Perrotto: Three Winter Meetings Trade Proposals for Pirates

Maybe it is an omen.

Pittsburgh Pirates general manager Ben Cherington and I were on the same flight from Pittsburgh to Dallas. Then we ate lunch at the same restaurant.

Maybe Cherington hopes to get some free advice as MLB’s Winter Meetings begin today at the Dallas Anatole and continue through Wednesday. Perhaps that is why we keep running into each other.

It is doubtful that it is anything more than a coincidence, though. I’ve been trying to give Pirates GMs free advice going back to Syd Thrift’s days nearly four decades ago, but no one has ever taken me up on the offer.

Regardless, my free advice for Cherington to trade for a first baseman, a position he has struggled to fill adequately since being hired after the 2019 season. Here are three trade proposals at no charge — a price Pirates owner Bob Nutting would surely like.

Triston Casas

The Boston Red Sox are open to trading Casas and moving Rafael Devers to first base. Casas would be a good fit for the Pirates as he is 24, bats left-handed and is not eligible for free agency until 2028.

Casas was limited to 63 games this year because of injuries and hit .241/.337/.462 with 13 home runs. However, he had 24 homers in 2023 as a rookie. Casas also isn’t arbitration-eligible, meaning his salary will be around the MLB minimum of $760,000.

The Red Sox would want a lot in return, and the Pirates would likely have to start a multiple-player offer with right-hander Mitch Keller. Adding second baseman Nick Gonzales and pitching prospect Jesus Castillo might complete the deal.

Offloading the $72 million remaining on the final four years of Keller’s contract would allow the Pirates to be more serious players in the free-agent market.

Josh Naylor

Naylor would also give the Pirates a powerful left-handed hitter. He helped lead the Cleveland Guardians to the American League Central championship in 2024 with a .243/.320/.456 slash line and a career-high 31 homers in 152 games.

Though just 27, Naylor is entering the final year of his contract and likely would be a one-and-done with the Pirates. However, he hit .308 just a year ago and would boost the Pirates’ chances of reaching the postseason for the first time since 2025. Naylor is expected to have a $12-million salary next season while going through the arbitration process one last time.

The trade cost might not be so high for a player with only one year of club control. An offer of pitching prospects Thomas Harrington — he could help the Guardians immediately — and Inmar Lobo could get the deal done.

Yandy Diaz

Diaz won the AL batting title with a .330 average in 2023 with the Tampa Bay Rays. He didn’t follow with a strong season this year but did slash .281/.341/.414 with 14 homers in 145.

Diaz is a little older at 33 and being a right-handed hitter is not ideal but the Pirates need someone who can help them win now. Diaz will make $10 million next year, and his contract includes a team option fort $12 million in 2026 with no buyout.

The Rays like to trade their players a year before they become free agents and take pride in salvaging the careers of struggling players. Thus, offering right-hander Jose Ortiz, catcher Henry Davis and infielder/outfielder Ji Hwan Bae might intrigue Tampa Bay.

So, Cherington can make three trade proposals this week. And he doesn’t even have to buy me lunch for the ideas.