OHL: Windsor Spitfires’ 2023-24 Trade Deadline Preview

Christmas is over, Santa has gone back to the North Pole, and the Windsor Spitfires have a big task in front of them. The 2023-24 Ontario Hockey League (OHL) Christmas trade freeze lifted this week, and now there are questions to be asked ahead of the upcoming trade deadline.

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General manager Bill Bowler hasn’t been one to shy away from making deadline headlines in the past. Two seasons ago, he went for broke, helping the team get to the OHL Championship (lost in Game 7 to Hamilton Bulldogs). Last season, he was all-in again, but they suffered a heartbreaking first-round loss to eighth-seeded Kitchener Rangers. Now, with his team fighting just to get into the playoffs, there’s a choice to be made ahead of the deadlines.

The Spitfires’ Options

This season’s overage (20-year-old) deadline is Tuesday, Jan. 9 at noon while the deadline for everyone else is Wednesday., Jan. 10 at noon. Let’s look at the options.

Option 1: Sell, Sell, Sell

The first option, and probably the most likely, is for Bowler to sell assets in order to build around the 2005-2007-born players (16-18-year-olds). The question is – who stays and who goes without disrupting the room?

Windsor Spitfires' GM Bill Bowler
Windsor Spitfires’ GM Bill Bowler. (David Jewell / The Hockey Writers)

Over the last two seasons, through trades and signings, Bowler built up the 18-and-19-year-olds on the roster. Those players are now 19 or 20 and are options to be traded during a rebuild. After last season, they had seven possible overage players, and teams can only keep three. They made a few moves and, following trades in November, wound up with defenceman Roberto Mancini, plus forwards Oliver Peer and Jacob Maillet. They also have several 19-year-old forwards – Ryan Abraham, Valentin Zhugin, Aidan Castle, Colton Smith, Ryan Struthers, and Noah Morneau – along with goaltender Ian Michelone. This gives them options to make moves.

While some of those listed wouldn’t likely be moved for more than a pick or two, players like Abraham, Peer, and Maillet could fetch more given their point-per-game track records. Michelone also had a much-improved December, showing what he can do with a confident group in front of him. If he was traded, they have 17-year-old Carter Froggett waiting in Junior B. He showed well in camp and then in a brief stint in November.

Hearing the word “selling” can scare fans. After back-to-back Western Conference regular season titles, they’ve had a taste of success, and it’s hard to put that drink down. However, selling and building around their young core can help ensure this club gets back to where everyone wants.

Option 2: Spitfires Reshuffle

Coming into the season, it was expected that the Spitfires would rebuild and go into sell mode as they approached the deadline. However, it hasn’t quite worked out like that.

The November deal with the Saginaw Spirit that saw Mancini and Zhugin come to the Spitfires for fan favourites Alex Christopoulos and Rodwin Dionicio was more of a reshuffling of the roster than a true “sell.” While Bowler traded away plenty of offence, he got some offence and heavy defence in return, along with numerous picks, and the ages of the players coming and going were nearly identical. This seems like the kind of trade that could be made again.

Roberto Mancini Windsor Spitfires
Roberto Mancini of the Windsor Spitfires. (David Jewell / The Hockey Writers)

Bowler’s shown no hesitation to go all-in during his tenure but the willingness to go full rebuild hasn’t quite matched that. Instead, lateral (age-wise) moves that involve picks coming to the Spitfires may become the story at this deadline. It would be a unique approach and one that fans haven’t seen in a long time. Whether it’s good or not is to be determined.

Option 3: No Moves At All

This seems like a strange option given Bowler’s willingness to make moves over the last two seasons and even into this deadline, but it’s not abnormal for him.

During his first trade deadline in 2019-20, just before COVID-19 hit, Bowler was more of an observer. He made a small trade in November 2019 to get veteran defenceman Joseph Rupoli for a pick, but once the deadline approached, he did nothing else. Could that work now?

Windsor Spitfires' GM Bill Bowler
Windsor Spitfires general manager Bill Bowler in 2019-20. (Dave Jewell/THW)

Bowler’s already made multiple moves. On top of the Spirit deal, he’s sent out defenceman Nick DeAngelis, 19, for defenceman Conor Walton, 17, and multiple picks. He also brought in defenceman Connor Toms, 19, and forward Owen Outwater, 18, for picks. It’s possible that the heavy lifting has been done already.

Shortly after the moves, the club fired new head coach (previously long-time assistant) Jerrod Smith, promoted assistant Casey Torres to interim head coach, and saw assistant coach Andy Delmore and goaltending coach Michael Leighton both resign. While the team had just four wins in the first 21 games, the move and the trades seemed to spark the roster. Bowler joined Torres on the bench, and they went 6-4 leading up to the Christmas Break. The team is developing chemistry, the room appears to be as tight as ever, and the players are eager to get the second half underway.

Related: Windsor Spitfires Shake Roster, Make Trades with Spirit and Fronts

Watching other teams get into bidding wars or get lower-than-desired value for their stars isn’t the most entertaining option, but it wouldn’t be the worst thing. That way, they build on what they’ve accomplished over the last month, let their youth develop, and see how far it can take them.

Option 4: Bowler Becomes Buyer

This is the least likely of the options but one that can’t be ignored. In 2021, Bowler said that he wanted to be relevant every season despite how tough that is in the cyclical nature of junior hockey. While the team is currently last in the Western Conference, it doesn’t remove the option to become buyers just to get that final playoff spot.

According to the OHL Draft Pick Database, the Spitfires have multiple second-round picks and multiple fourth-round picks in 2024. They also have several younger players with potential – defenceman Anthony Cristoforo, 2023 first-round pick forward Jack Nesbitt, and 18-year-old goaltender Joey Costanzo, to name three – that could be moved if Bowler really wanted to upgrade a position.

Bowler has always done what he thought was best for the organization. Becoming the “all-in” buyer is highly unlikely this season given their lack of draft picks but, in theory, he could push the envelope to get the team into the playoffs. It’s a risky move that could frustrate fans in the long term, but it’s also one that could create a similar short-term “wow” factor that we saw in the last two seasons.

What Do the Spitfires Need?

All of this begs the question – what do they need? So far, Bowler’s acquired two veteran defensive defencemen (Toms and Mancini), a scoring forward (Zhugin), two future pieces (Outwater and Walton), and picks. What else is there?

1. An Impact 18-year-old Forward

When Bowler traded forwards Ethan Miedema and Christopher O’Flaherty, along with defenceman Bronson Ride, last January, he saw a good portion of his 2021 draft class fly out the door. He has 18-year-olds Ethan Martin and Jack Greenwell up front (along with Tanner Winegard, 18, on defence) from the draft, but neither one has become the impact player they need from that age. Martin has seen semi-regular ice time, but he’s been a fourth-line guy so far, and Greenwell is lucky to get into the lineup. They also brought in Outwater from the Kingston Frontenacs. The former North Bay Battalion first-round pick has potential but has just six points in 13 games since the trade.

There’s a strong need for an 18-year-old who can take the pressure off of the younger guys while providing protection in case an older player has a cold streak. It doesn’t require Bowler to go into “buy” mode, but those 18-year-olds will be a vital part of the roster next season. Right now, they can’t rely on Martin or Outwater to take control, so this would be a significant addition to the club’s future.

2. Offensive Veteran Defenceman

Last season, the Spitfires had Dionicio, DeAngelis, Michael Renwick, and Jacob Holmes as their primary veteran offensive weapons on the blue line. They combined for 116 points. Unfortunately, they’ve all been traded or graduated since the season ended.

Now, the club has been relying on Cristoforo (22 points in 31 games) and 17-year-old rookie Carson Woodall (11 points in 22 games) to do the offensive lifting on defence. They have Toms and Mancini as their older players back there, but while both have put up points in the past, neither is being counted on for that style of game. They also have Winegard, who had 55 points in 92 games in Junior B over the last two seasons. However, that hasn’t translated to the OHL, with just one assist in 21 games.

Anthony Cristoforo Windsor Spitfires
Windsor Spitfires’ defenceman Anthony Cristoforo. (David Jewell / The Hockey Writers)

This is why an 18- or 19-year-old offensive defenceman would be a great addition. It doesn’t have to be a superstar that will cost Bowler a young talent and multiple high picks. However, it should be someone who can be counted on in high-stress situations while they take some pressure off of Cristoforo and Woodall. Strangely, DeAngelis would have fit this role perfectly if they hadn’t traded him. Regardless, this is a group that needs some of the offensive pressure removed and have it done by someone who’s going to be around for more than a few months.

3. A 17-Year-Old Forward

The Spitfires’ 2022 Draft might have been one of the best in recent team history. From Cristoforo, Woodall, Froggett, Liam Greentree, A.J. Spellacy, Cole Davis, and potentially more, this draft has already shown it’s ready to burst. However, this is a perfect chance for Bowler to add to that nucleus.

Liam Greentree Windsor Spitfires
Windsor Spitfires’ forward Liam Greentree. (David Jewell / The Hockey Writers)

As we mentioned above, the club has several older guys that could be moved if they go into a rebuild. If they can’t bring in an 18-year-old, then getting a 17-year-old (2006-born) would be a big help. It doesn’t necessarily have to be someone who’s proven, but maybe a player who just wants a fresh start and significant ice. The club has a history of finding players who are looking for a big break (Peer, Maillet, and Christopoulos, for example) and repeating that success would be welcomed.

4. Draft Picks

While impact players are nice, Bowler could still use draft picks. That’s what happens when you go all-in for two straight seasons.

Since April, Bowler has done well in bringing in several draft picks through trades. As we mentioned earlier, according to the OHL Draft Pick Database, he has the Niagara IceDogs’ second-round pick in 2024, which should be higher in the round, plus the Peterborough Petes’ pick in the same round. He also has two-fourths in the same draft. However, there are holes in the cupboard that could use filling. He has nothing in the fifth or sixth rounds in 2024, no fourth-round pick in 2025, and no third-or-fifth-round picks in 2026 or 2027.

This isn’t an area of concern, at least compared to how it looked in the Summer. However, if there are picks offered that can fill in the gaps and create a full cupboard for the future, you take them and run.

Bowler Hires Newbury as Assistant Coach

With the freeze lifted and teams back in action for the second half, the Spitfires took care of some off-ice business this week. While Bowler has been doing his GM duties along with helping Torres behind the bench, that’s not going to be the case for long. On Christmas Eve (Sun., Dec. 24), he hired long-time OHL and NHL player Kris Newbury as an assistant coach.

Newbury played for the OHL’s Belleville Bulls (now Brantford Bulldogs via Hamilton Bulldogs) and Sarnia Sting from 1998-03 as a scrappy, offensive forward. He then had a lengthy pro career for multiple clubs until 2019, both in North America and in Europe, before joining the bench in 2021-22. Since that point, he’s been an assistant coach with the Trenton Golden Hawks Junior A, the head coach of the Greater Kingston Gaels Under-15 AAA, and, most recently, the head coach of the Quinte Red Devils Under-16 AAA.

This is a big move for the Spitfires because it allows Bowler to focus on his GM duties with the deadline coming up. This isn’t going to be an easy stretch for the team, but it should set them up nicely for the future.