You seem to be imagining something else where a man of sin makes a covenant! How can that be, why would a sinful man make a covenant. All covenants are initiated by God!
Here are some things to consider... first of all, I think the text says something like "confirm/strengthen" the covenant (not "create" one, like a wholly new one); and secondly, consider that scripture refers to "my covenant"/"the covenant I made with you" things like that, but also says (in one place) "YOUR covenant..." (a not good one); thirdly, here's something I wrote awhile back (just a portion of it, to try to keep this post short):
[quoting my previous post]
...the
two "
prince" of Daniel 9--
one in verse 25 [referring to Jesus and Lk19:41-44/Zech9:9 having to do particularly with "the city"]...
the other in verses 26,27
--if referring to just
one singular "prince" throughout, then the words "___
THAT SHALL COME" would be
superfluous. If verse 26 were referring to the
same "prince" as in verse 25, then merely to say something like "he" or "the prince" would be sufficient to be speaking of him [/same]. But since the words "[prince]
THAT SHALL COME" is
added (
which would be unnecessary otherwise), this shows a
separate person/prince (from the one in verse 25)
--
the passage seems to be sequential, in that "FROM... UNTO the messiah the prince [Jesus]" happens
first;
then his "shall be cut off but not for himself [or, and have nothing]"
happens next;
then "the people [
OF the prince THAT SHALL COME]" shall destroy the city and the sanctuary
follows that;
then, finally, "
the prince THAT SHALL COME" shall confirm the covenant with the many "FOR ONE WEEK [7-yrs]" [far future] which SEQUENCE agrees with other passages elsewhere
--"
the prince THAT SHALL COME" (Dan9:26) correlates with the "
whose COMING/advent/arrival/presence/parousia" of 2Th2:9a (with 2Th2 chpt covering the entire SPAN OF the 7 years: BEGINNING-2Th2:9a; MIDDLE-2Th2:4; END-2Th2:8b [same as Dan9:27 does])
--so that, Dan9:26[27a] parallels 2Th2:9 at the START of the 7 years, as well as Seal #1 rider on the white horse with a "bow" (which often means "deceit/deception") which is parallel to the FIRST "birth PANG" (of "the beginning of birth PANGS") in Matt24:
4/Mk13:
5 "G5100 -
tis - 'A CERTAIN ONE'" (which would be "the man of sin be revealed" at the START of the 7 years, not at its middle nor at its end--2Th2 is covering all 7 years of the tribulation period, just as the Olivet Discourse [except for the portion in Luke 21:12-24 about the events of 70ad, and fitting earlier in this chronology/sequence, with Lk21:20 speaking of the "Jerusalem compassed with armies" and verse 23's "great distress in the land, and wrath upon this people" and verse 24's "shall fall by the edge of the sword, and shall be led away captive into all the nations..."]).
[end of that portion of my post; there's more, but this is sufficient for the moment and the current discussion
]
Consider these.