A bifunctional compound of Formula X: wherein: the Targeting Ligand is capable of binding to CDK8, wherein the Targeting Ligand is of Formula TL-I: or an enantiomer, diastereomer, stereoisomer, or pharmaceutically acceptable salt thereof, wherein: A is X is N or CH; X 2 is N or CH; X 3 is N or CH; X 4 is N or CH; each R 1 is independently (C 1 -C 4) alkyl or (C 1 -C 4) haloalkyl; each R 2 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; each R 3 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; each R 4 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; and t, n, o, and r are each independently 0, 1, 2, or 3; wherein the Targeting Ligand is bonded to the Linker via the next to the Linker is a bond or a carbon chain that serves to link a Targeting Ligand with a Degron, wherein, the carbon chain optionally comprises one, two, three, or more heteroatoms selected from N, O, and S, and wherein, one or more chain carbon atoms in the carbon chain are optionally substituted with one or more substituents selected from oxo, (C l - C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 3) alkoxy, OH, halogen, NH 2, NH(C 1 -C 3) alkyl, N(C 1 -C 3) 2, CN, (C 3 -C 8) cycloalkyl, heterocyclyl, phenyl, and heteroaryl; and the Degron is capable of binding to a ubiquitin ligase, wherein the Degron is of Formula D1: or an enantiomer, diastereomer, or stereoisomer thereof, wherein: Y is a bond, (CH 2) 1-6, (CH 2) 0-6 -O, (CH 2) 0-6 -C NR 11, (CH 2) 0-6 -NR 11 C, (CH 2) 0-6 -NH, or (CH 2) 0-6 -NR 12; Z is C or C(R 13) 2; R 11 is H or C 1 -C 6 alkyl; R 12 is C 1 -C 6 alkyl or C -C 1 -C 6 alkyl; each R 13 is independently H or C 1 -C 3 alkyl; each R 14 is independently C 1 -C 3 alkyl; R 15 is H, deuterium, C 1 -C 3 alkyl, F, or Cl; each R 16 is independently halogen, OH, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy; q is 0, 1, or 2; and v is 0, 1, 2, or 3, wherein the Degron is covalently bonded to the Linker via A is X is N or CH; X 2 is N or CH; X 3 is N or CH; X 4 is N or CH; each R 1 is independently (C 1 -C 4) alkyl or (C 1 -C 4) haloalkyl; each R 2 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; each R 3 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; each R 4 is independently (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, halogen, OH, or NH 2; and t, n, o, and r are each independently 0, 1, 2, or 3; wherein the Targeting Ligand is bonded to the Linker via the next to the Linker is a bond or a carbon chain that serves to link a Targeting Ligand with a Degron, wherein, the carbon chain optionally comprises one, two, three, or more heteroatoms selected from N, O, and S, and wherein, one or more chain carbon atoms in the carbon chain are optionally substituted with one or more substituents selected from oxo, (C l - C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 3) alkoxy, OH, halogen, NH 2, NH(C 1 -C 3) alkyl, N(C 1 -C 3) 2, CN, (C 3 -C 8) cycloalkyl, heterocyclyl, phenyl, and heteroaryl; and the Degron is capable of binding to a ubiquitin ligase, wherein the Degron is of Formula D1: or an enantiomer, diastereomer, or stereoisomer thereof, wherein: Y is a bond, (CH 2) 1-6, (CH 2) 0-6 -O, (CH 2) 0-6 -C NR 11, (CH 2) 0-6 -NR 11 C, (CH 2) 0-6 -NH, or (CH 2) 0-6 -NR 12; Z is C or C(R 13) 2; R 11 is H or C 1 -C 6 alkyl; R 12 is C 1 -C 6 alkyl or C -C 1 -C 6 alkyl; each R 13 is independently H or C 1 -C 3 alkyl; each R 14 is independently C 1 -C 3 alkyl; R 15 is H, deuterium, C 1 -C 3 alkyl, F, or Cl; each R 16 is independently halogen, OH, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy; q is 0, 1, or 2; and v is 0, 1, 2, or 3, wherein the Degron is covalently bonded to the Linker via