With just over a month left before the first stage of the free agency cycle, Chicago Sky general manager Jeff Pagliocca and new head coach Tyler Marsh are facing one of the hardest decisions of the offseason: whether or not to re-sign guard Chennedy Carter. On paper, this might seem like a no-brainer. Carter led the Sky in scoring, averaging 17.5 points per game and offering a rare spark for the worst offense in the league. Without her attacking creativity, the Sky offense would have floundered through the latter half of the 2024 season with no true offensive threat. But Carter is not guaranteed to return to the Sky for the 2025 season. The guard is a restricted free agent, a status applied to four-year veterans of the WNBA when their contract expires. The Sky can extend a qualifying offer — a one-year contract with a base salary above her prior $76,535 salary from 2024 — to Carter during a 10-day window from Jan. 11-20. This is not a binding agreement. On Jan. 21, Carter can begin to negotiate with every other team in the league, who can extend multiyear offer sheets. The Sky will retain their right of first refusal, which means they can match any offer sheet that Carter receives and sign her to that contract. But if the Sky opts not to match those offers, Carter will be free to sign elsewhere on Feb. 1. The Sky still plan to extend a qualifying offer to initiate restricted free agency for Carter per a league source, but that is only the first step in offseason proceedings that could see Carter land somewhere besides Chicago for the 2025 season. So why are the Sky deliberating so heavily on re-signing Carter? Personality is one key factor for Carter, who was second in the league in flagrant fouls (3) last season while struggling to maintain cohesion with her teammates on and off the court. Carter’s volatility — and the outsized attention it demanded from the Sky staff — was a contributing factor to the imbalance in coaching attention that ultimately resulted in the firing of Teresa Weatherspoon, per a league source. This isn’t a new issue for Carter, who was suspended by the Atlanta Dream for fighting in 2021 and benched by the Los Angeles Sparks for “poor conduct” in 2022. Carter didn’t play in the 2023 season before joining the Sky in 2024 — and that signing came with the understanding that the guard still needed to rehabilitate her image in the league. Chicago Sky guard Chennedy Carter tries to make a pass while guarded by Dallas Wings guard Jacy Sheldon during the game at Wintrust Arena on June 20, 2024. (Eileen T. Meslar/Chicago Tribune) In an encapsulation of her well-known temperament, Carter received a “Good Temper Award” bonus from Wuhan Shengfan, her offseason club in the Women’s Chinese Basketball Association. The team released a public statement praising Carter for her “emotional management” and detailing a 10,000 yuan ($1,372) bonus given for limiting confrontation with referees and opposing players. None of this context should serve as a nonstarter in negotiations this winter. Carter, 26, is young and hungry to prove herself. She has made significant strides in her game readiness and on-court demeanor since her rookie season. And her talent is undeniable, making her a clear asset to the right team if she can keep herself physically on the court and mentally in the game. But for the Sky, it’s crucial to determine whether Carter can jell with the coaching psyche of new hire Tyler Marsh, who is known for his reserved demeanor. The question of fit extends to the basketball side of the equation. Despite her success in 2024, Carter doesn’t necessarily match the ideal prototype of a Sky backcourt player that Pagliocca has outlined throughout the offseason. At 5-foot-9, she’s a slightly undersized guard who struggles with switching defensively. And although she was the highest-scoring player on the roster last season, those points came from the wrong areas of the court. If the Sky want to compete next season, they have to start by shooting 3-pointers. The Sky averaged a league-worst 4.8 makes on 14.9 attempts from 3-point range last season, a staggeringly low rate of long-range shooting. As a result, the offense regularly became gummed up inside the arc as teams sagged off the 3-point line to body up rookie bigs Kamilla Cardoso and Angel Reese. Carter doesn’t offer a solution to this problem. She made only nine 3-pointers last season, averaging less than one attempt from 3-point range per game and shot only 29% from behind the arc. Carter has made fewer 3-pointers in her entire four-year WNBA career (24) than 52 other players in the league made last season alone. This shot profile doesn’t fit the needs of the Sky for next season when they will attempt to space the floor heavily behind the arc to give Cardoso and Reese room to breathe in the paint. 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Only 63.9% of their made baskets were assisted despite attempting to run an inside-out offense through their bigs. While Carter supplied the bulk of the team’s scoring, she did so by posting the fourth-highest usage rate (28.4) in the league. This means Carter used more than a quarter of the total offensive plays run by the Sky while she was on the floor. And she often opted to reject screens from Cardoso and Reese rather than utilizing them, a factor that contributed to her high rate of isolation plays. None of these factors align with how the Sky aims to play offense next season. That doesn’t mean Carter can’t work in a different system. If focused correctly, her on-ball creativity would be lethal in the pick-and-roll. Her ability to get to the rim is still a key factor in creating kick-out threes and establishing a two-player game with Cardoso. But all of these factors will inform how deep into their pocketbooks the Sky are willing to reach to re-sign Carter. And if the Sky are unwilling to offer Carter a lucrative deal — or ask her to change up her game too much — she could seek a new home in 2025.