GL's Edmund (David Andrew Macdonald) — Arthur Cohen/PGP

He's back! In honor of David Andrew Macdonald's return to GL next week as Springfield's dastardly dark prince Edmund Winslow, Digest compiled a timeline of memorable moments and dirty deeds from Eddie's troubled past, including San Cristobel crimes and Springfield snafus.

Edmund was born into royalty as the second son to the San Cristobel throne. His father, Prince George, considered Edmund a troubled failure and favored his older brother Richard. This caused years of emotional turmoil for the often-neglected Edmund, who also frequently suffers debilitating headaches and other mental instabilities caused by a childhood horseback riding accident. His lifelong jealousy/hatred of Richard fueled the majority of his early misdeeds, including his long held desire to abdicate the family throne.

Sibling Rivalry: Edmund (Macdonald) and Richard (Bradley Cole) faced off on several occasions. — Robert Milazo

Edmund was first introduced to GL viewers when Reva went to San Cristobel to investigate her "missing years." When she met Edmund, he was hell-bent on keeping her past as Princess Catherine, Richard's one-time wife, a secret. Reva's memory eventually returned and she recalled that Edmund was once her archenemy, as he had tried to kill her and her young son Jonathan, the heir to the throne, years before. When the truth came out, Edmund kidnapped Reva, told her Jonathan was dead and used her as leverage to win back the throne from Richard. The feuding brothers fought to the death and Edmund fell over a cliff, but survived. He later resurfaced and, believing Richard was on a plane to Springfield, sabotaged the flight that left Beth, Phillip and Jim Lemay stranded in the mountains. He was eventually caught and imprisoned for his crimes.

Edmund faced execution but was exonerated, thanks to Cassie (Richard's then-wife), who had him shipped to Springfield to work at Spaulding Enterprises and redeem himself. Still hungry for the throne, however, Eddie tried to sabotage Richard by exposing Cassie's stripper past and fooled his brother into thinking he was sterile. Edmund also got tangled up with the Santos mob and fell in love with Beth. After her then-beau Jim Lemay died, Eddie offered to give Beth a fresh start with him back in San Cristobel. She accepted, so they returned to the island together.

After marrying Beth, Edmund discovered he was the real heir to the throne. (Richard turned out be George's love child with another woman.) So, he overthrew the monarchs and kidnapped Richard and Cassie in the palace tower. When Richard escaped, the battling bros fought again. Edmund was stabbed and presumed-dead. Cassie, meanwhile, remained his hostage. When Beth eventually found Cassie, she was outraged so he locked her up, too. Edmund attended Richard's "funeral," but later realized he'd been duped. Richard was still alive and had come to rescue Beth and Cassie. Eddie was deemed a criminal once again and kicked off the throne. Beth later fled to Mexico to get a divorce from Edmund, where she presumably died in a storm.

Familiar Face: Eddie Ivories (Macdonald) hatched a devious plan with Beth's doppelgänger, Lorelei (Beth Chamberlin). — Lorenzo Bevilaqua/PGP

Edmund moved to Chicago and scored a piano bar gig under the name Eddie Ivories. He met a woman named Lorelei, who was actually Beth's alter, and decided to use her to win back his power via swindling the Spauldings. When he returned, however, Richard was dead. He was arrested for his crimes, again.

During this time, he tangled with the Spauldings, tried to convict Reva for pulling the plug on Richard and burned his brother's will. He also came face-to-face with his long lost nephew, Jonathan. After an ill-fated fling with Carmen Santos, Edmund was hired by Alex to kidnap Roy Baker. Edmund also vowed to become a better man and make up for how he mistreated Richard by winning over Cassie, which he eventually did, by helping her dedicate a library in Richard's honor and despite conflict with her new beau and Richard look-alike, Jeffrey.

Edmund purchased the Jessup farm from Cassie and met a woman named Dee (a.k.a. Dinah, Cassie's biggest rival), who had been impersonating Cassie overseas. The duo became allies to keep their secrets hidden: Dinah was wanted for murdering Hart and Eddie's knowledge of Jeffrey impersonating Richard. Edmund's rivalry with Jeffrey also intensified and during a scuffle, the barn went up in flames, Jeffrey was hit over the head and Dinah was exposed. By the end of the year, Cassie and Edmund were engaged.

Now married, Edmund and Cassie wanted a baby, but his jealousy and suspicions of Cassie's infidelity overshadowed their efforts and strained their marriage. After Cassie miscarried, they started in vitro. Edmund later struck a secret deal with Dinah to have her be a surrogate, hoping it would save his marriage to Cassie. She was understandably miffed when Dinah spilled the truth, but when along with the plan. Dinah lost the baby, but she and Edmund kept it hidden from Cassie and faked the pregnancy, anyway. In a desperate act to continue the ruse, Edmund kidnapped Michelle's newborn and presented it to Cassie, claiming Dinah left town after giving birth. He kidnapped Dinah and held her hostage in a replica of the Jessup farm to keep her quiet.

After Cassie learned the truth about baby Hope, she called it quits with Edmund for good. He returned to San Cristobel and entered a mental facility. When Cassie came to visit, Edmund spilled the truth about Jeffrey's past impersonations of Richard.

Kooky Kin: Troubled Will (Seamus Davey Fitzpatrick) wasn't really an angel after all, and put his uncle Edmund (Macdonald) into a coma. — George De Sota/JPI

Cassie was forced to visit Edmund again and ask for his help during her custody battle with Will's adoptive father, Alonzo. During a power outage, Edmund escaped, killed Alonzo and eventually returned to Springfield to testify on Cassie's behalf during the court case. It was later revealed that he had maintained a relationship with problem child Will for several years during Cassie's absence. Taking a cue from his uncle, a jealousy driven Will, thinking Edmund was trying to take Cassie from him, pushed his uncle over the church balcony during a Christmas pageant. Edmund fell into a coma and Jeffrey gave him sedatives to keep him comatose; Will was sent away to a school for troubled kids.