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Blue Jays eyeing Bucs pitchers (sources)

@jonmorosi
August 24, 2020

Longstanding friendships between the Blue Jays' and Pirates' front offices nearly helped Toronto play its 2020 home games at Pittsburgh's PNC Park. While Pennsylvania's state government ultimately rejected that agreement, the Blue Jays and Pirates still could come together for a more conventional transaction: a trade that bolsters Toronto's pitching

Longstanding friendships between the Blue Jays' and Pirates' front offices nearly helped Toronto play its 2020 home games at Pittsburgh's PNC Park.

While Pennsylvania's state government ultimately rejected that agreement, the Blue Jays and Pirates still could come together for a more conventional transaction: a trade that bolsters Toronto's pitching staff and adds momentum to Pittsburgh's rebuild.

The Blue Jays have emerged as buyers ahead of Monday's Trade Deadline, and sources say Pirates right-handers Trevor Williams and Chad Kuhl are among the rotation upgrades they are considering.

With starting pitchers Matt Shoemaker, Nate Pearson and Trent Thornton on the injured list, the rotation has become the Blue Jays' most urgent need. Williams and Kuhl aren't eligible for free agency until after the 2022 season -- which makes them especially appealing for a Toronto team with only two starters, Hyun Jin Ryu and Tanner Roark, signed to guaranteed contracts for '21.

In a season without in-person scouting, connections among executives from different teams and pre-existing background knowledge of players are more important than ever. In that regard, it's hard to imagine a better trade fit than the one between the Blue Jays and Pirates.

Pirates general manager Ben Cherington and assistant general manager Steve Sanders are two of the most qualified people in the world to evaluate the Blue Jays' prospects for a potential trade. Before arriving in Pittsburgh last offseason, Cherington was Toronto's vice president in charge of player development; Sanders was the club's scouting director.

Cherington's ties to the Blue Jays' top leadership -- president/CEO Mark Shapiro and general manager Ross Atkins -- began more than two decades ago. Cherington's first full-time job in Major League Baseball was in 1998 with the Cleveland Indians, where Shapiro was then a top baseball operations executive and Atkins a Minor League player.

At a time when comprehensive information on prospects at alternate training sites can be elusive, the trust between the Blue Jays and Pirates could be one key factor in facilitating a deal.

Of course, Toronto officials are monitoring other potential acquisitions around the league. The Angels are an intriguing possibility for a larger trade, given that they have available players in multiple areas of need for Toronto: infielder Tommy La Stella, right-handed starter Dylan Bundy and veteran catcher Jason Castro.

The Blue Jays also are open to trading for a rental starter, such as Seattle's Taijuan Walker, if they can't acquire a pitcher who is under control for 2021 and beyond.

The Blue Jays' chances of earning a postseason berth improved to 61.9 percent with Monday's comeback win over the Rays, according to FanGraphs.com. Toronto is 7-3 since the team's top position player, Bo Bichette, landed on the injured list.

Teams hovering around .500, as the Blue Jays are, typically aren't among the most aggressive buyers at the Trade Deadline. But this year's expanded playoff format has created incentives to act boldly, particularly for a Toronto team that last reached the postseason in 2016.

Under this season's unique rules, a league's No. 8 seed is more valuable than the No. 4 seed in an ordinary year; the former will earn a berth in the best-of-three first round, whereas the latter only clinched home-field advantage in a Wild Card Game.

Jon Paul Morosi is a reporter for MLB.com and MLB Network.