The Blue Jays are likely to seek pitching prospects in exchange for impending free agent J.A. Happ, which seemingly puts the Yankees at the front of the line to acquire the veteran southpaw, per MLB Network insider Joel Sherman.
• Stay up to date on the latest trade talk
Toronto's farm system is rich with promising position players such as Vladimir Guerrero Jr., Bo Bichette and Anthony Alford, but lacking on the pitching side.
Meanwhile, 16 of New York's top 19 prospects are pitchers, according to MLB Pipeline's rankings. While Justus Sheffield likely won't be on the table in any potential Happ trade, the Yankees may be able to swing a deal for the 35-year-old by sending a pair of their mid-level pitching prospects to the Blue Jays.
• Top 30 Prospects:Yankees | Blue Jays
Sherman compares Happ to Scott Kazmir and Rich Hill, two veteran lefties who were dealt before the non-waiver Trade Deadline in years past as they were heading toward free agency.
In 2015, the A's traded Kazmir to the Astros for Daniel Mengden and Jacob Nottingham, and Oakland send Hill to the Dodgers in 2016 along with Josh Reddick for Jharel Cotton, Frankie Montas and Grant Holmes.
Happ has a proven track record of succeeding in the typically relentless American League East, which makes him particularly attractive to the Yankees.
Happ has also been traded during the season three times in his career, so he shouldn't be fazed by another move. Most recently, he went from the Mariners to the Pirates in July 2015 and posted a 1.85 ERA over 11 starts for Pittsburgh before signing with Toronto in the following offseason.
Since the outset of 2015, Happ has gone 51-26 with a 3.46 ERA and a 1.21 WHIP over 105 games (104 starts) for the Mariners, Pirates and Blue Jays, including a 10-3 record with a 3.62 ERA in 2018.