So the Chief will get some lawyer-written apology letter, and Doug will go on hinting that he didn't really mean the apology and coming as close as he can to renewing the alleged libel.
Should the Chief let things drop or proceed with a lawsuit?
He'd have grounds to proceed, for sure. As others have noted, even an apology only mitigates potential damages, it doesn't necessarily end the matter.
If I were the chief, though, I'd just move on. First off, Doug's statements were (no doubt deliberately) couched vaguely in the first place. Things like "the top leadership of the police" (could be more than one person), "condoned this behavior". All he's really saying is the top people who are in charge of the police (who?) "condoned" the leaking. Absent evidence that the "leadership" began an investigation into the alleged leak, isn't this fair comment? Granted, the sniggering wink-wink "you know exactly what I'm talking about" certainly implied more. But it's not a slam-dunk case, and the argument could be made that it's fair comment. Furthermore, damages to the Chief are hard to quantify. If you're a prospective employer of the ex-Chief, are you going to say to yourself, well, he was accused of leaking stuff because he was against Ford therefore I won't hire him? Maybe. Maybe others would be more likely to hire him (or vote for him) if they knew he knew how to play hardball and choose a side. Being police chief in a big city is inherently a bit of a political job, and leaking things to the press really isn't unheard of for politicians (and considered at worst a venial sin). Even if every person in Canada believed that the Chief deliberately leaked the news of the subpoena because he didn't particularly like His Worship, does that really do any specific monetary damage to him? After all, as the Globe article pointed out, the brothers "have been claiming for close to a year now that, for one reason or another reason [...] the chief is out to get them." The Chief didn't sue over those repeated jabs at him--doesn't that imply he either didn't think they were libelous, or that it they were, they didn't cause any harm to him?
Remember
the last libel suit the Twinmayors faced: because the Defendant's comments were kind of vague and mealy-mouthed, the Plaintiff ended up paying the Defendants significant costs.
Nobody wins in a lawsuit except the lawyers, usually.
Living in "this great city" feels like I'm stuck in a very bad Veronica Mars episode.