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 7
Live Parlays 1
Weekly News Articles 10
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 34.5(-110)

There are plenty of factors that point me in the direction of the under. For starters, Pittsburgh is going to be without DK Metcalf in this game, as the Steelers’ top wideout is suspended for the final 2 games of the regular season. Given the fact that this is going to be an extremely difficult matchup against a stout Cleveland defense on the road, it would be reasonable to expect that Pittsburgh struggles to score points in this one. On the other side, the Browns offense has not exactly been the picture of efficiency all season long and I wouldn’t expect that to change with high, sustained winds in the forecast for Sunday. The under is the only way I can look in this one.

Under 34.5 available at time of publishing. Playable to 34.

Point Spread Pick
NO Saints -2.5(-115)

While most of the Week 17 slate features at least one team in playoff contention, Sunday’s contest between the Saints and Titans is not one that most NFL fans will focus on. However, there is still a bit of value to be had in this game, and it comes on the visitors. The betting market has slowly adjusted to the Saints’ improved play over the second half of the season in recent weeks, and New Orleans continued its good run of form a week ago in a 29-6 victory over the lowly Jets. The victory marked the 3rd consecutive win for the Saints, and it was also the 4th straight game in which New Orleans covered the spread.

The insertion of Tyler Shough at quarterback has proven to be a significant upgrade over Spencer Rattler for an offense that was in desperate need of a spark, and the Saints rookie QB is also coming off the best game of his young career in that victory over New York last week. This momentum should carry over into this week’s matchup against a Titans defense that is dealing with some injuries to key players heading into this one. As for Tennessee, the Titans have showed signs of life in recent weeks, most recently in a win over the reeling Chiefs a week ago. However, Kansas City was already eliminated heading into that game and had nothing to play for. To make matters worse, the Titans defense got to face a 3rd-string quarterback for a decent chunk of that contest. It won’t be nearly as easy of a matchup for Tennessee this time around. I’ll lay the points with a New Orleans team that is trending up at the moment.

Saints vs Titans prediction: Saints -2.5 available at time of publishing. Playable at that number. 

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Point Spread PickBest Bet
IND Colts +6.5(-110)

Jacksonville has made an impressive jump in its first season with Liam Coen as head coach, clinching its first playoff berth since 2022. The Jaguars extended their winning streak to 6 games after an impressive 34-20 victory at Denver last Sunday as 3.5-point underdogs. During this hot stretch, the Jags have scored at least 34 points 4 times and have topped the 25-point mark all six games. In fact, Jacksonville has posted more than 25 points in eight consecutive games after getting held to 19 points in a pair of October losses to the Rams and Seahawks. In the last 2 weeks, QB Trevor Lawrence has tossed 8 touchdown passes and is riding a 6-game streak with multiple TD passes.

The Colts (8-7) have seen their dreams of a division title, much less a playoff spot crumble over the last two months. Indianapolis leapt out to an incredible 7-1 record in Daniel Jones’ first season as starting QB of the Colts. However, the Colts have lost six of the past seven games and lost Jones for the season with a broken fibula suffered in a 36-19 defeat at Jacksonville in Week 14. Indianapolis turned to 44-year old Philip Rivers to try and save its season, but the Colts have lost in his first two starts to the Seahawks and 49ers.

Rivers helped the Colts cover as 13-point road underdogs in an 18-16 defeat two weeks ago, but he threw for 120 yards. He looked better in Monday’s 48-27 blowout loss to San Francisco, posting 277 passing yards and 2 touchdowns, but the Colts’ defense had its worst performance of the season in their second home setback. This has been a series dominated by the home team, as the Colts are 4-1 in the past five against the Jaguars at Lucas Oil Stadium. Jacksonville is the team to beat in the AFC South, but Indianapolis should give them a run here looking for revenge for the loss a few weeks ago.

Jaguars vs Colts prediction: Colts +6.5 available at time of publishing. Playable to +6

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Game Totals Pick
Under 39.5(-110)

This total has dropped a few points since the open, and it’s easy to see why. The Titans offense has showed a bit of a pulse in recent weeks, but this is still a unit that grades out as one of the worst offenses in football (30th in EPA per play, 31st in success rate) and it’s hard to see Cam Ward and company putting up a big number in rainy and windy conditions on Sunday. On the other side, the Saints offense has tallied at least 20 points in 3 consecutive games. However, those performances came in advantageous environments where scoring conditions were much more optimal than what we’re expected to see in this contest. It’s not my favorite play on the board by any means, but the under is the only way I can look in this one.

Under 39.5 available at time of publishing. Playable at that number.

Point Spread Pick
CLE Browns +3.5(-105)

One of the more interesting games on the NFL Week 17 card comes in Cleveland, where the Browns are set to take on the Steelers in an AFC North showdown. Cleveland has shown flashes since the insertion of Shedeur Sanders at quarterback, and despite the fact that the rookie played a very poor game a week ago, the Browns still covered the spread against the Bills as home underdogs with relative ease. Not only is Buffalo a much better offense than what Cleveland will see against Pittsburgh this week, but this is not a good situational spot for a Steelers team that is coming off a trio of massive victories over the Lions, Dolphins and Ravens in recent weeks. Pittsburgh went from being on the outside looking in, to now clearly in the driver’s seat for the AFC North Crown and a first round home game in the AFC playoffs come January. The Steelers don’t even need to win this game in order to clinch the division, as a loss from the shorthanded Ravens would also do the trick. With that in mind, it’s reasonable to expect that Pittsburgh might not be at its sharpest this week against the lowly Browns.

Cleveland has been a tale of two teams this season. At home, the Browns have been one of the most profitable teams against the spread over the last 3 seasons, and it all starts with a defense that has been able to make life very difficult for opposing quarterbacks. In fact, the Browns just held down the Bills offense a week ago, so the Steelers shouldn’t be as much of a challenge in comparison. This is also a game where the weather figures to be a major factor, as we should see significant sustained winds in Cleveland once again. All signs point to this being a very close game, so I’ll gladly grab the points with the home ‘dog on Sunday.

Steelers vs Browns prediction: Browns +3.5 available at time of publishing. Playable to +3

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Point Spread Pick
PHI Eagles +1.0(-110)

The Philadelphia Eagles (10-5) are the only team to clinch a division title so far, wrapping up the NFC East after a 29-18 triumph at Washington last Saturday. The defending champions have rebounded nicely from a 3-game slide to win their last two games by double-digits, although they faced the Commanders and Raiders, who are not going to the playoffs. Philadelphia travels to Buffalo on Sunday seeking its 6th road victory of the season as the Eagles are listed as an underdog for the first time since last season’s Super Bowl.

The Bills (11-4) may not win their 6th straight AFC East crown, but Buffalo has shown it will be dangerous in the postseason. Buffalo is back home after rallying to shock New England two weeks ago and holding off Cleveland last Sunday to extend its winning streak to 4 games. The Bills were in a prime position to cover as 10.5-point road favorites last week against the Browns, leading 23-10 in the third quarter before Cleveland scored the final 10 points. Since Week 6, the Bills have not gone consecutive weeks without covering the spread, posting a 4-0 ATS mark in this situation.

The Eagles allowed the Giants to score 34 points in a Week 6 loss, but Philadelphia has not given up more than 24 points in nine consecutive games. The Bills have yielded at least 30 points in 4 of the past 6 games, including 32 points to the Buccaneers and 34 points to the Bengals. Buffalo has won in each of its 2 opportunities as a favorite of 3 points or less, but this is a short number against a Philadelphia team that has already clinched a division title.

Eagles vs Bills prediction: Eagles +1 available at time of publishing. Playable to Eagles ML (-110)

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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 Parlays

Friday's NBA Parlay
Yesterday
Toronto Raptors
Washington Wizards
TOR Raptors @ WAS Wizards · Game Totals
Under 227.5
Our Analysis

The Toronto Raptors have been involved in some very low scoring games of late, with 7 of their last 8 games coming in under the combined 227-point mark. That is hardly surprising since, in 6 of those games, they or the opposing team were held below 101 points. We could see a similar outcome when they visit the Washington Wizards tonight. Over the last 10 games, the visitors are dead last in offensive rating and true shooting percentage. With the Wizards in the bottom 10 in both categories, this one looks set to be an offensive slugfest. The Raptors also happen to be 9th in defensive rating during that stretch. With injuries to RJ Barrett and Jakob Poeltl, we should see Ochai Agbadji and Sandro Mamukelashvili start for them. The pair are 3rd and 4th on the team’s roster in defensive rating and should help the starting unit generate stops tonight.

Despite boasting some exciting young talent, the Wizards do not tend to push the tempo, ranking just 19th over the last 10 games in pace. The Raptors are not much better in that category, being 28th in the league. The hosts have also struggled from beyond the arc of late, making just 32.7% of their 3-point attempts during that stretch of games. This season the visitors the 3rd best team in defending the 3-point line, allowing opponents to make just 33.7% of their shots from deep. This is not the team that you can expect the Wizards to have a shooting resurgence against. Back the under with confidence as a result.

Raptors vs Wizards prediction: Under 227.5 (-110) available at time of publishing. Playable to under 225.

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Milwaukee Bucks
Memphis Grizzlies
MIL Bucks @ MEM Grizzlies · Point Spread
MIL Bucks +5.5
Our Analysis

The day after Christmas will feature an East versus West matchup when the Milwaukee Bucks take on the Memphis Grizzlies. The Bucks have a record of 12-18 and are only 4-10 on the road. Milwaukee has lost 3 of its last 4 games, but the Bucks did win their last game against the Indiana Pacers 111-94. Kevin Porter Jr. led the team with 24 points and 5 assists, and the Bucks held their opponent to 41% shooting and 26% from three.

The Grizzlies have a record of 14-16 and a home record of 6-8. Memphis has lost 2 of their its 3 games, but they are coming off a 137-128 win over the Utah Jazz. Santi Aldama led the Grizzlies in scoring with 37 points. It is the second time Aldama has scored 37 points in his last 3 games. He also scored 37 against the Washington Wizards on December 20th. 

Both the Bucks and the Grizzlies are trying to work their way back to .500 in spite of some key injuries on both sides. Giannis Antetokounmpo is getting closer to making his return to the floor, but he will miss another game tonight. The Grizzlies will be without Zach Edey, Ty Jerome, Brandon Clarke, and Vince Williams Jr. tonight. Ja Morant is still listed as questionable to return from an ankle injury tonight. With injuries to their top players, each team has needed their younger talent to step up. The Bucks have found a duo of scoring guards with Porter Jr. and Ryan Rollins. The pair is averaging a combined 37.6 points per game this season. Meanwhile, the Grizzlies have seen Aldama step up. In his last game, Aldama hit a career-best 7 threes against Utah. They also benefitted from 18 points from GG Jackson II in his first start of the season after being called up from the G League. With Bobby Portis and Myles Turner being able to match up against Jaren Jackson Jr. and Aldama, I don’t see any advantage that either team has over the other. I will side with the Bucks and the points. 

Bucks vs Grizzlies prediction: Milwaukee Bucks +5.5 is available at the time of publishing. Playable at that number.

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Caleb's Analysis