Well here is the rub. Not only is a cursor going to perform far worse, you have only 1 row of data so you can't use a cursor anyway. You need to split your text lines into separate rows first.

This seems to work on your example.

;WITH Actions (message) AS

(

;WITH Actions (message) AS

(

SELECT '< br>20:32:12 [Rachel] Thank you for contacting Our Company. How may I assist you?< br>< br>20:32:31 [Marina Galofaro] What is the mailing address to mail a check?< br>< br>20:32:49 [Rachel] I''m happy to provide you with the mailing address.< br>< br>20:33:22 [Marina Galofaro] O kay, Thank you.< br>< br>20:33:28 [Rachel] One moment please while I provide a link with directions to mail your payment.< br>< br>20:34:05 [Rachel] Please click <a href="http://company.custhelp.com/app/answers/detail/a_id/1050/kw/payment" target="_blank">here</a> to view how to mail a payment.< br>< br>20:35:07 [Rachel] Is there anything else I can help with, Marina? < br>< br>20:35:56 [Marina Galofaro] No, Thank you!< br>< br>20:36:00 [Marina Galofaro] Session Disconnected< br>'

)

,Transcript(Message) as

(

select Item

from Actions

cross apply dbo.DelimitedSplit8K(replace(replace(message, '< br>< br>', char(10)), '< br>', ''), char(10))

)

,Operators (username) AS

(

SELECT 'Rachel'

)

SELECT

operator = LEFT(operator, CHARINDEX(']', operator)-1)

,TextOfMessage = LTRIM(RIGHT(operator, LEN(operator)-CHARINDEX(']', operator)))

FROM Transcript

CROSS APPLY

(

SELECT SUBSTRING(message, CHARINDEX('[', message)+1, LEN(message)) as operator

) a

LEFT JOIN Operators ON LEFT(operator, CHARINDEX(']', operator)-1) = username

WHERE username IS NULL