After entering this past offseason as two of the top free agents, both Keuchel and Kimbrel remain unsigned two months into the 2019 season after being tendered qualifying offers from their previous teams. Any team that signs a player that declined a qualifying offer would have to surrender a draft pick (as well as the money associated with the pick's slot value).
However, those stipulations disappear at midnight ET on June 2.
Keuchel went 12-11 with a 3.74 ERA and a 1.314 WHIP in 34 starts (204.2 innings) for the Houston Astros last season. The 31-year-old is 0-4 with a 5.74 ERA in five career starts at Tropicana Field, and he is 3-2 with a 2.45 ERA in five career starts at Yankee Stadium.
The southpaw has two All-Star selections, an American League Cy Young award, four Gold Gloves and a World Series championship on his resume during his seven seasons with Houston.
Keuchel told Yahoo Sports' Tim Brown earlier this month that he will not settle "out of principle" and is willing to wait until June 2 to sign if necessary.
Kimbrel, meanwhile, helped the Boston Red Sox win a franchise-record 108 games during the 2018 regular season en route to a World Series title. The closer went 5-1 with 42 saves last season, posting a 2.74 ERA and a 0.995 WHIP while striking out 96 batters in 62.1 innings.
Having spent three years in Boston, Kimbrel has experience pitching in the AL East. He has a 1.23 ERA in 15 career outings at Tropicana Field.
According to Rosenthal and Tolentino, Tampa Bay views Kimbrel as a bigger priority than Keuchel even with starter Tyler Glasnow (6-1, 1.86 ERA) expected to miss more than a month with a mild right forearm strain. The Rays currently have the majors' top pitching staff.
Meanwhile, the Yankees roster has been depleted by injuries, both on the mound and in the field. Luis Severino, James Paxton and CC Sabathia are all currently on the injured list.
Still, New York (32-17) entered Saturday with a 2.5-game lead over Tampa Bay (29-19) in the AL East. The Rays do, however, sit four games up in the wild-card race.