NON RADAR APCH DEP CTLR CLBED AN SMT THROUGH THE ALT OF AN SMA WITHOUT ENSURING SEPARATION.

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SMA X WAS INBOUND TO SJT FROM THE E; HE HAD BEEN CLRED TO THE WOOLE NDB VIA THE 090 RADIAL TO THE SJT VOR; THEN DIRECT TO WOOLE MAINTAIN 5000. HE WAS TOLD TO RPT XING THE VOR. SMT Y TOOK OFF ON RWY 36 WITH A R TURN ON COURSE NEBOUND TO MAINTAIN 4000. HE TOOK OFF AT XA14. AT XA16 SMT X RPTED XING THE VOR THEN HEADED SW TO WOOLE. AT XA17 SMT Y RPTED 2 1/2 MI NE OF THE VOR. I CLBED HIM TO 6000. RIGHT AFTER THAT I GAVE THE SMA X HOLDING AT WOOLE NDB; TO HOLD SW OF WOOLE ON THE LOC; L TURNS 1 MIN LEGS WITH AN EFC. HE ASKED ME TO REPEAT THE INSTRUCTIONS WHICH I DID. I THOUGHT I GOT AN ACKNOWLEDGEMENT; BUT UPON LISTENING TO THE TAPE; ALL YOU HEAR IS A SQUELCH BREAK. I HAD ASKED THE SMA X TO RPT XING WOOLE. AT XA23 I ASKED THE SMA X IF HE HAD CROSSED WOOLE. HE SAID NO; HE HAD BEEN HDG TO WOOLE WHEN I TOLD HIM TO GO BACK TO THE VOR. I TOLD HIM TO PROCEED TO WOOLE RPT XING THE VOR. HE SAID HE WOULD RPT XING THE VOR GOING DIRECT TO WOOLE. IT WAS XA23:19. AT XA25:20 I ASKED HIM HIS DME; SINCE HE HAD NOT RPTED XING THE VOR. HE SAID HE WAS 7.8 DME JUST COMING UP ON WOOLE. BASED ON THE FACT THAT HE HAD RPTED XING THE VOR (THE SMA X THAT ITS) AND LATER WHEN ASKED WHERE HE WAS AND HE SAID THE VOR; HE STATED THAT HE HAD BEEN ON HIS WAY TO WOOLE WHEN I TOLD HIM TO GO TO THE VOR. AND THE FACT THAT WHEN I TOLD HIM TO GO TO WOOLE RPT XING THE VOR AND 2 MINS AND 1 SECOND LATER HE WAS AT WOOLE; I KNEW SEPARATION EXISTED WHEN SMT Y CLBED TO 6000 NE OF THE VOR BUT SINCE THERE IS NO CLR ACKNOWLEDGEMENT OF THE SMA X RECEIVING THE HOLDING INSTRUCTION AT WOOLE; IT CANNOT BE PROVEN.