhat of a bidding war for his services, as the only other somewhat noteworthy shortstop out there this year is Isiah Kiner-Falefa (assuming Javier Báez does not opt out of the remaining four years and $98 million on his contract with Detroit).

But whether he's worth eight figures on an annual basis over the course of a three-year or four-year deal may be determined by how well he hits the rest of the way.

2023 Stats: 34.0 IP, 2.65 ERA, 1.06 WHIP, 7.4 K/9, 0.3 bWAR

After undergoing the second Tommy John surgery of his career last June, Hyun-Jin Ryu missed most of 2022 and the first two-thirds of this season.

Considering he also struggled in 2021, there were reasonable concerns that the 36-year-old southpaw would never again come close to matching his level of success from 2018-20, when he made 56 starts with a 2.30 ERA, twice finishing top three in the Cy Young vote.

Lo and behold, Ryu has been surprisingly solid in his return to the mound.

He took a comebacker off the inside of his right knee in his second start, leaving that game after four innings with a no-hitter intact. He didn't miss any time, though, going five innings without allowing an earned run six days later against the Cubs.

It seems five innings is his new normal, though, going exactly that distance in six of his seven starts.

I can appreciate that the Blue Jays are limiting his pitch count as he regains his stamina, but if that continues to be the case for the rest of the season, it's going to be difficult to view Ryu as anything more than a No. 5 starter in the forthcoming free agency negotiations.

Conversely, if he can go 6+ innings in any of his remaining starts against Texas, Boston, Tampa Bay and New York, that's going to resonate.

A guaranteed multi-year contract is unlikely, but Corey Kluber and Johnny Cueto were the same age last offseason as Ryu will be this offseason, and they got one-year deals (with club options for a second season) for $10 million and $8.5 million, respectively.

Granted, Kluber and Cueto have both been ineffective in 2023 and may have slightly ruined Ryu's market. But with a strong finish, I could easily see Ryu getting a one-year, $12 million deal with some incentives for games started and/or an option for a second year.

2023 Stats: .164/.238/.239, 3 HR, 22 RBI, 1 SB, negative-1.3 bWAR

Kolten Wong was seemingly on a one-man mission to destroy the Seattle Mariners.

After batting .262/.337/.439 with 29 home runs and 29 stolen bases between 2021 and 2022 in Milwaukee, Wong couldn't hit the broad side of a barn in Seattle, going from a .262 hitter to a .227 slugger. It wasn't until they stopped playing him and eventually released him that the Mariners finally went on a tear.

But Wong later signed a minor-league deal with the Dodgers and hit .539 in three games at Triple-A before getting called up and smashing a pinch-hit, three-run homer in his first AB in LA.

Surely, the Dodgers would love for Wong to be the answer to their problem at second base, as life-long outfielder Mookie Betts has started 14 of the last 19 games in the infield while primary left fielder David Peralta has hit .250 with nary a homer since the All-Star Break. But they're not exactly eager to throw Wong into the deep end of the pool, only letting him start one game thus far.

If he can prove himself in that role, though, maybe there are a few more chapters to be written on a career that looked like it might be finished a month ago. Goodness knows there is always a need for second basemen who can provide any sort of value at the dish.