Widmore and Desmond

It seems to me that Charles Widmore has been training and motivating Desmond for many years. Instead of marrying Ruth, Desmond "woke up" on a sidewalk, not knowing how he got there and decided to "follow" Brother Campbell - who’s connected to Eloise Hawking and to CW. Ruth subsequently called Desmond a Coward, after which Daddy Widmore sent his daughter to the Abbey on an errand that just happened to result in the two of them meeting.

Two years later, when Desmond "first" met Charles Widmore, the Great Man, after asking Des whether he had any military training, informed him that he wasn’t worthy of so much as a gulp of MacCutcheon’s, let alone the hand of his daughter.

When Widmore’s colleague, Ms Hawking convinced Desmond that his "path" was to break up with Penny, she called him a Coward just before she walked away.

Des then joins the Army - where one can "become a man you can be proud of" - and during his Basic Training, CW gives him Penny’s (correct) address so that he can visit her there and regain her love before he is dishonourably discharged - for cowardice (or insubordination) - from the Army .
Upon his discharge from Military Prison, CW is right there, outside the Prison and again accuses Des of cowardice as he offers to bribe him to stay away from Penny and then subsequently arranges for Libby to "give" Des the Elizabeth.

Despite the fact that her Daddy intercepted the letters that Des had sent her over the years, Penny still loved Desmond enough to track him down at the stadium in LA where Des tells Penny that he intends to win Widmore’s Sailboat Race to regain his honour.

IMO, it was CW, Ms Hawking and Libby - a Time Cop agent - who "nudged" Des onto The Elizabeth and thence onto the Island. The Implosion enabled Des’ mind to revisit his 1995 relationship with Penny and to "realise" (too late) that he could have chosen to stay with her ... and this Revelation sustained Desmond’s love - guided and supported by Daddy Widmore - enough for him to establish his Constant and thus enable Charlie to reach her briefly before his noble death. Note that CW, piggy-backing on Penny’s Listening Post info, set up the Kahana crew (including the MA-selected Science Team) and also including Naomi’s "cover story" Desmond photo.

In "Jughead", we see Desmond "break in" to the Widmore-sponsored Faraday lab where he conveniently "finds" the Daniel/Theresa photo and is then conveniently educated by the extremely-well-informed "caretaker" - and marches off to visit Theresa - which leads Desmond (by the nose) right back to Widmore - who once again suggests that Desmond should resume hiding after delivering his message to Faraday’s LA-located Mum.

It seems to me that Widmore’s careful emotional button-pushing is intended to propel Desmond (and therefore Penny and Young Charlie) into situations requiring Desmond’s Courage - which he will be that much more eager to demonstrate because his Father-in-law led him to do so.

In view of the fact that CW gave Desmond the correct LA address of Ms H, it seems to me that he either sent his daughter to her death (if she’s dead) or he used her as bait in an effort to have Ben killed. Either way, he sure is a Loving Daddy all the way.