Pirates Insider Gives Probabilities of Player Trades

Kiner-Falefa is on an expiring contract, so it should have gone without saying that he would be dealt within the next few days. There’s been no indication that he and the Pirates have discussed a contract extension. Other Pirates who can become free agents after this season, and who are certain to be traded, are Caleb Ferguson, Andrew Heaney, and Tommy Pham.

As the Pirates Rumor Mill Turns

Seeing such high odds on Bednar, Hayes, and Keller is all one needs to see to declare general manager Ben Cherington’s five-year plan (now in its sixth year) an abject failure, as if that wasn’t evident when owner Bob Nutting fired manager Derek Shelton, Cherington’s hand-picked man to lead the rebuilding effort, after 38 games. Explaining why Cherington didn’t follow Shelton out the door, Nutting told Jason Mackey of the Post-Gazette, “I don’t think that blowing everything up 38 games into the year is gonna help us [perform better.] I think that would be distracting. I think that would get us off track.” Cherington did well in the recent draft. We’ll see whether his trade deadline performance makes Nutting regret those words.

Pirates Relief Pitchers are a Hot Commodity

Nutting reportedly blocked previous efforts to trade Bednar. Presumably, he won’t stand in the way now. There have been credible rumors connecting Bednar and Santana to the Philadelphia Phillies. After a subpar 2024 season and a rough start to 2025 that resulted in a trip to Triple-A Indianapolis, Bednar has regained the form that made him an All-Star in 2022 and 2023. In 36 games at the All-Star break, he’s 2-5 with 13 saves in 13 opportunities, a 2.53 ERA, 2.02 FIP, 1.125 WHIP, and 170 ERA+. He’s a popular local product from Mars – the town 40 minutes north of Pittsburgh, not the planet. He’s also been a public relations superstar for his charitable work and countless public appearances on the Pirates’ behalf.

Meanwhile, Santana, who slid into the closer’s role in Bednar’s absence, has arguably been even more effective. He’s 3-2 with five saves in six opportunities, a 1.56 ERA, 2.49 FIP, 0.818 WHIP, and 274 ERA+ in 40 games. Last year, he was a waiver pickup from the New York Yankees, for whom he had a 6.26 ERA. It must be frustrating for Pirates scouts to have identified Santana as a bounce-back candidate when nobody else did, only to see him last only parts of two seasons with the team if he’s dealt away.

He’s Their Man, Until He’s Not

It must be equally frustrating for Nutting if Keller is sent packing into just the second year of a “you’re-our-man” $77 million contract extension. Keller was an All-Star in 2023. This season, he’s pitched better than his 3-10 record would suggest. He has a 3.48 ERA, 3.33 FIP, 1.143 WHIP, and 123 ERA+ while leading the majors with 20 starts. He’s pitched at least six innings in his last 13 starts. The rumor mill has connected the Pirates right-hander to the Chicago Cubs and, more recently, the Yankees. The Pirates meant him to be the veteran presence who would anchor a rotation of young prospects. Sadly, his exit would mean future free agent signings of veteran pitchers intended to be that same anchor, but who won’t be the same caliber as Keller.

If Keller is traded, the question becomes, will the Pirates get fleeced in the deal? The only other time Cherington traded a starter of Keller’s caliber was in January 2021, when he traded Jameson Taillon to the Yankees for four prospects. Three have since been designated for assignment. The jury’s still out on the fourth, 23-year-old infielder Maikol Escotto. However, he’s listed nowhere among the Pirates’ top 30 prospects.

Erasing a Mistake

That a team would take on Hayes and his hefty contract is a blessing for Pittsburgh. The rumor mill has connected the Pirates third baseman to the Cubs, Yankees, and Detroit Tigers. Hayes is owed the remainder of a $7 million salary for this year and another $30 million through 2029. In 2030, there’s a $12 million team option with a $6 million buyout. In his rookie year, the pandemic-shortened 2020 season, Hayes hit .376/.442/.682, 5 HR, and 11 RBI. This writer believes that any stats from the 2020 season should be viewed as aberrations. With the haste with which that season was organized, some players were more prepared than others. The Pirates didn’t share that belief, however, and hastily signed Hayes to a lucrative deal that he’s never lived up to.

Since 2021, Hayes has hit .250/.303/.358, 34 HR, and 196 RBI for an OPS+ of 83, all unacceptable figures for a corner infielder. As with Joe Mauer’s contract with the Minnesota Twins, the Hayes deal has become an albatross that has prevented more meaningful expansions of payroll. (Twin fans, don’t beat me up in the comments section. Mauer is rightfully in the Hall of Fame for the three batting titles he won as a catcher. Afterwards, however, the small market Twins paid $23 million a year for eight years for a singles-hitting first baseman. They had two winning seasons and one Wild Card appearance during those years.)

As Hiles noted on the radio, Hayes, a strong defender who won a Gold Glove Award in 2023, makes sense for a team with a powerful lineup. That team isn’t the current Pirates, and it won’t be unless they cash in some trade chips for some bats.

“Chill Out”

For Reynolds, underperforming this season and with a stiff no-trade clause, a 15 percent chance seems about right. Former major leaguer Evan Longoria took him to task on social media about the no-trade, posting, “Buddy never wants to win.” Reynolds’ reply: “[C]hill out[,] keyboard warrior.”

Hiles also correctly pointed out that Davis has emerged as the Pirates’ best option at catcher. He should remain with Pittsburgh and deserves more playing time than he’s been getting.

The Last Word

No matter how the Pirates try to color it, this will likely be a second rebuilding effort akin to when Cherington first took over. From the time Cherington took the job in 2020 through the 2021 deadline, he traded nine major league players. In return, he received 23 prospects. Only 10 remain Pirates property, and only four have reached the major leagues. Pirates fans continue to await the arrival of highly touted prospects Eddy Yean and Hudson Head, acquired in those deals. It seems that around two dozen teams, give or take, consider themselves buyers. With trade chips like Bednar, Hayes, Keller, and Santana, and the law of supply and demand in his favor, Cherington needs to do better this time around. Much better.

You can hear Hiles discuss the above probabilities here: