David Poile gave up a 1st for Paul Gaustad about a decade ago, in what I think would be a similar situation. A guy that coaches and executives dream of having play on their PK and 4th line, but makes fans eyes gloss over most of the time.
IIRC Gaustad was a rental, too. They had maybe generally agreed that he would extend, but his contract was expiring. Glendening's deal still has term on it.
That was such a nuanced trade, though. Gaustad was statistically more of a low-end 3C who could also play the wing on a scoring line. He scored at a 31 point pace throughout his career prior to being traded to Nashville and was still being hyped as a guy that might have a 40 point season up his sleeve. He was also a perennial top faceoff guy and a distracting 6'5". He brought a lot more hype and excitement at the fan level than Glendening does. On a scale of Glendening to Draper, Gaustad was closer to Draper in terms of esteem.
Then you have to consider that Nashville was a top team when they traded for Gaustad but didn't really have the horses up front to compete in anything but a "win-by-committee" fashion. He was a great fit for that strategy, current and future. He was also one of the last guys traded at the deadline which leads me to believe there was either a bidding war or Nashville was highly desperate.
Either way, lots going on behind the scenes there. Only way I could see a comparable situation happening would be a deal specifically with Toronto because Babcock is so enamored by Glendening, they could use the PK/Faceoff help, and if Toronto loses out on the chance to bolster their defense with a sound positional defenseman, they could get desperate for a cheap, steadying addition that will assist the defense up front.
Glen with some retention + our 2019 3rd for TML's 2019 1st doesn't seem outlandish then.
