Not too long after the WNBA Draft night was over, the Chicago Sky’s decisions involving Angel Reese over the last couple of years came back to haunt them, especially with how everything turned out on the momentous night. This fumble left some league legends like Candace Parker and Aliyah Boston speechless.

The two discussed the absurdity of the situation on their Post Moves podcast, highlighting how Chicago’s decisions in 2024 gave way to Minnesota getting the second pick.

“The Lynx acquired Chicago’s pick in a last-minute trade on the eve of the draft two years ago, in 2024. The Sky sent a package of draft capital to Minnesota in order to jump up to number seven in that year’s draft and select Angel Reese,” said Parker. “So, this is why I say you have to wait a couple years to rate drafts trades because you traded Angel Reese. So basically, you got two first-round picks, right? In consecutive years, but you gave up this year’s pick, in which to me, Olivia Miles is a franchise changer. That’s crazy.”

The WNBA Draft ensures the worst-performing teams get a chance at a higher pick. So when the Minnesota Lynx drafted Olivia Miles as the second pick, it defied the entire system and left everyone wondering.

This strengthens the Lynx roster multifold, with the Minnesota franchise adding a scoring phenom to a team that led the league in scoring (86.1 points per game).

In 2024, Chicago traded with Minnesota to climb up the draft board to get Angel Reese. In that trade, the Lynx gained the option to swap the teams’ 2026 first-round picks. The 2026 WNBA Draft lottery happened in November 2025, taking into account performances over the last two seasons, and put Chicago’s pick at second.

Olivia Miles is coming off a trail-blazing 2025-26 campaign, setting multiple program records at TCU. She averaged 33.4 PRA (points, rebounds, and assists) per game in her final college basketball year, and finished her college career in the top-3 list of players with most triple-doubles (12).

She also became the only player in NCAA history to average 19 points, 7 rebounds, and 6 assists per game in a single season. Adding such an overall player would have helped Chicago with its new ‘win-now’ mentality. And while the Sky might think others are better options, handing them over to league leaders Minnesota is criminal.

However, this also highlights the Chicago front office’s dealings. The Sky traded the very player they gave up this swap option for this offseason, with Angel Reese now part of the Atlanta Dream roster. Also, the franchise had already converted the swap option into an outright pick in a more recent trade with Minnesota in 2025.

Not only did Chicago lose the prospect of a second pick in a top-heavy 2026 draft, but they also traded away the ‘franchise player’ they had climbed up on the 2024 board for. All they received from this entire Angel Reese saga were a few picks and ended up strengthening the league leaders.

While this whole situation points fingers directly at the Chicago front office, General Manager Jeff Pagliocca has provided his reasoning behind every Sky move this offseason.

Jeff Pagliocca highlights ‘win-now’ purpose behind offseason frenzy

As the dust settles on a frenetic offseason for the Chicago faithful, the moves have received mixed reactions from even the most hardcore fans. From trading away a ‘cornerstone’ star for future draft picks to their decisions on the 2026 WNBA Draft night, several questions have been raised about the thought behind these moves.

Jeff Pagliocca, though, is adamant that the front office has a ‘win-now’ mentality this year and has strengthened the roster accordingly. While the signing of seven-time All-Star Skylar Diggins shows their intent to compete for the top spots, he highlighted the importance of building an immediately competitive roster around the 35-year-old behind the moves to bring in Rickea Jackson, Jacy Sheldon, and DiJonai Carrington.

Pagliocca said, “We’ve had two losing seasons. So, you’re always trying to win now, as far as I’m concerned… I don’t wanna deal with Skylar Diggins every night if she doesn’t have players she cannot go to war with. So, we made sure that she understood the vision.”

Diggins is a serial winner with Team USA. Rickea is younger than Ariel Atkins but contributes similar numbers and is seen as a future All-Star. Jacy adds an efficient perimeter threat on offense while also beefing up defensive coverage.

Meanwhile, DiJonai is one of the few players to improve their contribution after coming into the WNBA. DiJonai will also add to the ‘win-now’ mentality, having reached the WNBA Finals previously with the Connecticut Sun.

Pagliocca labelled number 5 draft pick, Gabriela Jaquez, a ‘proven winner’, highlighting that the UCLA star’s mentality and three-level scoring ability make her a seamless fit into the Sky’s vision for this season.

Veteran Skylar Diggins has also highlighted her hunger to compete for the top spots after her arrival in Chicago. As many questioned her intent behind joining a Chicago team that has been rooted to the bottom for the last two years, Diggins admitted that, while being closer to home played a role in her decision, the 35-year-old intends to work equally hard as she always has.

“I’m not just coming here saying this is the end or whatever for me,” she said before adding. “I don’t think it’ll be a diminishing return. I’m committed to the work… I want to get better. That’s been my mantra since I was a kid, ‘get better.’ That’s the mindset I have here for this organization, for myself, and that’s the standard I hold myself to.”