Meet the Sellers: Despite a hot start to the season, the Pirates are in a familiar position

Say what you want about the AL Central this year, but the Pittsburgh Pirates were MLB’s darling team for part of this season. It was only May 11th that Pittsburgh was pacing their division, but unfortunately, that has been usurped from them. The steady Milwaukee Brewers and the up-and-coming Cincinnati Reds are vying for the division now, and with Pittsburgh’s regression, it may be time to see what the trade market can offer them.

Pittsburgh has reached that time of year in which they are seeing a lot of their younger and developing players, particularly on the pitching side. They’ve locked up Bryan Reynolds and Ke’Bryan Hayes for several years, and they’re hoping other youngsters like Oneil Cruz and Rodolfo Castro are staples for their competitive window.

Prior to this season, the Pirates signed a few veterans to short-term deals for a multitude of reasons. One was to assist their growing club in their development, and the other being for articles just like this one. Pittsburgh and Toronto have solid trade history with each other – let’s see if 2023 could bring similar vibrations.

August 21, 2008: Traded Jose Bautista to Toronto in exchange for Robinson Diaz.

July 30, 2012: Traded Brad Lincoln to Toronto in exchange for Travis Snider.

August 1, 2016: Traded Francisco Liriano, Harold Ramirez, and Reese McGuire to Toronto in exchange for Drew Hutchison.

January 10, 2023: Traded Zach Thompson to Toronto in exchange for Chavez Young.

This wouldn’t be the first time that McCutchen and the Blue Jays are sitting in potential crossroads. The 36-year-old former MVP was a potential free agent target this past offseason before signing a one-year, $5 million deal with the Pirates. Honestly, if it wasn’t going to be the Blue Jays, McCutchen returning to Pittsburgh was the perfect consolation prize. McCutchen spent his first nine years with the Pirates, racking up four top-5 MVP finishes, five All-Star appearances, and three playoff appearances.

This season, while not posting statistics of that calibre, McCutchen is still one of Pittsburgh’s best power hitters. Through 77 games, McCutchen is slashing .266/.377/.797 with 10 home runs, 28 RBIs, and 12 doubles. He’s primarily served as Pittsburgh’s DH this year with minimal outings in right field, and I think that’s a very reasonable role for him to play with the Blue Jays.

McCutchen has had quite a decorative career, and it wouldn’t surprise me at all if he wants to retire as a Pirate. Still, the Blue Jays may want to give him the chance to make one last playoff push.

All I see is Santana homering off of Tim Mayza in last year’s Wild Card round, but now is the time for a new Santana memory. Maybe it’s with the Jays?

Like McCutchen, Santana is currently on a one-year deal with the Pirates, with his being for $6.75 million. Santana has played in 88 games this year and is batting .230 with a .698 OPS. He has hit 9 homers with 45 RBIs, and his 22 doubles are tied for 10th in the NL.

Santana has a wealth of postseason experience with the time he spent in Cleveland several years back, as well as his stint last year in Seattle. The biggest benefit with him is that he can bat from both sides of the plate, and he’s hit better as a right-handed hitter than when he bats left, something that matches a Toronto need. Furthermore, Santana has a .278 batting average and a .765 OPS with runners in scoring position. That type of contribution to Toronto’s lineup would be extremely welcome.

Aside from Keller, Bednar would generate the largest and most profitable return among Pittsburgh’s assets. Bednar is in his fifth major league season and his last three have quietly been some of the best for a reliever in the game. He was part of a three-team deal in January of 2021 that sent Joe Musgrove to the Padres, and ever since putting on a Pirates uniform, he’s proven to be one of the better players in that trade.

Bednar posted a 2.23 ERA in ’21 with an 11.4 K/9 through 61 outings, earning him 8th place in NL Rookie of the Year voting. He followed that up in 2022 with a 2.61 ERA and a 12.0 K/9, finding himself on his first All-Star roster. He landed on the All-Star team again this season, and he’s on his way to posting more career-bests; through 37 games, Bednar has a 1.18 ERA, 0.092 WHIP (disgustingly good), and a 10.9 K/9 versus a minuscule 1.7 BB/9.

Serving as Pittsburgh’s closer, Bednar is also on pace to set a personal best for saves in a season, needing only one more to tie the 19 he had last year. He features a fastball, curveball, and splitter that have whiff percentages in the mid-to-late 30s, and his Baseball Savant page is loaded with red numbers if you’re into that kind of thing.

If the Blue Jays want to blow the roof off of the reliever market, trading for Bednar would do just that. He won’t be a free agent until 2027, so they would be able to have him under team control for a couple of years, a preference for Ross Atkins.

Hill has quite the career resume, with the Pirates making it 12 teams for which he has played. I mean, he’s truthfully approaching Edwin Jackson levels. Although he’s 43 years of age, he is still one of the more durable arms in Pittsburgh’s rotation. This season, Hill has made 20 starts with a 4.84 ERA, 1.45 WHIP, and a 7.7 K/9. Hill operates mainly with his fastball and curveball, but he sprinkles in a flurry of other pitches (cutter, sweeper, changeup, among others).

He signed a one-year, $8 million deal for this year, and if the Jays may not be the best fit for him, there are several teams needing starting pitching depth of any kind. Hill won’t blow anyone away with his stuff, but he’s only made three starts this season in which he hasn’t recorded at least five innings.

I won’t get into the discourse about Toronto’s need for a starting pitcher, there are arguments for and against them doing it. Keller fought multiple injuries in ’20 and ’21, but he’s stayed healthy across the last couple of seasons and it’s paying off for his development. He’s a younger option for the Blue Jays who is having a career-best season, culminating in his first All-Star game appearance. Keller has made 20 starts this year with a 3.73 ERA, 1.16 WHIP, and a 9.5 K/9. His ERA took a hit earlier this week after allowing 8 runs to the Guardians, but he’s had multiple stellar outings against AL East foes in Boston and Baltimore this season.

Keller features a six-pitch mix, starting with a fastball that sits around 95 mph on average. He won’t hit free agency until 2026, so he will probably require a highly touted return. With Alek Manoah and Hyun-Jin Ryu still being wild cards for Toronto’s rotation, Keller would be a great option down the stretch for the Blue Jays.

It was announced on Wednesday that Crowe would be designated for assignment by the Pirates. Part of the 2020 deal that sent Josh Bell from Pittsburgh to Washington, Crowe is on the backend of a stint on the 60-day injured list for right shoulder discomfort. Now that the Blue Jays could acquire him via waivers, he may be worth taking a flyer on.

Due to the aforementioned injury, Crowe has only appeared in five games this year, and the numbers were not pretty. In those five games, he’s given up nine hits and nine walks, plus a home run. The small sample size isn’t entirely fair to Crowe given we haven’t seen him pitch in the majors after his injury, and his rehab numbers in A and AAA games have been very encouraging.

Last season was Crowe’s first full season in the majors, pitching in 60 games with a 4.38 ERA, 1.39 WHIP, and an 8.1 K/9. Walks were still an issue for him last season as they were for the beginning of this season, but he’s only 28 years of age and the buzz suggests he won’t last very long on the waiver wire.

Joe has bounced around a little bit through his first four major league seasons. He was dealt to the Pirates last season by the Rockies, and he’s having himself a relatively nice season. In 84 games, Joe has a .244 batting average with a .760 OPS, 7 home runs, 25 RBIs, and 18 doubles. He can play some first base, but he can also play in the corner outfield positions.

One of Joe’s best qualities is his ability to mash left-handed pitching; against southpaws this year, Joe is slashing .298/.400/.921 with four homers. Joe won’t be a free agent until 2028, and he won’t even be arbitration eligible until 2025. Given that the trade that sent him to the Pirates required only a prospect in return coupled with him already being some sort of a journeyman, Toronto may be able to acquire him for cheap. It just depends on how Pittsburgh views him as a part of their future.

A long-time Tampa Bay Ray, Choi is in his first year with the Pirates in what will be his final season before free agency. Choi has missed a large chunk of this season with a strained left Achilles tendon, but he was activated off the injured list shortly before the All-Star break.

Choi’s numbers aren’t anything to throw a party for, although the injury didn’t help him any. Through only 17 games, Choi is batting .182 with a .643 OPS, 4 home runs, and 8 RBIs. Again, this season hasn’t turned out how Choi imagined it going, but he proved himself as a power hitter during previous his five years with the Rays. Toronto is not likely to acquire him I’d say, but the experience plus the cheap deal earns him a spot on this list.