When the calendar turned to December, the ever-popular trade deadline season began in the Ontario Hockey League (OHL). For Windsor Spitfires’ general manager (GM) Bill Bowler, it might be the toughest decision he’s had since he took over.
Over the last three seasons, Bowler has developed a reputation for being active during deadline season, which generally runs from early December until the annual trade deadline on Jan. 10. While he didn’t make any moves in his first season (2019-20), he went all-in for both 2021-22 and 2022-23.
The first resulted in a trip to the OHL Championship (losing to the Hamilton Bulldogs), while the latter saw them lose in a historic first-round sweep to the eighth-seeded Kitchener Rangers. Last season, they struggled, he “reshuffled the deck”, and they missed the playoffs entirely. This season, it’s similar to 2021-23 as they’re fighting for the top spot in the conference again. The question is – does he go “all-in” again? That may not be the best move. Let’s look at some options, starting with the least likely.
Option 1: Bowler Goes All-In Again
First, let’s get one thing out of the way – Bowler isn’t going into “sell” mode this season. He’s fighting for the top of the conference and division and most of his best assets are just 18 or 19 years old. So, we’re not going to include that. The next most “unlikely” category, not far off, is “going all-in.”
After going all-in for the 2022-23 campaign, including acquiring NHL prospects Shane Wright (Seattle Kraken) and Brett Harrison (Boston Bruins), Bowler was left with a nearly empty draft cupboard. It took the Spitfires almost an entire season to replenish their stock and it meant a very rough 2023-24 campaign that saw them finish second last in the OHL. Now, they’ve got enough second-, third-, and fourth-round picks through 2028 to be fairly comfortable with their stockpile. It’s not overflowing, but with multiple picks in some rounds, it’s workable.
If Bowler went all-in again, he would likely have to give up a highly-touted player such as 17-year-old forward Jack Nesbitt (2023 first-round), someone from the 2022 draft like forwards Cole Davis or A.J. Spellacy, or even 2024 first-overall pick forward Ethan Belchetz. The only one who might not be considered “untouchable” is Nesbitt and, even there, it would take a mind-blowing offer for Bowler not to hang up the phone immediately.
It has taken a long road, but the Spitfires are in a much better spot now than a season ago. While Bowler has developed a reputation for being slightly unpredictable, this isn’t the season to shock the league. If he wants to go all-in, that’s what 2025-26 is for.
Option 2: Bowler Stands Pat
In 2019-20, Bowler took over from long-time GM Warren Rychel, who was very active and not afraid to be blunt about it. Nobody knew how Bowler would act as the replacement but fans quickly saw that it was going to be a long-term process. He wasn’t the vocal guy that his mentor was and that took some adjusting.
Related: Warren Rychel Steps Down as Windsor Spitfires’ General Manager
At the January 2020 trade deadline, Bowler went quiet. He made no moves and stood pat to see how his roster would turn out. In this case, it wasn’t a bad idea as the COVID-19 pandemic hit in early March and the league shut down. Other teams made big moves at the deadline and, unfortunately, some were all for nothing.
While there’s no pandemic this season (knock on wood), Bowler has a team that could make some noise in the playoffs without him doing any tinkering. They have the talent with Belchetz, captain Liam Greentree (Los Angeles Kings), and sniper Ilya Protas (Washington Capitals) up front, plus veterans Tnias Mathurin and Anthony Cristoforo on defence, and veteran goaltender Joey Costanzo having a career season. Despite modest expectations to start the season, they’ve shown that their great start was no fluke.
In the Eastern Conference, multiple teams have already made big moves for the playoffs. In the West, the London Knights, Rangers, and the Spitfires have separated themselves from the rest of the pack. If others go all-in, Bowler’s best option might be to just sit back, watch the chaos unfold, and keep his assets for a big run in 2025-26. He’ll have most of his team returning and any playoff experience this season will go a long way.
Option 3: Bowler Buys a Bit
The most likely option is “buy a bit”, which feels like a happy medium between standing pat and going all-in. Bowler has the assets to send a few picks and/or depth players to bring in veterans who will help this team for this season and 2025-26. It doesn’t mean bringing in a star talent but someone who’s proven to be valuable and has the experience they may need in the postseason.
In 2021-22, he brought in forwards Alex Christopoulos and Jacob Maillet, who needed a change of scenery. They each cost a future fifth-round pick (Maillet cost an extra 12th, too) and they became vital parts of the team until they were moved last season. At last season’s deadline, he acquired Ottawa Senators’ prospect defenceman Djibril Toure for a future third-round pick and an eighth-round pick. He became an important part of the defence until he got injured late in the season. These are the kinds of moves that Bowler could make. They’re not going to shake up the league but they provide much-needed value.
The club also doesn’t want to alter the locker room chemistry too much. They’ve repeatedly said that the room is as tight as ever and the last thing Bowler wants to do is bring in a player who will disrupt that.
It’s been a fun season for the Spitfires and their fans. Nobody expected them to be going for home ice, let alone contending. However, this is where they are and now Bowler has to figure out which way to go at the deadline. While he knows this team better than anyone, the moves he makes (or lack thereof) could shape the team over the next few seasons. It’s going to be a difficult decision but one we’ll enjoy keeping an eye on.
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