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db<>fiddle
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CREATE TABLE T(
ID INT,
UserID int,
Roles nvarchar(50)
);

INSERT INTO T VALUES (1,1,'["Admin","A1","A2"]');
INSERT INTO T VALUES (2,2,'["B1","A2"]');

SELECT
col1,
UserID
FROM T t1
CROSS APPLY
OPENJSON(t1.Roles)
WITH
(
col1 varchar(50) N'$'
) AS a



col1 UserID
Admin 1
A1 1
A2 1
B1 2
A2 2