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Putting a price tag on extending Kyle Tucker, Dylan Cease and other looming free agents

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Putting a price tag on extending Kyle Tucker, Dylan Cease and other looming free agents

Monday’s deep dive into Paul Skenes, perhaps the most interesting extension case in baseball, was a sneak peek of Extension Week.

Now I’ll start a broader look at potential extension candidates, concentrating today on players whose value is less speculative: impending free agents.

These players are, in general, less likely to sign an extension with free agency waiting at the end of this season, and my analysis here is basically projecting what each player could earn on the open market before adding in his 2025 salary. If nothing else, it’s an early projection for a free-agent deal this upcoming winter.

Since last spring’s Extension Week, three players actually put pen to paper on an extension, all earning a bit more than I projected:

Player Projected Received

4 years, $136M

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3 years, $126M

5 years, $82.5M

10 years, $122.4M

6 years, $48M

6 years, $55M

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*Here and in all other tables, I’ll account for significant deferrals by using the present-day value of the contract when it was signed.

I’ve tried to factor that into the analysis this year.

Here’s how I go about this: I’ve got a big Excel spreadsheet with more than 1,100 free-agent and extension contracts in it, as well as players’ performance in the years leading up to those contracts, as defined by FanGraphs’ wins above replacement. Whereas players get paid off home runs and saves in arbitration, I’ve found fWAR to be a solid (though not all-knowing) predictor of earnings on the open market.

I plug extension candidates into the spreadsheet, find players with similar levels of production (and ideally with similar amounts of team control left) before they signed their deals, and work off of those comps.

A few overall points worth remembering:

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  • For extensions, team control is important. If Player A looks just like Player B, except Player A has three years of arbitration ahead of him and Player B was a free agent, Player A isn’t going to get the contract Player B did. However, what Player B made in free agency is still useful as a guide to what the later part of Player A’s contract can look like.
  • For starting pitchers and position players, I look at fWAR in one-, three- and five-year samples, with a special emphasis on the shorter term. For extensions in particular, the five-year sample is less helpful because a lot of players haven’t been playing for five full years.
  • For relievers, I look at one- and two-year samples. What happened five years ago isn’t really relevant for such a volatile position, and I’ve found more of a recency bias in contracts here than elsewhere.
  • This is an exercise in player valuation, not commentary on the likelihood of an extension being signed or whether I think a team or player should sign an extension at the value I suggest. I find doing this helpful even when an extension is unlikely because it helps me understand what the market may be once a player reaches free agency or to see how the player’s value has changed over time.

As we go through this, keep in mind:

  • The actual extension projection in all cases includes what the player is slated to make this season. It will likely contain a lower AAV (average annual value) than the player would get on the open market for this reason.
  • These players should have higher projections this year than last year. Last year, they were two years removed from free agency, and they were slated to make below market value via arbitration.
  • The number in parentheses is the player’s age on July 1 of this year.
  • In the charts, “Today AAV” is the average annual value of the deal adjusted for inflation.

Vladimir Guerrero Jr. (26)

Maybe no one in baseball had a better year for their potential earnings than Guerrero. His 5.5-win season (according to FanGraphs) washed away any concerns after a pedestrian 2023 and reminded the sport that he’s one of its very best hitters. Plus, a player with similar strengths and weaknesses signed for more than $750 million. So Guerrero is in significantly better shape this spring than he was last spring.

Earlier in spring training, I broke down why Guerrero’s value in an extension has proven difficult to pin down. At the moment, he looks like he belongs just below the second tier of free-agent contracts for first basemen (Miguel Cabrera is the sole occupant of the top tier).

Player

  

Signed

  

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Ages

  

fWAR1

  

fWAR3

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fWAR5

  

Years

  

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Total

  

Today AAV

  

2012

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32-41

3.9

19.1

35.5

10

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240

33.6

2014

30-39

6.4

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17.9

21.4

10

225

30.6

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2019

31-35

5.2

15.4

26.9

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5

130

32.8

2009

29-36

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6.9

14.8

24.9

8

180

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33.8

2025

26

5.5

10.1

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16.7

Extending a deal for a massive 14 free-agent years would limit the AAV just a touch, to about $30 million. I know, I know: A deal that long comes off as crazy. But there have been a dozen players who have signed deals at least nine years in length in the last three offseasons — or just shy of the number of contracts that long that were signed over the prior decade. Four of them (Juan Soto, Trea Turner, Manny Machado and Xander Bogaerts) extend through a player’s age-40 season, as this one would for Guerrero.

2024 extension projection: Seven years, $185 million
2025 Salary:
$28.5 million
2025 extension projection:
15 years, $450 million


Kyle Tucker (28)

If Tucker had remained healthy last season and continued playing the way he did in the first half of the season, his best statistical comp would be… Soto. Because of his age, Tucker wouldn’t have been able to get as long a deal as Soto, but he would have been able to make a case for a similar average annual value.

The comps are not bad as is.

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Player

  

Signed

  

Ages

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fWAR1

  

fWAR3

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fWAR5

  

Years

  

Total

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Today AAV

  

2019

26-35

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6.2

14.9

23.8

10

300.0

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37.8

2009

29-36

6.9

14.8

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24.9

8

180.0

33.8

2025

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28

4.2

14.1

22.9

2025

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31-33

4.1

14.0

20.5

3

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90.0

30.0

2012

28-36

4.7

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13.2

19.2

9

214.0

33.3

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Tucker should be able to secure a deal through at least his age-36 season, and it’s not hard for him to argue he should go longer than either Teixeira or Fielder. Let’s go with 10 years at about $35 million each before adding in this season’s salary.

2024 extension projection: Eight years, $204 million
2025 salary:
$16.5 million
2025 extension projection:
11 years, $366 million


Dylan Cease (29)

Last season, Cease and Zac Gallen entered in a similar spot: at the same age, earning about the same in arbitration, in line for about the same extension. Then, while Gallen had a nice season, Cease posted another top-five finish in the Cy Young balloting. He’s placed himself in the same group as the top earning starters from this past winter.

Player

  

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Signed

  

Ages

  

fWAR1

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fWAR3

fWAR5

  

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Years

  

Total

  

Today AAV

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2025

29

4.8

12.8

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17.8

2025

30-35

3.7

11.8

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24.2

6

193.8

32.3

2015

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31-36

5.6

11.6

19.1

6

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155.0

35.1

2025

31-38

3.4

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10.1

17.6

8

218.0

27.3

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Lester sets the high end for Cease, and that comp suggests Cease can in fact get more than Burnes just did from the Diamondbacks. Both point to a deal buying out six free-agent years. Let’s estimate those at just under $33 million and add in this year’s salary.

2024 extension projection: Seven years, $140 million
2025 salary:
$13.75 million
2025 extension projection:
Seven years, $210 million


Zac Gallen (29)

Right now, Gallen isn’t quite on the same level as Cease.

Player

  

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Signed

  

Ages

  

fWAR1

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fWAR3

  

fWAR5

  

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Years

  

Total

  

Today AAV

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2016

30-35

4.0

9.4

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17.0

6

130.0

29.0

2016

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30-34

3.0

12.0

18.7

5

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110.0

29.5

2025

29

2.8

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12.2

15.6

This sets him up for roughly the 2025 version of Cueto’s deal in free agency: six years and $174 million, before adding this year’s salary.

2024 extension projection: Seven years, $140 million
2025 salary:
$13.5 million
2025 extension projection: Seven years, $187 million


Framber Valdez (31)

Valdez has had just as much success as Cease and Gallen; the issue for him is he’s two years older than those guys. Starters who hit the open market entering their age-32 season seldom sign for more than three or four years. (The exceptions are guys like Zack Greinke, CC Sabathia and Cliff Lee, who all owned Cy Young awards.)

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Player

  

Signed

  

Ages

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fWAR1

  

fWAR3

  

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fWAR5

  

Years

  

Total

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Today AAV

  

2016

30-35

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4.0

9.4

17.0

6

130.0

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29.0

2016

30-34

3.0

12.0

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18.7

5

110.0

29.5

2025

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31

3.6

12.4

16.8

Let’s stick with the same comps as Gallen but only for four free-agent years rather than six.

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2024 extension projection: Five years, $105 million
2025 salary:
$18 million
2025 extension projection:
Five years, $134 million


Devin Williams (30)

Just looking at the raw numbers isn’t charitable to Williams, who on a per-appearance basis is right there with recent closers who signed four-year deals like Raisel Iglesias and Tanner Scott. (Williams missed roughly two-thirds of last season.)

Player

  

Signed

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Ages

  

fWAR1

  

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fWAR2

  

Years

  

Total

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Today AAV

  

2022

32-35

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2.0

5.0

4.0

58

16.4

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2025

30

1.6

4.5

4.0

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72.0

18.0

2025

30

0.8

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2.6

Given that no position gets paid on reputation quite the way closer does, Williams could still be in line for a deal that rivals Scott’s, before adding in this year’s salary.

2024 extension projection: N/A
2025 salary:
$8.6 million
2025 extension projection:
Five years, $80 million

(Top photo of Dylan Cease: Orlando Ramirez / Getty Images)

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Keith Olbermann under fire for calling Lou Holtz a ‘scumbag’ after legendary coach’s death

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Keith Olbermann under fire for calling Lou Holtz a ‘scumbag’ after legendary coach’s death

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Former ESPN broadcaster Keith Olbermann once again incited backlash on social media Wednesday after he called late legendary college football coach Lou Holtz a “legendary scumbag” in an X post on the day Holtz was announced dead. 

“Legendary scumbag, yes,” Olbermann wrote in response to a clip of Holtz criticizing former President Joe Biden in 2020 for supporting abortion rights. 

Olbermann received scathing criticism in response to his post on X.

 

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“You’re a scumbag that needs mental help,” one X user wrote to Olbermann. 

One user echoed that sentiment, writing to Olbermann, “You’re the real scumbag here. Lou Holtz had more class, integrity, and genuine decency in his pinky finger than you’ll ever show in your lifetime.”

Another user wrote, “You’re a grumpy, lonely, Godless man. All the things Lou Holtz was not.”

Keith Olbermann speaks onstage during the Olbermann panel at the ESPN portion of the 2013 Summer Television Critics Association tour at the Beverly Hilton Hotel July 24, 2013, in Beverly Hills, Calif.  (Frederick M. Brown/Getty Images)

Olbermann has made it a pattern of sharing politically charged far-left statements that are often combative and ridiculed on social media, typically resulting in immense backlash.

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After the U.S. men’s hockey team’s gold medal win, Olbermann heavily criticized the team for accepting an invitation from President Trump to the State of the Union address. Olbermann wrote on X that any members of the men’s team who attended the event were “declaring their indelible stupidity and misogyny,” while praising the women’s team for declining the invitation.

In January, Olbermann attacked former University of Kentucky women’s swimmer Kaitlynn Wheeler for celebrating a women’s rights rally outside the U.S. Supreme Court during oral arguments for two cases focused on the legality of biological male trans athletes in women’s sports.

Former Notre Dame football coach Lou Holtz listens before being presented with the Presidential Medal of Freedom at the White House in Washington, D.C., Dec, 3, 2020.  (Doug Mills/The New York Times/Bloomberg via Getty Images)

“It’s still about you trying to find an excuse for a lifetime wasted trying to succeed in sports without talent,” Olbermann wrote in response to Wheeler’s post. 

In 2025, Olbermann faced significant backlash after posting (and later deleting) a message on X aimed at CNN contributor Scott Jennings, that said, “You’re next motherf—–,” shortly after the assassination of conservative influencer Charlie Kirk. 

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Holtz was a stern supporter of President Donald Trump, even saying in February 2024 that Trump needed to “coach America back to greatness!”

Near the end of Trump’s first term, shortly after former President Joe Biden defeated him in the 2020 election, Trump awarded Holtz with the Presidential Medal of Freedom, the highest civilian award of the United States. 

After Holtz’s death was announced Wednesday, several top GOP figures paid tribute to the coach on social media. 

Those GOP lawmakers included senators Tommy Tuberville, R-Ala.; Todd Young, R-Ind.; Tom Cotton, R-Ark.; and Lindsey Graham, R-S.C.; representatives Greg Murphy, R-N.C.; David Rouzer, R-N.C.; Erin Houchin, R-Ind.; and Steve Womack, R-Ark.; and Florida Gov. Ron DeSantis; Indiana Gov. Mike Braun; U.S. Education Secretary Linda McMahon; and Rudy Giuliani.

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Lou Holtz, former Notre Dame football coach, addresses the America First Policy Institute’s America First Agenda Summit at the Marriott Marquis July 26, 2022. (Tom Williams/CQ-Roll Call, Inc)

At the time of publication, prominent Democrat leaders have appeared silent on Holtz’s passing, including prominent Democrats with a football background. 

Minnesota Gov. Tim Walz, who worked as an assistant high school football coach; Sen. Cory Booker, D-N.J., who was a recruiting target for Holtz in 1986 as a college prospect; Rep. Colin Allred, D-Texas, who played in the NFL; and Rep. Kam Buckner, D-Ill., who played football for the University of Illinois, have not posted acknowledging Holtz’s death. 

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Stephen A. Smith called Zion Williamson a ‘food addict,’ is now feuding with the Pelicans on social

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Stephen A. Smith called Zion Williamson a ‘food addict,’ is now feuding with the Pelicans on social
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Williamson has been listed as 6-foot-6, 284 pounds since New Orleans selected him out of Duke with the No. 1 overall pick in the 2019 draft. His weight and fitness level have been regularly criticized, and the amount of time Williamson has missed because of injuries hasn’t helped (including all of the 2021-22 season following offseason right foot surgery).

After playing only 30 games last season because of a left hamstring strain and a lower back injury, Williamson reported for 2025-26 looking trim and in shape. He told reporters that he and Pelicans trainer Daniel Bove had come up with a strategy to address his fitness while rehabbing his hamstring and that he stuck to it.

“I haven’t felt like this since college, high school,” Williamson said at the time, “where I can walk in the gym and I’m like just, ‘I feel good.’”

Williamson has played in 46 of the Pelicans’ 63 games this season, already the third-most games he has played in his seven NBA seasons. In a recent interview with ESPN’s Malika Andrews, Williamson addressed how the past criticism affected him mentally.

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“I would say the most difficult point was when I missed my third year with a broken foot, and there was a lot of criticism on my weight, my care for the game, etc.,” Williamson said. “But … while people were saying what they’re saying — and everybody’s entitled to their own opinion, it is what it is — I’m in Portland rehabbing, not knowing if my foot’s gonna heal, and it was frustrating. It was very frustrating.

“I was low. I was really low because I just wanted to play basketball. I just wanted to play the game I love, but every time you turn the TV on, every time I check my phone, it was nothing but negative criticism, man. At the time, it did a lot, like I said, it did a lot, but it was a blessing in disguise, and I learned from it and I grew from it.”

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ESPN analyst Paul Finebaum questions Trump’s college sports reform meeting as potential ‘circus’

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ESPN analyst Paul Finebaum questions Trump’s college sports reform meeting as potential ‘circus’

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President Donald Trump will host a White House roundtable regarding college athletics reform later this week.

The panel is expected to include prominent coaches, college sports and pro sports league commissioners, and other professional athletes, according to OutKick.

The group will meet March 6 to examine solutions to key challenges, including NCAA authority; name, image and likeness issues (NIL); collective bargaining; and governance concerns. 

 

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President Donald Trump holds a football presented to him during a ceremony to present the Commander-in-Chief’s Trophy to the US Naval Academy football team, the Navy Midshipmen, in the East Room of the White House on April 15, 2025 in Washington, D.C. (BRENDAN SMIALOWSKI/AFP via Getty Images)

The meeting Friday will include big names like Nick Saban, Urban Meyer, Adam Silver and Tiger Woods. Trump has been adamant about “saving college sports,” even signing an executive order setting new restrictions on payments to college athletes back in July.

However, ESPN college analyst Paul Finebaum, who has previously hinted at a congressional run as a Republican, remains a bit skeptical.

“The easiest thing, guys, is just to say this is ridiculous,” Finebaum said to Greg McElroy and Cole Cubelic on WJOX. “And I read the other day, ‘Why is Nick Saban going?’ Why is anybody going? The bottom line is this. If something doesn’t happen very quickly, and I mean in the next short period of time, we’re talking about weeks, not years, then this thing could blow up.

“However it came about, I’m in favor of. The question now becomes, with some of the most powerful people in Washington in the same room, including the most powerful person in the country, can anything get done, or will it be a circus? Will it be just another show?”

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U.S. President Donald Trump shakes hands with former Alabama Crimson Tide football coach Nick Saban as Trump takes the stage to address graduating students at Coleman Coliseum at the University of Alabama on May 01, 2025 in Tuscaloosa, Alabama. (Anna Moneymaker/Getty Images)

Trump’s order prohibits athletes from receiving pay-to-play payments from third-party sources. However, the order did not impose any restrictions on NIL payments to college athletes by third-party sources.

A House vote on the SCORE Act (Student Compensation and Opportunity through Rights and Endorsements), which would regulate name, image, and likeness deals, was canceled shortly before it was set to be brought to the floor in December.

The White House endorsed the act, but three Republicans, Byron Donalds, Fla., Scott Perry, Pa., and Chip Roy, Texas, voted with Democrats not to bring the act to the floor. Democrats have largely opposed the bill, urging members of the House to vote “no.”

President Donald Trump looks on before the college football game between the US Army and Navy at the M&T Bank Stadium in Baltimore, Maryland, on Dec. 13, 2025.  (Alex WROBLEWSKI / AFP via Getty Images)

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The SCORE Act would give the NCAA a limited antitrust exemption in hopes of protecting the NCAA from potential lawsuits over eligibility rules and would prohibit athletes from becoming employees of their schools. It prohibits schools from using student fees to fund NIL payments.

Fox News’ Chantz Martin and Ryan Gaydos contributed to this report.

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