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Front Office Sports - The Memo

Afternoon Edition

May 23, 2025

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Paul Skenes is already one of MLB’s biggest stars, but as the Pirates continue to struggle, trade chatter around him is getting louder. A blockbuster deal could reshape the franchise—or haunt it for years.

—Eric Fisher, Colin Salao, and David Rumsey

Paul Skenes Blockbuster Trade Buzz Is Building. Will the Pirates Cash In?

Charles LeClaire-Imagn Images

Just a year into the big league career of Paul Skenes, the star Pirates pitcher is already the subject of fast-growing trade talk. While the club is steadfastly denying it, the ongoing chatter shows the massive surplus value Skenes offers Pittsburgh—or any other franchise.

Skenes hit the first anniversary of his promotion to the Pirates earlier this month, and in those 12 months, he has started an All-Star Game, won a Rookie of the Year Award, been a Cy Young Award finalist, and firmly established himself as one of MLB’s biggest stars. A 3–5 record so far this year is much more reflective of the Pirates’ ongoing struggles, as Skenes has been nearly as dominant on the mound as he was in 2024. 

The pitcher, however, is set to earn just $875,000 this year, a mere fraction of frontline MLB starting-pitcher salaries that now frequently exceed $25 million. Skenes won’t become arbitration-eligible until 2027, and his free agency will wait until after the 2029 season. Because of all that, the Pirates could conceivably garner an unprecedented trade haul. 

In 2022, the Nationals traded Juan Soto, then under club control through the 2024 season, to the Padres for a massive package that included six players going to Washington, including current cornerstone players James Wood and MacKenzie Gore. That deal—considered in some circles as baseball’s equivalent to the famed Herschel Walker trade in football in 1989 that set up the Cowboys’ dynasty the following decade—represents a baseline level for a Skenes deal. Given Skenes is about to turn just 23 and the scarcity of dominant starting pitchers across the league, the Pirates would be able to demand much more.

Pirates GM Ben Cherington, however, said no such deal is in the works.

“It’s not at all part of the conversation,” Cherington said Thursday. 

Pressure on Cherington and Pirates owner Bob Nutting will only grow in the weeks leading up to the July 31 trade deadline to use Skenes to reshape a long-struggling franchise. The Pirates have just four winning seasons in the last 33 years and are again languishing in last place in the National League Central division.

Worse yet, there’s little immediate hope of a turnaround as the team has little in the way of impact position players, either in Pittsburgh or in the farm system. The Pirates’ offense currently is last or next to last in MLB in nearly every major category. Off the field, it’s been much the same story as the club has faced a series of controversies, such as the commemorative PNC Park “Bucco Bricks” ending up at a recycling facility and a sign inside the ballpark honoring the late franchise icon Roberto Clemente getting replaced by an alcohol advertisement.

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Maple Leafs Cut Ties With President As Cup Drought Nears Six Decades

John E. Sokolowski-Imagn Images

The Maple Leafs, the NHL’s most valuable franchise and essentially the Yankees or Cowboys of Canadian pro sports, are once more searching for answers after another early playoff exit has led to the dismissal of team president and alternate governor Brendan Shanahan. 

The team, worth an estimated $3.8 billion, said Thursday it would not renew Shanahan’s contract after 11 years at the helm. During that run, the Toronto native and former Red Wings star led the Maple Leafs to nine playoff appearances as he implemented a broad-based reorganization dubbed the “Shanaplan.”

The team, however, under his leadership, never advanced beyond the second round of the postseason. That continued this year as the Maple Leafs, after winning a “Battle of Ontario” against the Senators, fell to the defending champion Panthers in seven games in the second round. 

The continued lack of deep runs added to a Stanley Cup drought now at 58 years and counting, representing one of the longest title droughts in North American pro sports. 

“Our responsibility and driving motivation is to add a new chapter to the Maple Leafs’ championship history,” the club’s parent company, Maple Leaf Sports & Entertainment, said in announcing the departure from Shanahan. “It was determined that a new voice was required to take the team to the next level in the years ahead.”

Already operating in hockey-mad Toronto as an Original Six NHL franchise and looking to live up to the team’s 13 Stanley Cups won between 1918 and 1967, the Maple Leafs will soon have an extra level of scrutiny. Rogers Communications, one of the dominant entities in sports, is looking to complete a $3.46 billion deal in the coming weeks to assume majority control of MLSE.

Several key players, including forwards Mitch Marner and John Tavares, are also set to become free agents this summer. 

“There’s been a lot of talk around here about pressure … but pressure is a privilege,” MLSE CEO Keith Pelley said Friday in a news conference. “Good simply isn’t good enough.”

Shanahan, for his part, said he understood the need for MLSE to make a move.

“While I am proud of the rebuild that we embarked on starting in 2014, ultimately, I came here to help win the Stanley Cup and we did not,” he said. “My biggest regret is that we could not finish the job.”

His position will not be filled, and instead, Pelley will lean further on current GM Brad Treliving and head coach Craig Berube.

EXCLUSIVE

Dan Le Batard’s Meadowlark Lands New Deal

Meadowlark Media and DraftKings are sticking together, sources told Front Office Sports. The longtime partners have struck a new deal that keeps DraftKings as a sponsor of several flagship shows. Read Ryan Glasspiegel’s full story here.

For all of our sports media news and analysis, you can subscribe to the twice-weekly “Tuned In” newsletter.

F1’s Monaco Grand Prix Has New Rule to Fix ‘Boring’ Race

Sam Navarro-Imagn Images

The Monaco Grand Prix is one of the most prestigious races in all of motorsports. It’s part of the Triple Crown alongside the Indy 500 and 24 Hours of Le Mans. 

But the actual race has lost its excitement in recent years. Four-time world champion Max Verstappen even called it “boring” last year.

“I should’ve brought my pillow,” Max Verstappen said after a sixth-place finish.

In recent years, there have been changes in the way Formula One cars are built, which have led to a decline in overtakes. According to The Race, there was an average of 32.8 overtakes in 2024, down from 39 in 2023.

But it’s significantly lower at the Monaco GP. Overtakes are even more difficult around the track that runs around the narrow streets of Monaco, the second-smallest country in the world behind only Vatican City. Last year, there were only four overtakes over 78 laps, and, for the first time in history, the order of the top 10 at the start of the race remained unchanged by the time the checkered flag was waved. 

In 2023, amid rainy conditions that often lead to an unpredictable race, there were only 22 overtakes, well below the season’s average overtake count.

The Rule Change

In February, the FIA announced a new rule that mandates drivers to use at least three different sets of tires resulting in a minimum of two pit stops for each car. (F1 has three tire compounds for dry-weather races: soft, medium, and hard.) The requirement for every other race is for each car to use two tire compounds for a dry-weather race, which can be done with just one pit stop. 

This could add additional intrigue to the race as teams have differing strategies. Teams will now have more opportunities to “undercut” their opponents—which is to pit earlier than their opponents to gain an advantage. It also opens the door for more chaos should there be a crash that triggers a safety car—which generally allows teams to pit and change their tires at an advantageous time.

“I think it will definitely help Sunday, especially with strategy. The excitement on Sunday is maybe a bit less than what you will hope,” Ferrari driver Charles Leclerc, who won last year’s race, told Sky Sports in February.

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LOUD AND CLEAR

LPGA’s Hidden Challenge

LPGA

“It’s really, really hard to do that today with women’s golf.”

—Craig Kessler, incoming LPGA commissioner, who was addressing the challenge of visibility for the LPGA during his first interview. He emphasized that, unlike many major sports, fans struggle to consistently find and follow women’s golf on TV or streaming platforms—an issue he plans to prioritize as he works to grow the game. 

You can read more about Kessler’s priorities in David Rumsey’s full story here.

FRONT OFFICE SPORTS TODAY

Why NBA Playoffs Are Setting Records

FOS illustration

The NBA playoffs are delivering big numbers, largely thanks to new faces making up the final four and the stunning comebacks from the Pacers. Ahead of Game 2 against the Knicks, FOS reporter Colin Salao joins to discuss how the late-season stories are rejuvenating the NBA product, with the ratings to back it up.

Plus, No. 1–ranked NASCAR driver Kyle Larson joins us in the studio ahead of attempting the historic “double,” racing in the Indy 500 and the Coca-Cola 600 on the same day.

Watch the full episode here.

STATUS REPORT

Three Up, One Push

Detroit Free Press

Aidan Hutchinson ⬆ The Lions star said Thursday that he’s fully cleared to return to football activities. The defensive end, who sustained a broken fibula and tibia in Week 6, is in line for a new contract next year. He could be the highest-paid edge rusher, a title currently held by Myles Garrett ($40 million average annual value).

David Adelman ⬆ Days after the Nuggets were eliminated from the playoffs by the Thunder, the team removed the interim tag from its head coach. Adelman, who replaced Michael Malone with just three games left in the season, led the No. 4–seeded Nuggets to a first-round win over the Clippers before pushing No. 1 Oklahoma City to seven games.

Lewis Hamilton ⬆ The seven-time world champion said he is working on three movie scripts with his production company, Dawn Apollo. Hamilton, 40, said in 2022 that he would like to focus on making movies after he retires from racing. Dawn Apollo helped create the Formula One movie—simply titled F1—starring Brad Pitt that drops on June 27. 

Cubs ⬆⬇ The team denied a report made by local radio station WSCR-AM 670 that the city had been awarded the 2027 MLB All-Star Game, according to the Chicago Tribune. The team said that “no decision has been made.” The Cubs have not hosted an All-Star Game at Wrigley Field since 1990.

Editors’ Picks

What Pro Team Would Ted Leonsis Like to Buy Next?

by Alex Schiffer
The Monumental Sports & Entertainment CEO would like to grow his empire further.

Darin Ruf Sues Reds Over Career-Ending Knee Injury

by Alex Schiffer
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Advertise Awards Learning Events Video Shows
Written by Eric Fisher, David Rumsey, Colin Salao
Edited by Matthew Tabeek, Catherine Chen

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