Caleb Wilfinger

Deputy Editor
Google News
Caleb is a Deputy Editor at Pickswise who resides in Upper Manhattan and has spent time in Philadelphia and Washington, D.C. He has been handicapping various sports since 2018, including NFL, NCAAF, NBA, NCAAB, MLB and tennis. The futures market is his favorite to target and he has a passion for sharing his plays with the Pickswise community.
Live Picks 9
Live Parlays 0
Weekly News Articles 8
Location
New York
Favorite Sports
Favorite Teams
Kansas Jayhawks
Los Angeles Dodgers
New York Giants
New York Knicks
Greatest Betting Win
One of my favorite sports betting memories was certainly in October of 2022, when I successfully cashed a 5-team Round Robin parlay involving games I had already played as straight bets. It involved Penn State catching 16 at home against Ohio State, along with Notre Dame, UCF, Louisville and Baylor all on the money line as underdogs. The Irish and Cardinals took care of business early by crushing their opponents and Penn State hung tough to cover the inflated number against the Buckeyes. Meanwhile UCF pulled out a thriller against Cincinnati, leaving me only a Baylor victory away from a serious 50U profit. Thankfully, the Bears made quick work of Texas Tech in the second half and I was able to watch the 4th quarter with a smile on my face. This was one of three 5-leg Round Robin parlays I cashed during the 2022 college football campaign, as part of what was a terrific season on the gridiron.
Greatest Achievements
Finished with a win rate of 63% in weekly 2022 NCAAF best bets column, highlighted by an 8-0 run to close out championship week and bowl season 25-8 (76%) YRFI/NRFI run from June through August 2023.
Education
Caleb attended Penn State University, where he covered Penn State football and basketball for 3 years (along with many other sports), getting an up close and personal look at the grind of a full collegiate athletics regular season. His two bachelor's degrees were in Journalism & Political Science, with sports journalism as a primary focus. During his senior year, Caleb began moving away from betting casually and turning into a sharper bettor, including creating systems, compiling data for multiple sports, etc.
Experience
5+ years betting experience 3+ years as a sports handicapper 10+ years as a sports journalist Caleb has been betting legally since 2019 but his history with gambling predates that, as he regularly picked NFL games against the spread throughout his college tenure. In 2021, Caleb started handicapping college football games for Pickswise and turned a profit for the season. After moving into a full-time Deputy Editor role in 2022, Caleb has had plenty of success and winners for the site’s users, most notably in college football, NFL and the MLB YRFI/NRFI market.
Favorite betting market / type
Futures and Point Spreads.
Favorite bookmakers
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Caleb's Picks

Game Totals Pick
Under 45.0(-110)

Regardless of which team covers the spread on Saturday, my favorite bet on this game is on the under at the current number. The Eagles have been a money printer to the under this season, as games involving Philadelphia have gone under the total in 6 consecutive contests. There is something to be said for the fact that the Eagles defense is an elite unit, and Vic Fangio’s group should be able to bottle up the Washington offense on the ground, which should force Mariota and company into obvious passing situations on 3rd and long. Conversely, the Eagles offense has been largely unreliable in recent weeks, and it’s hard to trust Hurts and a stale offensive scheme to produce against a division rival on the road. Let’s go with the under while it’s still above the key number of 44.

Under 45 available at time of publishing. Playable to 44.5

Anytime Touchdown Scorer Pick
J. Smith-Njigba (SEA) to score a TD(+115)

You’d be hard-pressed to find a more productive receiver than Jaxon Smith-Njigba this season. The Ohio State product is playing like a first team All-Pro in 2025, and he could potentially even putting his name into the Offensive Player of the Year conversation given his performances over the past couple of months. The Seahawks top wide receiver has tallied 4 touchdowns over the last 4 weeks, and he also saw great success against the Rams a few weeks ago, a game in which he finished with 9 receptions and 105 receiving yards. We can expect his connection with Sam Darnold to be strong once again on Sunday, especially since this is a favorable matchup against a secondary that this Seattle offense should be familiar with. While this is a pretty safe pick, I can’t ignore how good Smith-Njigba has been all season long.

Game Totals Pick
Over 46.5(-110)

Regardless of which team comes out on top on Saturday, the over is my preferred look on the total. While the Bears defense is improved, this is still a unit that has thrived on turnovers and has largely been unable to slow down competent opponents on a down-to-down basis this season. With that in mind, the Packers should be able to generate plenty of success in this game, even if Watson ends up sitting this one out. On the other side, the Bears offense has been absolutely rolling of late and Ben Johnson’s group is averaging nearly 27 points per game over the last four weeks. Let’s take the over in a matchup that could certainly produce some fireworks.

Over 46.5 available at time of publishing. Playable to 47.

Game Totals Pick
Under 47.5(-110)

Regardless of which team covers the spread on Saturday, the under is my preferred look on the total in this contest. Both teams have the capability to score, but the weather conditions might not be conducive to points in this one — as scattered showers and winds of 8-12 miles per hour are in the forecast at the time of writing. Oregon will likely look to establish a lead early on before focusing on bleeding out the clock in the second half. The Ducks have been a run-first team in recent weeks given all of their injuries at wide receiver, and I can’t expect that to change here with Texas Tech looming on deck. On the other side, while the James Madison defense should generate a few stops in this one, the offense likely won’t be able to throw the ball downfield against an excellent Oregon secondary (9th in passing success rate allowed). With that in mind, I’ll hone in on the under in a game that has the potential to be in the mid 40s.

Under 47.5 available at time of publishing. Playable to 47.

Point Spread Pick
WAS Commanders +7.0(-110)

One of the two games on Saturday’s NFL Week 16 slate comes in the NFC East, where the Eagles are set to take on the Commanders in the first of a pair of games over the final few weeks of the season. Philadelphia appeared to finally have its “get right” game a week ago, but it was against a Raiders team that is probably the worst outfit in football at the moment, so it’s hard to properly assess just how well the Eagles are playing at the moment. What we do know is that Philadelphia has largely struggled to consistently score for most of the season, and it’s actually the run game that has continued to underperform against expectations. This is the worst rush attack that the Eagles have had in years, and it’s certainly worth examining if Philadelphia will be able to continue winning without having a successful ground game. After all, it’s not as if Jalen Hurts is playing his best football at the moment, so the Eagles below average passing game shouldn’t be expected to have much success on the road in a divisional game.

On the other side, Washington is without Jayden Daniels for the remainder of the season, but Marcus Mariota has been effective as a backup quarterback when called upon this season. Just last week, the Commanders knocked off the Giants as short road underdogs, and the offense was surprisingly competent given the injuries that Washington has sustained to this point. With that in mind, even if the Commanders fall behind in this game, we can still count on Mariota and this offense to fight and stay within striking distance against an opponent that has struggled to win by margin all season long. I’ll take the full touchdown with the home team.

Eagles vs Commanders prediction: Commanders +7 available at time of publishing. Playable at that number. 

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Anytime Touchdown Scorer Pick
K. Williams (LAR) to score a TD(+125)

On the Los Angeles side of things, the Rams offense has been one of the best in football all season long, and we can expect another solid showing on Thursday. Even against an excellent Seattle defense, there should be avenues for the Rams to see success on the ground and through the air. That’s where Kyren Williams comes in, as the dependable Rams running back has 10 touchdowns on the season while averaging just under 5 yards per carry in the process. Williams can also catch passes out of the backfield, which could come into play against a Seattle defense that should look to heat up Matthew Stafford and make things uncomfortable for the Rams downfield passing game. Look for Williams to find the end zone for a fourth consecutive contest on Thursday.

Money Line Pick
CHI Bears Win(+100)

One of the most consequential games on the NFL Week 16 slate comes in Chicago, where the Bears are going to take on the Green Bay Packers in a massive showdown in the NFC North. These teams just met two weeks ago in Green Bay, and the Packers were able to come out on top in a game that came down to the final possession. This time around, Chicago is in a much better position as a team, and I actually make the Bears a small favorite in this game given the key injuries that Green Bay has sustained in recent weeks. Ben Johnson’s group was just in a very difficult situational spot against the Browns a week ago, and this offense didn’t miss a beat against the stout Cleveland defense, as Chicago racked up 31 points and dominated the game from start to finish at home. Caleb Williams is playing the best football of his young NFL career at the moment, while the Bears defense has shown signs of improvement of late. Given the fact that Chicago came up just a few yards short of sending the previous meeting between these teams to overtime, it’s hard not to favor Williams and company to pick up a possible division-clinching win at home.

While Chicago has impressed me in recent weeks, the Packers are a team that I’ll be looking to fade in the immediate future, albeit through no fault of their own. Green Bay is still one of the best teams in the NFC, but the Packers’ hopes of winning a Super Bowl were essentially dashed a week ago when Micah Parsons went down with a torn ACL in a loss to the Broncos. The rest of the Green Bay defense is still very solid, but it’s hard to quantify just how much of a difference-maker Parsons is in a variety of areas. Elsewhere, the Packers might also be without top wide receiver Christian Watson in this game, and that doesn’t bode well for Jordan Love’s downfield passing efficiency against an opportunistic Bears secondary that has made a living on forcing turnovers this season. I’ll back the home ‘dog while I’m still getting plus-money in what should be a terrific game on Saturday.

Packers vs Bears prediction: Bears ML (+100) available at time of publishing. Playable to -110.

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Point Spread Pick
James Madison +21.5(-110)

The final game of the opening round of the College Football Playoff will commence on Saturday evening from Autzen Stadium, as the Oregon Ducks are set to host the James Madison Dukes in a game that appears to be pretty lopsided on paper. This is the largest spread of any College Football Playoff game in this new 12-team format thus far, and all signs would traditionally point to the Ducks winning big and advancing to the quarterfinals in a few weeks. In all honesty, it wouldn’t surprise me at all if Dan Lanning’s team controlled this game from the opening kick and won by 17-20 points. However, even when pricing in an extra point or two for the atmosphere at Autzen Stadium at night in what should be one of the best Oregon crowds in recent memory, I just cant get to this number now that it’s currently sitting above 3 touchdowns.

This is a very difficult game to handicap given the impending coaching turnover on both sides, but I have massive respect for this James Madison coaching staff, and they should have their team ready to play in a game where the Dukes have nothing to lose and are playing with a bit of house money. In its only game against a Power 4 opponent on the road this season, James Madison was tied with Louisville in the 4th quarter and that was long before the Dukes were a finished product on offense. In fact, since Alonza Barnett III became the full-time quarterback, this has been a well-oiled machine (18th in success rate, 28th in EPA per play), albeit an offense that hasn’t faced a defense like what they’ll see against Oregon. Where JMU is pretty underrated nationally is on defense, as the Dukes are tops in the nation in success rate allowed, to go along with top 10 marks in EPA per play and points per drive allowed. They’ll certainly have their work cut out for them against an excellent Oregon offense, but the Ducks are still dealing with a number of injuries heading into this game and it’s not a guarantee that Will Stein’s offense will be at full strength, to say nothing of the focus concerns I have with the Ducks given both of their coordinators have already accepted other Power 4 head coaching jobs. Given the massive spread at play here, the backdoor could be wide open in the fourth quarter, and it’s not a guarantee that Oregon is just going to show up and win by 4 touchdowns on Saturday.  

James Madison vs Oregon prediction: James Madison +21.5 available at time of publishing. Playable at that number. 

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Heisman Trophy Winner Pick
D. Dampier to win Heisman Trophy(+6000)

This is a shot in the dark compared to some of the favorites on the board, but it’s an educated wager on a quarterback that I could see making a major leap this fall. Devon Dampier electrified the Mountain West at New Mexico a season ago, racking up 31 total touchdowns (including a whopping 19 touchdowns on the ground) in a season that saw him take a major step forward from his freshman campaign.

Now, the 3rd-year starter steps into a promising situation with a Utah team that handed the reins over to former New Mexico offensive coordinator Jason Beck, a respected offensive mind and a surefire upgrade from what the Utes had last season. The Utes also upgraded their weapons on the perimeter via the transfer portal and get a pretty favorable schedule compared to a few other contenders in the Big 12. I’ve got Utah favored in 11 games and if the Utes are able to navigate their way through a couple of tricky conference games, they should certainly find themselves in the Big 12 title game come Championship Weekend. That alone gives this 60-1 ticket a ton of value, so Dampier is worth a sprinkle at this number.

Caleb's Analysis